Photo by Stills 'n' stories

Search Windward Side hotels

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Sept - 3 Sept
Tomorrow
3 Sept - 4 Sept
This weekend
5 Sept - 7 Sept
Next weekend
12 Sept - 14 Sept

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Windward Side

Saba Arawak Hotel
Outdoor pool

Saba Arawak Hotel

3.0 star property
8.4 out of 10, Very good, (66)
"The staffs where very helpful and answers questions respectfully."
Saba Arawak Hotel
Palm Spring Inn
Front of property

Palm Spring Inn

3.0 star property
8.6 out of 10, Excellent, (14)
"Great place lovely staff"
The price is AU$195
includes taxes & fees
18 Sept - 19 Sept
Palm Spring Inn
Quill Gardens Boutique Hotel
Outdoor pool

Quill Gardens Boutique Hotel

4.0 star property
9.6 out of 10, Exceptional, (21)
"Lovely place and surroundings, big room, good service"
Quill Gardens Boutique Hotel
The Old Gin House
Hiking

The Old Gin House

3.0 star property
8.2 out of 10, Very good, (51)
"hotel is close to town, at the ocean/beach, walkable and had good access to some nice options for lunch and diner, at hotel and nearby"
The price is AU$304
includes taxes & fees
5 Sept - 6 Sept
The Old Gin House
Talk of the Town Inn & Suites
Premium Bungalow, Non Smoking | Living area

Talk of the Town Inn & Suites

3.0 star property
9.0 out of 10, Wonderful, (10)
"Great location, nice people, clean."
The price is AU$155
includes taxes & fees
3 Sept - 4 Sept
Talk of the Town Inn & Suites
Barrel House St. Eustatius
View from property

Barrel House St. Eustatius

3.0 star property
8.0 out of 10, Very good, (1)
"Ce n’est pas un hôtel, comme indiqué sur Expédia : pas de réception, pas de piscine, mais une simple maison. La propriétaire a « manqué notre réservation » : donc logement pas préparé à notre arrivée. Puis elle parle de vérifier si nous avons réservé la formule avec petit déjeuner, alors qu’Expedia affiche que le petit déjeuner est compris… A noter aussi que la terrasse devant la maison ( côté mer) est celle du restaurant voisin."
Barrel House St. Eustatius
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Windward Side

Colourful cottages with red roofs dot this charming village where hikers begin their ascent of Mount Scenery. Grab a meal at Scout's Place after exploring the Saba Conservation Foundation's trail network that winds through cloud forests.

See all hotels in Windward Side
Photo by Meghan Watters
Open Photo by Meghan Watters

Top Windward Side Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Where is the best place for a stay in Windward Side?

Based on our traveller data, Saba Arawak Hotel is one of the top choices for your stay. This hotel offers a restaurant and an outdoor pool. Other good options for your visit include El Momo Cottages and The Cottage Club Hotel. See all available top hotels, or vacation rentals in Windward Side.

What are some of the best holiday rentals that Windward Side has to offer?

Beautiful Traditional Saba Cottage With all the Modern Amenities: This highly rated holiday home rental in Windward Side is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly. Another good choice for your trip to Windward Side is Home a way from home in the Unspoiled queen of the Caribbean.. See all vacation rentals in Windward Side.

If I need to cancel my hotel reservation in Windward Side, will I receive a refund?

Yes, most hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Windward Side.

What's the best dog-friendly place to stay in Windward Side?

El Momo Cottages is a top guest house for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Windward Side.

What are some hotels with pools in Windward Side?

Saba Arawak Hotel: Features complimentary high-speed (wired) Internet access, an outdoor pool and free self parking. Another option that features an on-site pool is El Momo Cottages. View all hotels with pools in Windward Side.

How is it to stay in Windward Side?

Visitors can enjoy all that Windward Side has to offer, including the seaside and mountain views. This city also attracts tourists with its scenic landscape. In Windward Side, there are 12 hotels and other accommodation options to choose from. Find out more about Windward Side.

What should I do while I'm visiting Windward Side?

Cultural venues include Saba Heritage Center, Dutch Museum of Saba and Harry L Johnson Museum. A couple of additional sights to add to your itinerary are Mt Scenery and Jo Bean Glass Art Studio. Take a look at what more there is to see and do in Expedia's Windward Side guide.

What's the seasonal weather in Windward Side?

The hottest months are usually September and October, with an average temperature of 28°C, while the coldest months are February and March, with an average of 26°C. Average annual precipitation for Windward Side is 921 mm.