Hotels in Windward Side
Search over 24 hotels from $128
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Top Rated Windward Side Hotels
Saba Arawak Hotel
The peak Windward Side Saba
Free Cancellation
Reserve now, pay when you stay
0.1 mi from city center
Guests of Saba Arawak Hotel enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. If you plan to drive, free parking is available. Front-desk staff can help with luggage storage, and provide local restaurant recommendations.
Pool
Parking included
El Momo Cottages
Booby Hill Windward Side Saba
0.33 mi from city center
$139 nightly
The price is $146 total per night
$146 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
Guests of El Momo Cottages enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. A stay here includes free offsite parking. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include laundry facilities and a garden.
Pool
Pet friendly
Flamboyant Cottage - Spectacular View & Pool
Windward Side Saba
0.47 mi from city center
At this cottage, guests have access to an outdoor pool and a garden.
Pool
Kitchen
Spyglass is a Private Villa With 360 View Near Windwardside.
windwardside Saba
0.05 mi from city center
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.
Hot Tub
Kitchen
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Windward Side Saba
0.1 mi from city center
At this cottage, guests have access to a garden.
Kitchen
Free WiFi
The Cottage Club Hotel
17a Grey Bush Street Windward Side Saba
0.04 mi from city center
An outdoor pool, coffee in a common area, and a terrace are featured at The Cottage Club Hotel. If you plan to drive, free parking is available. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include laundry facilities and a garden.
Pool
Parking included
Peter Hytte is close to everything at great price!
Windward Side Saba
0.1 mi from city center
At this cottage, guests have access to a garden.
Kitchen
Pet friendly
Home a way from home in the Unspoiled queen of the Caribbean.
Saba Caribbean Netherlands
0.49 mi from city center
Guests staying at this vacation home can enjoy an outdoor pool, barbecue grills, and a garden.
Pool
Kitchen
The Old Gin House
Oranjebaai 1 Oranjestad Sint Eustatius
Free Cancellation
Reserve now, pay when you stay
18.97 mi from city center
$180 nightly
The price is $193 total per night
$193 total
Dec 29 - Dec 30
Total with taxes and fees
Guests of The Old Gin House enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. If you drive, put free parking to good use. Front-desk staff can assist with luggage storage and securing valuables. Other amenities at this beach hotel include laundry facilities and a garden.
Pool
Breakfast included
Quill Gardens Boutique Hotel
Road to English Quarter Oranjestad Sint Eustatius
Free Cancellation
Reserve now, pay when you stay
19.77 mi from city center
Guests of Quill Gardens Boutique Hotel enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. If you decide to drive, there's free parking. A multilingual staff is on hand to assist with tours/tickets and luggage storage. Other amenities at this adults-only guesthouse include laundry facilities, a garden, and a communal living room.
Pool
Breakfast included
Talk of the Town Inn & Suites
L.E. Saddler Road #9 Oranjestad St. Eustatius
18.97 mi from city center
$124 nightly
The price is $133 total per night
$133 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Talk of the Town Inn & Suites enjoy features like an outdoor pool, free WiFi in public areas, and express check-in. If you drive, put free parking to good use. Front-desk staff can assist with securing valuables and dry cleaning/laundry. Additional amenities include express check-out, a terrace, and laundry facilities.
Pool
Parking included
Palm Spring Inn
Erick R Gibbs Road 2 Oranjestad
19.32 mi from city center
$120 nightly
The price is $128 total per night
$128 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
Guests staying at Palm Spring Inn enjoy free WiFi in public areas, laundry facilities, and a garden. If you plan to drive, free parking is available. Staff members are on hand to provide tour or ticket assistance and luggage storage. This apartment building also has barbecue grills.
Kitchen
Pet friendly
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.
Where should you stay in Windward Side?
What are the best hotels to stay with pets in Windward Side?
El Momo Cottages is a pet-friendly guesthouse with free WiFi, private patios, and a terrace.
What are some favorite hotels in downtown Windward Side?
These are some of the most popular hotels in downtown Windward Side:
- Saba Arawak Hotel is a hotel offering free WiFi, free parking, and in-room kitchenettes.
- El Momo Cottages is a guesthouse offering free WiFi, private patios, and a terrace.
- The Cottage Club Hotel is a hotel offering free WiFi, free parking, and in-room kitchenettes.
Sights to visit in the heart of Windward Side include Dutch Museum of Saba, Cove Bay Beach and Well's Bay Beach.
What are the best hotels to stay near Harry L Johnson Museum?
Harry L Johnson Museum should be toward the top of your to-do list while you're visiting Windward Side. This collection of historical artifacts is 0.3 miles from the center and attracts travelers from all over. Squeeze the most out of your visit by basing yourself nearby at Selera Dunia Boutique Hotel, just 0.1 miles away. Other top-rated hotels include Scout's Place Hotel, located 0.1 miles away, and Spyglass is a Private Villa With 360 View Near Windwardside, which is 0.1 miles away. You'll be able to jump out of bed and get to this attraction in no time!
Windward Side hotels essential information
Accommodation | 24 hotels |
|---|---|
Lowest Price | $128 |
Highest Price | $193 |
Popular hotels | Saba Arawak Hotel, El Momo Cottages, Flamboyant Cottage - Spectacular View & Pool, Spyglass is a Private Villa With 360 View Near Windwardside., Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!, The Cottage Club Hotel, 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, Quill Gardens Boutique Hotel, Talk of the Town Inn & Suites, Palm Spring Inn |
Recent Reviews
Saba Arawak Hotel
5/5 Excellent
"Room was clean, great friendly staff especially Ahmad who welcomes everyone with big smile and is very helpful "
A verified traveler stayed at Saba Arawak Hotel
Posted 12 days ago
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