Book Cheap Hotels in Windward Side

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Tonight
Check prices in Windward Side for tonight, Nov 15 - Nov 16
Nov 15 - Nov 16
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Nov 16 - Nov 17
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Nov 21 - Nov 23

Most frequently booked Windward Side hotels

Saba Arawak Hotel

Saba Arawak Hotel

3 out of 5
The peak, Windward Side, Saba
Free cancellation
Reserve now, pay when you stay
0.17 km from city centre
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Stay at this 3-star business-friendly hotel in Windward Side. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Dutch Museum of Saba and Saba Heritage Center are located nearby.
Pool
Parking included
El Momo Cottages

El Momo Cottages

3 out of 5
Booby Hill, Windward Side, Saba
0.53 km from city centre
The price is CA $160 per night
CA $160
CA $171 total
Nov 23 - Nov 24
includes taxes & fees
Stay at this 3-star guesthouse in Windward Side. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Dutch Museum of Saba and Saba Heritage Center are located nearby.
Pool
Pet-friendly
Flamboyant Cottage - Spectacular View & Pool

Flamboyant Cottage - Spectacular View & Pool

0.76 km from city centre
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Stay at this cottage in Windward Side. Enjoy free WiFi, private pools, and a garden. Popular attractions Dutch Museum of Saba and Saba Heritage Center are located nearby.
Pool
Kitchen
Spyglass is a Private Villa With 360 View Near Windwardside.

Spyglass is a Private Villa With 360 View Near Windwardside.

0.08 km from city centre
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Stay at this villa in Windward Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Saba Heritage Center and Dutch Museum of Saba are located nearby.
Hot tub
Kitchen
The Cottage Club Hotel

The Cottage Club Hotel

3.5 out of 5
17a Grey Bush Street, Windward Side, Saba
0.07 km from city centre
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Stay at this 3.5-star hotel in Windward Side. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art Studio are located nearby.
Pool
Parking included
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!

0.17 km from city centre
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Stay at this cottage in Windward Side. Enjoy free WiFi, a garden, and patios. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art Studio are located nearby.
Kitchen
Free WiFi
Peter Hytte is close to everything at great price!

Peter Hytte is close to everything at great price!

0.16 km from city centre
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Stay at this cottage in Windward Side. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art Studio are located nearby.
Kitchen
Pet-friendly
Home a way from home in the Unspoiled queen of the Caribbean.

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

0.8 km from city centre
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Stay at this vacation home in Windward Side. Enjoy free WiFi, private pools, and a garden. Popular attractions Mt Scenery and Harry L Johnson Museum are located nearby.
Pool
Kitchen
The Old Gin House

The Old Gin House

3 out of 5
Oranjebaai 1, Oranjestad, Sint Eustatius
Free cancellation
Reserve now, pay when you stay
30.55 km from city centre
The price is CA $252 per night
CA $252
CA $270 total
Nov 18 - Nov 19
includes taxes & fees
Stay at this 3-star beach hotel in Oranjestad. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Oranje and Lower Town Beach are located nearby.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Windward Side
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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 hotels essential information

Accommodation
25 hotels
Lowest Price
CA $171
Highest Price
CA $270
Popular hotels
Saba Arawak Hotel, El Momo Cottages, Flamboyant Cottage - Spectacular View & Pool, Spyglass is a Private Villa With 360 View Near Windwardside., The Cottage Club Hotel, Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!, Peter Hytte is close to everything at great price!, Home a way from home in the Unspoiled queen of the Caribbean., The Old Gin House

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 CA $171 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

The Old Gin House

The Old Gin House

5 out of 5
Posted 6 days ago
Travelocity Verified Review
"Spacious room with a fabulous view. Friendly staff, convenient location. "
A verified traveller stayed at The Old Gin House
The Old Gin House

Areas of Windward Side