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Top Windward Side hotels

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Windward Side
A garden is available at this cottage.
Great Little Community
The people of Saba are very friendly. This location has many fantastic restaurant choices within a short walk. Our host Jeffery was wonderful. Very helpful. Because he lives next door he's always available. The cottage was roomy for the 2 of us. WiFi worked great and there's plenty of electrical ...

Reviewed on Nov 27, 2024

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Opens in a new windowHistoric Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Peter Hytte is close to everything at great price!

Peter Hytte is close to everything at great price!

Windward Side
A garden is available at this cottage.
It's safe to say I could absolutely live here!!! This cottage is in the heart! Jeffery is amazing. He's helpful, laid back and kind LIKE EVERYONE here! I'm booking again soon. Where else can you sleep with all your doors and windows open in nature and be safe?

Reviewed on Sep 10, 2025

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Opens in a new windowPeter Hytte is close to everything at great price!
Home a way from home in the Unspoiled queen of the Caribbean.

Home a way from home in the Unspoiled queen of the Caribbean.

Saba
An outdoor pool is featured at this vacation home, along with a garden and barbecue grills.
Fantastic property & hosts
Iris House is cute, comfortable, great/walkable location and with everything we needed for a great stay. Owner and manager both very helpful - highly recommend.

Reviewed on Jul 9, 2025

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Opens in a new windowHome a way from home in the Unspoiled queen of the Caribbean.
Spyglass is a Private Villa With 360 View Near Windwardside.

Spyglass is a Private Villa With 360 View Near Windwardside.

windwardside
A hot tub is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
World Class experience
The villa is even more beautiful than the pictures. The views and gardens are even more vibrant and incredible than we expected. We were amazed at the incredible construction and attention to detail in the house. The building itself looks like much of the wood work and interior is custom built and ...

Reviewed on Mar 14, 2025

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Opens in a new windowSpyglass is a Private Villa With 360 View Near Windwardside.
Flamboyant Cottage - Spectacular View & Pool

Flamboyant Cottage - Spectacular View & Pool

Windward Side
An outdoor pool is featured at this cottage, along with a garden.
Spectacular
So lovely , whimsical, the view, the pool was so wonderful to cool off. Saba is magical.The cottage was clean and so many outdoor sitting spots.Could not recommend it more

Reviewed on Mar 18, 2025

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Opens in a new windowFlamboyant Cottage - Spectacular View & Pool
Saba Arawak Hotel

Saba Arawak Hotel

3 out of 5
The peak, Windward Side, Saba
Fully refundableReserve now, pay when you stay
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking ...
Room was cleaned everyday and the staff I met was very courteous. Thanks Saba Arawak Hotel

Reviewed on Oct 28, 2025

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Opens in a new windowSaba Arawak Hotel
El Momo Cottages

El Momo Cottages

3 out of 5
Booby Hill, Windward Side, Saba
$114 nightly
The price is $120 total per night from Nov 19 to Nov 20
$120 total
Nov 19 - Nov 20
Total with taxes and fees
A restaurant and an outdoor pool are featured at this guesthouse. WiFi in public areas is free. A terrace, a garden, and luggage storage are also on offer.
Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful.

Reviewed on Jul 20, 2025

Opens in a new windowEl Momo Cottages
The Old Gin House

The Old Gin House

3 out of 5
Oranjebaai 1, Oranjestad, Sint Eustatius
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $193 total per night from Nov 11 to Nov 12
$193 total
Nov 11 - Nov 12
Total with taxes and fees
This hotel features a restaurant and 2 bars/lounges. Enjoy the outdoor pool and free perks like cooked-to-order breakfast and free self parking. Free WiFi in ...
Beautiful location convenient to Scubaqua Dive Operation, a number of dining options, walking option to the town, fort, and views of the Caribbean!

Reviewed on Apr 12, 2025

Opens in a new windowThe Old Gin House
The Cottage Club Hotel

The Cottage Club Hotel

3.5 out of 5
17a Grey Bush Street, Windward Side, Saba
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. A terrace, a garden, and luggage storage are also on offer.
Beautiful views. Very centrally located and quiet.

Reviewed on Nov 24, 2021

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Opens in a new windowThe Cottage Club Hotel
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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.

Windward Side Hotel & Travel Guide\n

Are you intending on vacationing in Saba and hoping to reserve a place to sleep in or near Windward Side? You will discover 4 hotels on Travelocity within 6 miles (10 kilometers) of central Windward Side.

Are you trying to find a bed close to where the locals are? Read about the Scout's Place Hotel and El Momo Cottages that you can stay in within a 0.6 miles (1 kilometer) walk of central downtown.

The Queen’s Garden Resort & Spa as well as the Selera Dunia Boutique Hotel are two great accommodation options to explore. The Queen’s Garden Resort & Spa is positioned 1 mile (2 kilometers) from the center of Windward Side. The Selera Dunia Boutique Hotel is 0.4 miles (0.6 kilometers) away. As an alternative, you could look into the option of finding a room at the The Old Gin House. It can be found 19 miles (30 kilometers) away from the central area of Windward Side.

Travelocity's travel listing is an excellent way to learn the secrets of Windward Side.

Frequently asked questions

What are the top kid-friendly hotels in Windward Side?
Take some of the struggles out of traveling with young ones by booking a family-friendly Windward Side hotel. From well-thought-out amenities to innovative services, these stays offer perks that'll make your trip an effortless one: Your gang will enjoy staying at Selera Dunia Boutique Hotel. Complimentary breakfast and front desk services are a few of the things that help make this place a winner. Also check out The Cottage Club Hotel. It comes with a swimming pool, free WiFi and plenty of opportunities to spend time together.
Where can I find cheap hotels in Windward Side?
At Travelocity you'll find really nice hotels in Windward Side at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Windward Side rather than in Windward Side. We may find you even better rates, too.
How do I find the best Windward Side hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Windward Side then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Windward Side?
The cheapest hotel in Windward Side is $120. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Windward Side?
There are 25 hotels in Windward Side on Travelocity.
What are the best hotels in Windward Side?
Windward Side has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Windward Side for you!
When is the best time to visit Windward Side?
If you want the joy of a fun-filled trip in peak season, visit Windward Side during January, April and November. If you'd prefer the peace of off-season, book a stay during quieter months, such as May, June and September.
When is the cheapest time to stay in Windward Side?
Based on historic data is usually the cheapest month to visit Windward Side. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Windward Side?
There are multiple hotels in Windward Side that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Windward Side. We have plenty of kid-friendly hotels in Windward Side to choose from on Travelocity!
Why book a hotel in Windward Side through Travelocity?
Because we have the top hotels in Windward Side! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Windward Side on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Windward Side hotel reviews by fellow wanderers

Saba Arawak Hotel

Saba Arawak Hotel

5 out of 5
Posted 2 months ago
Travelocity Verified Review
"It was an amazing experience "
A verified traveler stayed at Saba Arawak Hotel
Saba Arawak Hotel

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