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30 Dec - 31 Dec
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31 Dec - 1 Jan
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2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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Our top choices for Windward Side hotels

Outdoor pool
Saba Arawak Hotel

Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.4 out of 10, Very good, (75)
This business-friendly hotel in Windward Side offers free WiFi and convenient parking. Cool off in the outdoor pool and savour Caribbean dishes at Liam's Cuisine restaurant. Dutch Museum of Saba and Saba Heritage Centre are just moments away.
"Room was clean, great friendly staff especially Ahmad who welcomes everyone with big smile and is very helpful "
United States
shahzad
Saba Arawak Hotel
Superior Studio Suite, Patio, Mountain View
The Scenery Hotel Saba

The Scenery Hotel Saba

The Scenery Hotel Saba
2.0 star property
Windward Side
The price is NZ$1,733
includes taxes & fees
13 Jan - 14 Jan 2026
The Scenery Hotel Saba
Outdoor pool, pool loungers
El Momo Cottages

El Momo Cottages

El Momo Cottages
3.0 star property
Windward Side
8.6 out of 10, Excellent, (55)
Nestled in Windward Side, this guesthouse offers a refreshing outdoor pool and on-site dining. Explore the nearby Dutch Museum and Saba Heritage Centre, then unwind on the scenic terrace amid lush gardens.
"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."
Canada
Georgina
The price is NZ$255
includes taxes & fees
25 Jan - 26 Jan 2026
El Momo Cottages
Outdoor pool
Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (22)
Just minutes from F.D. Roosevelt Airport, this boutique hotel offers an outdoor pool and garden terrace. Enjoy free breakfast, WiFi, and parking while exploring nearby Government Guesthouse and Dutch Reformed Church attractions.
"It was great time to stay with comfortable "
American Samoa
YONG
Quill Gardens Boutique Hotel
Premium Bungalow, Non Smoking | Living area
Talk of the Town Inn & Suites

Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
9.0 out of 10, Wonderful, (12)
Discover this welcoming hotel with a sparkling outdoor pool in Oranjestad, just minutes from Government Guesthouse and Dutch Reformed Church. Enjoy free WiFi, parking, and relax in the lush garden and terrace.
"pleasant & enjoyable, clean."
United States
Donovan
The price is NZ$228
includes taxes & fees
31 Dec - 1 Jan 2026
Talk of the Town Inn & Suites
Reception
The Old Gin House

The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.2 out of 10, Very good, (54)
Seaside serenity meets historic elegance at this Oranjestad retreat. Enjoy free breakfast while overlooking the bay, then cool off in the outdoor pool. With Fort Oranje and Lower Town Beach nearby, plus a restaurant and garden, this colonial gem offers the perfect Caribbean escape.
"Staff was friendly. The property and surroundings were beautiful full of old Caribbean charm"
United States
James
The price is NZ$304
includes taxes & fees
4 Jan - 5 Jan 2026
The Old Gin House
View from property
Barrel House St. Eustatius

Barrel House St. Eustatius

Barrel House St. Eustatius
3.0 star property
Oranjestad
8.0 out of 10, Very good, (1)
Enjoy a beachfront stay at this B&B featuring 2 restaurants and a welcoming bar/lounge. Located near Lower Town Beach and Fort Oranje, this retreat offers free WiFi and parking just 2 minutes from Roosevelt Airport.
"Ce n’est pas un hĂŽtel, comme indiquĂ© sur ExpĂ©dia : pas de rĂ©ception, pas de piscine, mais une simple maison. La propriĂ©taire a « manquĂ© notre rĂ©servation » : donc logement pas prĂ©parĂ© Ă  notre arrivĂ©e. Puis elle parle de vĂ©rifier si nous avons rĂ©servĂ© la formule avec petit dĂ©jeuner, alors qu’Expedia affiche que le petit dĂ©jeuner est compris
 A noter aussi que la terrasse devant la maison ( cĂŽtĂ© mer) est celle du restaurant voisin."
France
Valérie
Barrel House St. Eustatius
Front of property
Palm Spring Inn

Palm Spring Inn

Palm Spring Inn
3.0 star property
Oranjestad
8.6 out of 10, Excellent, (14)
Located just minutes from Government Guesthouse, this cosy inn offers apartments with fully equipped kitchens and private balconies. Free WiFi and parking add convenience while the garden provides a peaceful retreat after exploring nearby Dutch Reformed Church.
"Great place lovely staff"
United States
Dameon
The price is NZ$219
includes taxes & fees
30 Jan - 31 Jan 2026
Palm Spring Inn
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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Stay near popular Windward Side attractions

Dutch Museum of Saba

You can spend time studying the exhibits at Dutch Museum of Saba during your travels in Windward Side. While you're in the area, wander around the gardens.
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Saba Heritage Center

You can spend an afternoon browsing the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area.
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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
The beautiful island of Saba
Photo by Stills 'n' stories
Open Photo by Stills 'n' stories

Top Windward Side Hotel Reviews

Saba Arawak Hotel

Saba Arawak Hotel

10/10 Excellent
"Room was clean, great friendly staff especially Ahmad who welcomes everyone with big smile and is very helpful "
shahzad 1-night trip
Posted 2 weeks ago
Saba Arawak Hotel

More cheap accommodation in Windward Side

Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool

Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool

Oranjestad
Get rates

Frequently asked questions

Where is the best place for a stay in Windward Side?
El Momo Cottages is ranked highly by Expedia customers. This guest house offers a restaurant and an outdoor pool. Another top choice for your visit based on reviews is Saba Arawak 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?
Home a way from home in the Unspoiled queen of the Caribbean.: This highly rated holiday home rental in Windward Side is located in the city centre, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden. 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. El Momo Cottages and Flamboyant Cottage - Spectacular View & Pool are a couple of other choices that feature an on-site pool. View all hotels with pools in Windward Side.
What is the best spa hotel in Windward Side?
The Scenery Hotel Saba is a top spa hotel with 30 rooms, free WiFi and laundry facilities. Treat yourself to a massage at the on-site spa. See all spa hotels 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 8 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 Dutch Museum of Saba, Saba Heritage Center 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.