Photo by Brian V. Rowe

Hotels in Shelter Island Heights

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May 11 - May 12
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Where to stay in Shelter Island Heights?

ⓘ Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Shelter Island Heights on Hotels.com. These Shelter Island Heights hotels consistently deliver on comfort, location, and value. Last updated on .

Lobby lounge
The Harbor Front Inn
The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (596 reviews)
Overlooking Greenport Harbor, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness center, and complimentary breakfast while exploring nearby attractions.
$267 nightly
The price is $305
May 19 - May 20
Total with taxes and fees
The Harbor Front Inn
Resort view
Sound View Greenport
Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (646 reviews)
Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railroad Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.
$351 nightly
The price is $401
May 27 - May 28
Total with taxes and fees
Sound View Greenport
Beach bar
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (152 reviews)
Silver Sands Motel & Beach Bungalows
Exterior
Zey Hotel
Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbor. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbor Brewing Company and Farmers' Market.
$203 nightly
The price is $231
May 19 - May 20
Total with taxes and fees
Zey Hotel
Property entrance
The Menhaden
The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (181 reviews)
Escape to this stylish Greenport retreat offering free breakfast and WiFi. Relax at the rooftop terrace or grab a drink from the bar before exploring local attractions on complimentary bikes. Only a 3-minute walk from Greenport Station, near Camera Obscura.
$426 nightly
The price is $481
May 19 - May 20
Total with taxes and fees
The Menhaden
Terrace/patio
The Pridwin Hotel
The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84 reviews)
Perched on the bay, this coastal retreat offers a private beach, outdoor pool, and spa with hydrotherapy treatments. The seasonal restaurant serves local cuisine while proximity to Crescent Beach and Sunset Beach enhances your island getaway.
$354 nightly
The price is $404
May 17 - May 18
Total with taxes and fees
The Pridwin Hotel
Exterior
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (268 reviews)
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.
$243 nightly
The price is $274
May 25 - May 26
Total with taxes and fees
The Shoals Suites and Slips
Terrace/patio
American Beech Hotel
American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (200 reviews)
Explore Greenport from this stylish inn with its welcoming bar and restaurant. Grab the complimentary bikes to visit nearby Greenport Harbor Brewing Company. The attentive staff and daily housekeeping ensure a carefree stay, just an 8-minute walk from the train station.
$310 nightly
The price is $354
May 12 - May 13
Total with taxes and fees
American Beech Hotel
Lobby sitting area
Hyatt Place Uncasville - Casino Area
Hyatt Place Uncasville - Casino Area
3.0 star property
Montville
9.2 out of 10, Wonderful, (2,695 reviews)
Steps from Mohegan Sun Casino and Arena, this hotel offers an indoor pool, 24-hour fitness center, and bar/lounge. Enjoy free breakfast, WiFi, and parking. Guests praise the comfortable beds and helpful staff.
$98 nightly
The price is $113
Jun 1 - Jun 2
Total with taxes and fees
Hyatt Place Uncasville - Casino Area
BBQ/picnic area
Fordham House
Fordham House
3.0 star property
Greenport
10.0 out of 10, Exceptional, (16 reviews)
Fordham House
Outdoor dining
Stirling House Bed & Breakfast
Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24 reviews)
Escape to this charming B&B on the bay, offering free breakfast, WiFi, and parking. Just an 11-minute walk from Greenport Station and near local attractions like Greenport Harbor Brewing Company and the Farmers' Market. Enjoy the terrace, bar, and deli.
$503 nightly
The price is $575
May 15 - May 16
Total with taxes and fees
Stirling House Bed & Breakfast
Front of property - evening/night
Shelter Island House
Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (57 reviews)
Tucked away in Shelter Island Heights, this golf-adjacent hotel offers a seasonal outdoor pool and rejuvenating massage services. Enjoy cocktails at the poolside bar, grab bites at the restaurant or deli, then explore nearby Sunset Beach and Shelter Island Country Club.
$201 nightly
The price is $230
May 17 - May 18
Total with taxes and fees
Shelter Island House
Restaurant
Oyster Estate
Oyster Estate
2.0 star property
Greenport
9.2 out of 10, Wonderful, (284 reviews)
Unwind at this North Fork retreat with a refreshing swim or soothing soak after exploring nearby museums. Complimentary bikes let you discover charming Greenport while free WiFi and parking add convenience to your coastal escape.
Oyster Estate
Restaurant
Sunset Beach Hotel
Sunset Beach Hotel
2.0 star property
Shelter Island
9.2 out of 10, Wonderful, (18 reviews)
Sunset Beach Hotel
Living area
Harbor Knoll Bed & Breakfast
Harbor Knoll Bed & Breakfast
3.0 star property
Pipes Cove
9.2 out of 10, Wonderful, (12 reviews)
This historic Greenport B&B offers a tranquil retreat with private pools and a welcoming bar/lounge. Just a 5-minute walk from Greenport Station and minutes from local museums, guests enjoy complimentary WiFi and parking during their coastal getaway.
Harbor Knoll Bed & Breakfast
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets
West Neck Guesthouse
West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very Good, (37 reviews)
Wake up to a fresh continental breakfast at this coastal B&B offering a seasonal outdoor pool and complimentary bicycles for island exploration. Located near Shelter Island Country Club and Sunset Beach, guests enjoy free WiFi and parking in this tranquil garden setting.
$219 nightly
The price is $250
May 31 - Jun 1
Total with taxes and fees
West Neck Guesthouse
Outdoor dining
The Chequit
The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (37 reviews)
Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.
The Chequit
Exterior
Arbor View House B&B
Arbor View House B&B
3.5 star property
East Marion
9.2 out of 10, Wonderful, (15 reviews)
Discover tranquility at this luxurious East Marion retreat featuring 2 hot tubs and garden views. Located near Island's End Golf and Country Club, this B&B offers complimentary breakfast and WiFi plus free parking for exploring nearby Truman's Beach.
Arbor View House B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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When is the best time to visit Shelter Island Heights?

Our prices for hotels in Shelter Island Heights are cheapest in February
Price trends for hotels in Shelter Island Heights
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Shelter Island Heights
May
High 59°F / low 53°F. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 59 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
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June, no crowd data, average high temperature 68 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
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July, no crowd data, average high temperature 76 degrees Fahrenheit, average low temperature 71 degrees Fahrenheit. Sunny most days.
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August, no crowd data, average high temperature 76 degrees Fahrenheit, average low temperature 71 degrees Fahrenheit. Sunny most days.
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September, no crowd data, average high temperature 71 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
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October, no crowd data, average high temperature 63 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
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November, no crowd data, average high temperature 54 degrees Fahrenheit, average low temperature 46 degrees Fahrenheit. Sunny most days.
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December, no crowd data, average high temperature 46 degrees Fahrenheit, average low temperature 38 degrees Fahrenheit. Cloudy most days.
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January, no crowd data, average high temperature 40 degrees Fahrenheit, average low temperature 31 degrees Fahrenheit. Partly sunny.
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February, no crowd data, average high temperature 40 degrees Fahrenheit, average low temperature 32 degrees Fahrenheit. Cloudy most days.
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March, no crowd data, average high temperature 43 degrees Fahrenheit, average low temperature 36 degrees Fahrenheit. Partly sunny.
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April, no crowd data, average high temperature 50 degrees Fahrenheit, average low temperature 44 degrees Fahrenheit. Sunny most days.
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Monthly weather averages (˚F)

Top neighborhoods in Shelter Island Heights

Photo by Erisa Dilo
Open Photo by Erisa Dilo

The Heights

The The Heights neighborhood has lots to see including Sunset Beach and Shelter Island Country Club.

view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water (shell bank creek)

Hay Beach

Shelter Island's Hay Beach neighborhood offers attractions including Menhadden Lane Beach.

Top landmarks in Shelter Island Heights

Crescent Beach

4.7/5 (13 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Crescent Beach located 1.2 mi (1.9 km) from central Shelter Island Heights. Catch the sunset by the shore at Sunset Beach, just a short walk away.
See properties

Learn more about Shelter Island Heights

Shelter Island Heights is well-known for its attractions such as Sunset Beach and Crescent Beach. This beachside city has something for everyone including sights like Shelter Island Country Club and Sylvester Manor.

See all hotels in Shelter Island Heights
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Check out reviews of Shelter Island Heights hotels guests love

Sound View Greenport

Sound View Greenport

4/10 Poor
"They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty."
Patricia 1-night trip
Posted 12 hours ago
Sound View Greenport

Frequently asked questions

What are the best hotels in Shelter Island Heights?

  • The Pridwin Hotel (4-star, guest rating: 9.6/10): This hotel is a standout with its beautiful, clean rooms and a fantastic location. Guests appreciate the amazing amenities, including a private sand beach and a full-service spa, making it perfect for relaxation. The delicious food and attentive staff further enhance the experience, ensuring a memorable stay.


  • House on Chase Creek (guest rating: 9.4/10): Known for its serene atmosphere and lovely lake views, this lodging offers easy access to local restaurants and the ferry. Guests enjoy the comforts of home, including free WiFi and a garden, making it a great choice for a tranquil getaway.


  • The Chequit (3-star, guest rating: 9.0/10): This charming hotel is pet-friendly and features connecting rooms, making it ideal for families or groups. With a restaurant and a coffee shop on-site, you can enjoy convenient dining options during your stay.


  • Shelter Island House (3-star, guest rating: 8.4/10): A family-friendly option, this hotel offers a seasonal outdoor pool and a complimentary continental breakfast. Guests appreciate the inviting bar/lounge and the relaxed atmosphere, perfect for unwinding after a day of exploring.


  • West Neck Guesthouse (3-star, guest rating: 8.0/10): This adults-only guesthouse is praised for its comfortable rooms and lovely outdoor pool. With easy parking and a peaceful garden area, it provides a cozy retreat for couples or solo travelers looking to relax.

How much is a Shelter Island Heights hotel?
You can find great-value hotel deals from $185 in Shelter Island Heights. No matter what type of trip you're planning, there are plenty of popular, affordable hotels to suit your needs and budget. To easily find affordable hotels in Shelter Island Heights, search on Hotels.com and then sort results by "Price: low to high".
Are there any last-minute deals on Shelter Island Heights hotel bookings?
Yes, travelers can find selected last-minute hotel deals in Shelter Island Heights on Hotels.com. To benefit from exclusive member prices and discounts, make sure you sign up to our Save Your Way rewards program, where members can save instantly with their discount or bank as rewards for a future trip.
What are the best hotels near Sunset Beach in Shelter Island Heights?

  • The Pridwin Hotel (4-star, guest rating 9.6/10): This hotel is an excellent choice for those looking to enjoy Sunset Beach, located just 0.6 miles away. Guests appreciate the beautiful and clean rooms, along with amazing amenities like a private sand beach and a full-service spa. The staff is known for their attentive service, making your stay even more enjoyable. With a delicious complimentary breakfast and a lovely pool, it's a great base for relaxation and beach activities.


  • House on Chase Creek (guest rating 9.4/10): Situated about 0.8 miles from Sunset Beach, this lodging offers a serene experience with lovely lake views. Guests praise its easy access to local restaurants and the ferry, making it convenient for exploring the area. The property features comfortable amenities like free WiFi and a garden, perfect for unwinding after a day at the beach.


  • The Chequit (3-star, guest rating 9.0/10): Also located around 0.8 miles from Sunset Beach, this charming hotel is known for its pet-friendly policy and connecting rooms, making it suitable for families or groups. With a coffee shop and a restaurant on-site, you can enjoy meals without venturing far. Guests appreciate the comfortable accommodations with premium bedding, ensuring a restful night after a day of sun and sand.


  • Shelter Island House (3-star, guest rating 8.4/10): Just 0.3 miles from Sunset Beach, this hotel is family-friendly and features a seasonal outdoor pool, perfect for cooling off after a beach day. Guests enjoy the complimentary continental breakfast and the inviting bar/lounge area. The property's location makes it easy to explore the nearby attractions while providing a comfortable retreat.


  • Sunset Beach Hotel (guest rating 9.2/10): Located a mere 0.1 miles from Sunset Beach, this hotel is ideal for a romantic getaway. Known for its luxury and pet-friendly atmosphere, it offers early check-in options, allowing you to maximize your beach time. The close proximity to the beach makes it a perfect choice for those looking to enjoy the sun and surf right at their doorstep.

What are the best hotels near Eastern Long Island Hospital in Shelter Island Heights?

  • The Menhaden (3-star, guest rating 9.6/10): This hotel is a fantastic choice for those visiting Eastern Long Island Hospital, located just 0.6 miles away. Guests consistently praise the friendly and helpful staff, making it a welcoming base for your stay. The property features a lounge, bar, and a rooftop terrace, perfect for relaxing after a day of appointments. With a focus on cleanliness, you can expect spotless accommodations throughout your visit.


  • Zey Hotel (3-star, guest rating 9.2/10): Situated only 0.4 miles from the hospital, Zey Hotel is known for its exceptional service and welcoming atmosphere. The location is ideal, with many restaurants within walking distance, making it easy to grab a meal. Guests appreciate the high standard of cleanliness and the availability of free WiFi and self-parking, enhancing your overall experience.


  • Greenporter Hotel (guest rating 9.2/10): Also located about 0.6 miles from Eastern Long Island Hospital, this hotel offers a relaxing pool area and a fitness center, perfect for unwinding after your hospital visits. Guests commend the friendly and accommodating staff, ensuring a pleasant stay. The property is well-maintained and provides free WiFi and self-parking for added convenience.


  • The Harbor Front Inn (3-star, guest rating 8.8/10): With a prime location just 0.6 miles from the hospital, this inn offers beautiful waterfront views and is within walking distance to shops and restaurants. Guests enjoy the clean and well-kept rooms, along with a complimentary breakfast that includes great coffee. The staff is known for their professionalism and engaging service, making your stay enjoyable.


  • Stirling House Bed & Breakfast (3-star, guest rating 9.8/10): Located 0.4 miles from the hospital, this charming bed and breakfast is praised for its delicious homemade breakfast options. The eco-certified property features a cozy atmosphere and offers free WiFi and self-parking. Guests appreciate the personal touch and attention to detail, making it a delightful choice for your stay.

What are the best areas to stay in Shelter Island Heights?

  • Shelter Island Heights (Main Street, Grand Avenue): This charming hamlet offers a relaxed, community feel with beautiful waterfront views. Staying here puts you close to local parks and scenic walking paths, perfect for leisurely strolls. Ideal for families and first-timers looking to enjoy a peaceful retreat.


  • Shelter Island (North Ferry Road, South Ferry Road): This area provides easy access to ferry services, making it convenient for exploring nearby destinations. The vibe is laid-back, with plenty of opportunities for outdoor activities. Great for couples and solo travelers seeking adventure and exploration.


  • Heights Beach (Heights Road): A picturesque spot known for its serene beach setting, perfect for sunbathing and swimming. Staying near Heights Beach allows you to enjoy the natural beauty of the area while being close to local amenities. Best suited for families and beach lovers looking for a relaxing getaway.

What practical tips should I know for visiting Shelter Island Heights?
When visiting Shelter Island Heights, staying connected is easy thanks to the availability of WiFi in public areas and many accommodations. If you need a local SIM card, you can find them at nearby convenience stores or mobile service providers, offering various data plans to suit your needs. Additionally, charging infrastructure is widely available in cafes and public spaces, allowing you to recharge your devices while you explore the area. It's also a good idea to pack a light rain jacket, especially if you're visiting in late spring or early summer when rainfall is more common. With these practical tips, you'll be well-prepared to enjoy your time in Shelter Island Heights.
Is free cancellation available on Hotels.com?
Most hotels on Hotels.com offer flexible booking with free cancellation, so you can receive a refund if you need to cancel. Free cancellation is available on selected hotels in Shelter Island Heights, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand. Cancellation fees may be applicable in some instances, so always read the booking terms before you make a reservation.
How to save on Shelter Island Heights hotel bookings?
Members save up to 20% on hundreds of thousands of hotels—it's free to sign up. When booking a hotel in Shelter Island Heights, you can choose how to use your savings on eligible stays. At checkout, either apply your member-only deal as an instant discount ("save now") or pay the full member price and bank your rewards to use on a future trip ("save for later").
Are all taxes and fees included in the Shelter Island Heights hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
What are the best areas for nightlife and entertainment in Shelter Island Heights?
Shelter Island Heights offers a vibrant nightlife scene with several key spots to enjoy. Sunset Beach is a popular choice, known for its lively vibe and stunning views, making it a great place to unwind after a day of exploring. For live music enthusiasts, Creekside at Sylvester Manor hosts regular performances, featuring notable artists and creating a lively atmosphere for music lovers. Additionally, Sylvester Manor Educational Farm provides a unique outdoor concert experience, perfect for those who appreciate music in a scenic setting. If you're looking for family-friendly evening activities, the area also boasts beautiful parks and waterfronts where you can take leisurely strolls or enjoy informal gatherings. Staying near these venues puts you in the heart of the action, allowing you to easily explore the diverse nightlife options available in Shelter Island Heights.
When is the best time to visit Shelter Island Heights?
The best time to visit Shelter Island Heights is from May to July, when the weather is warm and pleasant, making it ideal for outdoor activities and beach outings. July is particularly popular, attracting many travelers looking to enjoy the summer sun. If you prefer a quieter experience, consider visiting between February and April, when the crowds are fewer and the temperatures are cooler, ranging from 30°F to 40°F. Regardless of when you visit, packing a light rain jacket is advisable, especially in late spring and early summer when rainfall is more common. Staying in Shelter Island Heights during these peak months allows you to fully immerse yourself in the vibrant local culture and enjoy the beautiful coastal scenery.
What events or festivals can I catch while visiting Shelter Island Heights?
Shelter Island Heights hosts a variety of events that showcase local culture and entertainment, particularly during the summer months. One highlight is the concert series at Sylvester Manor, featuring performances like The James Hunter Six, which typically attracts a lively crowd. These concerts are a fantastic way to experience the local music scene and connect with fellow travelers and residents. Additionally, throughout the summer, you can find regular live music events at various venues, enhancing the vibrant nightlife and community feel of the area. Staying near Sylvester Manor puts you in a prime location to enjoy these cultural experiences and immerse yourself in the lively atmosphere of Shelter Island Heights.
What outdoor activities can I enjoy in Shelter Island Heights?
Shelter Island Heights offers a variety of outdoor activities that cater to all interests. You can explore the beautiful local beaches, such as Sunset Beach, which is just 1.7 miles away and is perfect for swimming, kayaking, and paddleboarding. If you prefer land activities, there are numerous hiking and cycling trails that allow you to immerse yourself in the stunning natural landscape. These trails are suitable for everyone, whether you're a casual walker or an avid cyclist. Additionally, many parks in the area feature playgrounds and picnic spots, making it a great destination for families looking to enjoy the outdoors together. Staying in Shelter Island Heights puts you right in the heart of these outdoor adventures, ensuring you have plenty of options to choose from during your visit.
What scenic spots should I visit near Shelter Island Heights?
When you're in Shelter Island Heights, there are several scenic spots worth visiting. One must-see location is the Hamptons Beaches, located approximately 14.2 miles away. These beaches are celebrated for their breathtaking views and are ideal for relaxation and outdoor activities. Another iconic landmark is Montauk Point, about 55.2 miles from Shelter Island Heights, which features a historic lighthouse and stunning coastal vistas perfect for photography. Additionally, don't miss the chance to catch a sunset at Sunset Beach, just 1.7 miles away, where the vibrant colors create a picturesque setting. Each of these locations offers unique experiences that enhance your stay in Shelter Island Heights, allowing you to appreciate the area's natural beauty.

Find out more about Shelter Island Heights

Embrace Tranquility: Unveiling the Natural Wonders of Shelter Island Heights

Nestled between the North and South Forks of Long Island, Shelter Island Heights offers a serene escape into nature’s embrace. With its picturesque beaches, like the charming Sunset Beach, and lush landscapes, this tranquil destination is perfect for romantic getaways or family vacations. Visitors can explore the island's scenic trails, indulge in luxury accommodations, or unwind in cozy vacation rentals. The captivating sunsets and peaceful ambiance make every moment unforgettable, inviting travelers to reconnect with nature and each other. Whether you’re seeking adventure or relaxation, Shelter Island Heights promises an idyllic retreat.

Discover great hotels near Shelter Island Heights

In Shelter Island Heights, you'll find a range of accommodations, from family-friendly hotels to charming bed and breakfasts. Whether you're seeking a luxurious retreat with stunning sunset views or a cozy spot close to the beach, there are plenty of options to make your stay enjoyable. Here are some of the best hotels near Shelter Island Heights that our travelers love:

  1. Harbor Knoll Bed & BreakfastOpens in a new window: This inviting 3.0-star Bed & Breakfast provides a perfect retreat for beach enthusiasts and golf lovers. With a remarkable guest rating of 9.2 out of 10, Harbor Knoll Bed & Breakfast offers direct beach access and a dedicated golf experience, ensuring leisure travelers can enjoy a relaxing getaway. The charming ambiance is enhanced by unique seasonal activities, like a Halloween parade and local shopping opportunities, making it an ideal spot for those seeking a picturesque escape.
  2. The Harbor Front InnOpens in a new window: A 3.5-star hotel with a guest rating of 8.8 out of 10, The Harbor Front Inn is a prime choice for travelers looking for a cozy and convenient stay. Featuring a warm and inviting lobby, this hotel is located just minutes away from a variety of restaurants and shops. Guests appreciate the comfortable rooms and helpful amenities, creating a welcoming atmosphere that enhances any visit to Shelter Island Heights. The continental breakfast and lovely lounge area add to the overall charm of this delightful property.
  3. The MenhadenOpens in a new window: With an impressive guest rating of 9.6 out of 10, The Menhaden is an exceptional 3.5-star destination for adventure seekers. This stylish hotel offers a variety of recreational activities, including hiking, kayaking, and ice skating nearby, catering to those who crave unique experiences. The modern design and thoughtful amenities, such as complimentary all-day refreshments, provide a luxurious touch to your stay. Travelers are sure to appreciate the attentive service and vibrant atmosphere, making it a standout choice for an unforgettable getaway.

Where to stay near Shelter Island Heights

Some of the best areas to stay in when visiting Shelter Island Heights are Greenport, Noyack, and Sag Harbor. Greenport offers nature and beautiful beaches, perfect for relaxation. Noyack is ideal for sailing enthusiasts and has a charming port atmosphere. Sag Harbor boasts a vibrant boating culture and rich history. For first-time visitors, Greenport is the best choice for a memorable stay.

  1. GreenportOpens in a new window: Greenport is a charming seaside village known for its natural beauty and vibrant arts scene. Nestled along the North Fork of Long Island, this area offers stunning waterfront views and fresh seafood. Visitors can explore picturesque parks, enjoy a leisurely bike ride along scenic paths, or visit local galleries showcasing works by talented artists. Greenport's bustling harbor is ideal for those who love nature and want to experience the area's maritime culture, making it a perfect base for your Shelter Island adventure.
  2. Sag HarborOpens in a new window: Sag Harbor is a historic whaling village filled with rich maritime heritage and a lively cultural atmosphere. This quaint community is dotted with charming boutiques, art galleries, and cultural attractions, perfect for those looking to soak in local creativity. Sag Harbor's beautiful waterfront and inviting parks offer great spots for relaxation, while its vibrant community events provide a taste of local life. It’s an excellent choice for travelers seeking a mix of history, art, and a warm community vibe.
  3. NoyackOpens in a new window: Noyack, a small hamlet near Sag Harbor, is well-known for its sailing opportunities and relaxed atmosphere. This area is perfect for water enthusiasts and those looking to unwind by the shore. Visitors can enjoy the serene beaches, explore nearby nature trails, or indulge in local shops that reflect the area's coastal charm. Noyack offers a peaceful retreat where you can appreciate the natural beauty of the region while still being close to the lively attractions of Sag Harbor.

Things to do in Shelter Island Heights

Shelter Island Heights enchants with its stunning coastal scenery and lush landscapes. Visitors can enjoy a variety of activities, from boating and hiking to whalewatching and golfing. With charming vacation rentals and luxury accommodations, it’s an ideal romantic getaway for those seeking relaxation amidst nature’s beauty.

  • Pollock-Krasner House and Study CenterOpens in a new window – Step into the world of modern art at this historic site, where renowned artists Jackson Pollock and Lee Krasner lived and worked. Explore their fascinating home and studio, where creativity flourished, and discover how their environment influenced their iconic masterpieces.
  • Orient Point County ParkOpens in a new window – Enjoy a breath of fresh air at this urban park, perfect for outdoor enthusiasts. Wander through scenic trails that lead to stunning views of the Long Island Sound, or pack a picnic and enjoy a relaxing day surrounded by nature's beauty.
  • Sag Harbor Marine ParkOpens in a new window – Visit this lively marina where you can watch boats come and go, or take a leisurely stroll along the waterfront. It's a great spot to soak in the maritime atmosphere and perhaps catch a glimpse of local fishermen at work.
  • Horton Lane BeachOpens in a new window – Spend a sunny afternoon at this beautiful beach, where you can build sandcastles, take a refreshing swim, or simply lounge on the shore. The gentle waves and serene surroundings make it an ideal spot for families and solo travelers alike.
  • 67 Steps BeachOpens in a new window – Discover this hidden gem, accessible by a charming staircase of 67 steps. Once you arrive, you'll be rewarded with breathtaking views and a peaceful atmosphere, making it a perfect location for a quiet escape or a picturesque sunset.

4 tips for savvy savings when booking a hotel in Shelter Island Heights

  1. Book for the cheapest times: The most budget-friendly time to visit Shelter Island Heights is from January to March, when hotel prices are typically lower. For a great value for money experience, consider staying for at least 2 to 3 days to fully explore the area's key landmarks and cultural attractions. During your visit, you can enjoy activities such as whalewatching, golfing, and attending performances at the local theater, as well as relaxing on the beach or taking a charming ferry ride. This timeframe not only offers affordable options but also allows you to immerse yourself in the rich history and natural beauty of the island.
  2. Look for last-minute deals on Hotels.com: If you're considering a trip to Shelter Island Heights, exploring the DealsOpens in a new window and Last-Minute DealsOpens in a new window sections on Hotels.com may lead you to discounted rates as your travel date approaches. By enabling email alerts or push notifications, you could stay informed about special promotions and flash sales. Additionally, the Smart ShoppingOpens in a new window feature on the app allows you to compare hotel prices and amenities, helping you find our best options based on your preferences. This way, you may discover your favorite hotels and uncover great midweek deals for your getaway.
  3. Be flexible with dates: Prices can fluctuate due to factors like the hotel's location, star rating, and the time of year, so having some flexibility with your travel dates may help you find a better deal on your stay in Shelter Island Heights. If you're in search of something unique, boutique hotels often provide a more personalized experience and could offer better value. When you book through Hotels.com, we'll inform you whether the price for your chosen dates is above or below the average. If the price is on the higher end, we may suggest alternative dates that could be more affordable to help you discover a great option.
  4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. For more budget-friendly options, consider looking for hotels in neighborhoods that are a bit further out, allowing you to balance cost with accessibility to the sites you want to see. You might also want to check out independent hotels located further away, as they usually tend to be more affordable and can offer a more authentic experience.

Best time to go to Shelter Island Heights

Shelter Island Heights experiences its lowest average temperature in January, at 35.6°F (2.0°C), while August is the hottest month, with an average temperature of 73.4°F (23.0°C). October are usually the wettest months. April, June, and July are the peak travel months in Shelter Island Heights, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, January, November, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny to mostly cloudy conditions.

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