Hotels in Winchester
Top landmarks in Winchester
Find out more about Winchester
What's Winchester like?
If you're looking to discover somewhere new, look no further than Winchester. Whether you're planning to stay for a night or for the week, the area around Winchester has accommodations to fit every need. Search for hotels in Winchester with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Winchester hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Winchester hotel deals are here with our lowest price guarantee.
Where are the best places to stay in Winchester?
Top hotel picks in and around Winchester:
Highland Lake Gorgeous Sunsets 3RD BAY East Side, Private Dock
Winsted waterfront vacation home with fireplace, kitchen- • Beach sun loungers • Garden • Walkable location
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Family-friendly Winsted vacation home with fireplace, kitchen- • Spa tub • Garden • Walkable location
Our Cottage - Small in size, Big in character, on beautiful Highland Lake
Lakefront Winsted accommodations with fireplace, kitchen- • Water park • Garden • Central location
Winchester Mountain House
Winsted beachfront vacation home with patio- • Ski-in/ski-out access • Walkable location
How to Get to Winchester
What are the closest airports to Winchester?
- • Bradley Intl. Airport (BDL), 21.5 mi (34.5 km) from central Winchester
- • Westfield, MA (BAF-Barnes Municipal), 26 mi (41.9 km) from central Winchester
- • Oxford, CT (OXC-Waterbury - Oxford), 30.7 mi (49.4 km) from central Winchester
Things to See and Do in Winchester
What is there to see in Winchester?
- • Highland Lake
- • Platt Hill State Park
- • Burr Pond State Park
What is there to do near Winchester:
- • Connecticut Valley Winery (7.3 mi/11.8 km from the city center)
- • Warner Theater (8.4 mi/13.5 km from the city center)
- • KidsPlay Museum (8.4 mi/13.5 km from the city center)
- • Norfolk Historical Museum (6.7 mi/10.8 km from the city center)
- • Jerram Winery (7 mi/11.3 km from the city center)
When is the best time to visit Winchester?
- • Hottest months: July, August, June, September (average 69°F)
- • Coldest months: January, February, December, March (average 31°F)
- • Rainiest months: October, May, June, and July (average 4 inches of rainfall)
Search places to stay by category
CheapBudget-friendly hotels and other affordable accommodation options- LuxuryFour- and five-star hotels with extra comfort and convenience
- Parking availableCar parking available at location
- KitchenSelf-catered rooms and properties equipped with kitchens or kitchenettes
- BeachHotels and resorts located on the beach or nearby
- Pet FriendlyDogs and other pets are welcome to stay
- PoolHotels with indoor or outdoor pools, plus rooms with private pool options
- Family-friendlyChild-friendly hotels, resorts, and other places to stay with kids
