Hotels in Windward Side

Photo by Meghan Watters

Hotels.com makes it easy and rewarding. Always

Reward yourself your way

Stay where you want, when you want, and get rewarded

Learn about Hotels.com Rewards

Unlock instant savings

You could get an extra 10% off with Member Prices

Sign up, it's free     Sign in

Free cancellation

Flexible bookings on most hotels*

Where to stay in Windward Side?

Top landmarks in Windward Side

Find out more about Windward Side

If you're looking to discover somewhere new, look no further than Windward Side. Whether you're planning to stay for a night or for the week, the area around Windward Side has accommodations to fit every need. Search for hotels in Windward Side with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Windward Side hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Windward Side hotel deals are here with our lowest price guarantee.

Frequently asked questions

What accommodations do travelers recommend in Windward Side?
Selera Dunia Boutique Hotel and El Momo Cottages are a couple of accommodations that are popular with guests.
Where can I find free parking with my stay in Windward Side?
Juliana’s Hotel offers the perk of free parking.
Can I book refundable hotels in Windward Side?
If you’re looking for the flexibility to change your plans to Windward Side, most properties offer refundable* bookable rates. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
Where can I stay with my pet in Windward Side?
Your furry friend can stay with you at this pet-friendly hotel: El Momo Cottages.
Which Windward Side hotels do travelers like for their great location?
Our guests love Scout’s Place Hotel for its great location.
Where can I stay in Windward Side if I'm looking for a reasonably priced accommodation?
Scout’s Place Hotel is an accommodation you might want to consider that’ll save you money.
Where can I stay if I'm traveling to Windward Side for a family-friendly vacation?
Your kids are welcome at Selera Dunia Boutique Hotel.
Where should I stay in Windward Side for a vacation with my partner?
El Momo Cottages is a good option for a romantic getaway with your special someone.
What will the weather in Windward Side be like during my visit?
Windward Side is a great place to visit any time of year with an average temperature of 78°F during the coldest months.
Why should I book my Windward Side hotel with Hotels.com?
There are lots of reasons to book your Windward Side trip with us: our free cancellations on selected hotels* gives you flexibility, our Price Guarantee ensures you always get the lowest price, and you can earn reward nights with our Rewards Program saving your money.