A calm sea with a mountain in the distance.

Search Windward Side hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
6 Sept - 7 Sept
Tomorrow
7 Sept - 8 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Filter by

Property class

Guest rating

Our top choices for Windward Side hotels

A rectangular swimming pool with a white tiled deck, surrounded by white railings and lounge chairs.
A hotel with multiple balconies, outdoor seating, and a view of the sea.
A hotel with a balcony, a view of a hill, and a clear sky.
A buffet table with various food items and a selection of wine bottles.

1. Saba Arawak Hotel

Saba Arawak Hotel
Windward Side
United States
Jose
AU$184
includes taxes & fees
7 Sept - 8 Sept
Saba Arawak Hotel
A rooftop terrace with two lounge chairs under a large umbrella, surrounded by potted plants and a wooden fence.
A modern bedroom with a bed, desk, chair, and a flat-screen TV.
A modern living room with a sofa, armchair, and a round coffee table.
A modern interior with a high ceiling, a sofa, ottomans, and potted plants.

2. Scenery Hotel Saba

Scenery Hotel Saba
Windward Side
AU$476
includes taxes & fees
7 Sept - 8 Sept
Scenery Hotel Saba
A beach with palm trees, a stone wall, and a building in the background.
A brick building with a balcony, green shutters, and a garden with various plants.
A room with a rustic brick wall, a wooden ceiling, and a large brass vase with red flowers on a stone base.
A two-story building with a balcony, surrounded by lush tropical plants and a sign for 'The Old Sun House Restaurant Bar'.

3. The Old Gin House

The Old Gin House
Oranjestad
United States
Regan
AU$245
includes taxes & fees
7 Oct - 8 Oct
The Old Gin House
A cozy room with a high ceiling, large windows, a sofa, two wicker chairs, and a wooden table.
A swimming pool with lounge chairs, a wooden deck, and a building with a red roof.
A compact kitchen with a bar area, two bar stools, a refrigerator, and a microwave.
A bedroom with a large bed, a window with a view, a painting on the wall, and a wooden door.

4. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
Oranjestad
United States
José Miguel
AU$165
includes taxes & fees
7 Sept - 8 Sept
Talk of the Town Inn & Suites
A pathway lined with palm trees and tropical plants, leading to a building with a blue facade.
A clear blue pool with a wooden deck, white railings, and a view of the ocean and mountains in the background.
A large, two-story house with a swimming pool, surrounded by lush greenery and a mountain in the background.
A breakfast table set with plates, cutlery, a vase of flowers, and a view of the ocean.

5. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
Oranjestad
United States
Reginaldo
AU$245
includes taxes & fees
9 Sept - 10 Sept
Quill Gardens Boutique Hotel
A paved pathway flanked by palm trees and buildings with a clear sky above.
A kitchen with a counter, a chair, and a wall with a motivational quote.
A corridor with a door, a chair, and a railing with plants.
A living room with a sofa, a coffee table, a TV, and shelves with plants.

6. Palm Spring Inn

Palm Spring Inn
Oranjestad
United Kingdom
lucy
AU$222
includes taxes & fees
7 Sept - 8 Sept
Palm Spring Inn
A table set for dining with a view of the sea at sunset, a metal pot, and several wine glasses.
A spacious living room with a high wooden ceiling, a chandelier, and a staircase leading to an upper level.
A brick building with a red roof, a gated entrance, and a parked vehicle in the background.
A spacious living room with a white sofa, a wooden ceiling, a TV mounted on the wall, and a large painting.

7. Barrel House St. Eustatius

Barrel House St. Eustatius
Oranjestad
France
Valérie
AU$337
includes taxes & fees
14 Sept - 15 Sept
Barrel House St. Eustatius
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Windward Side attractions

Dutch Museum of Saba

8.4/10 (5 reviews)
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.
See properties

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.
See properties

Harry L Johnson Museum

8.8/10 (3 reviews)
You can spend an afternoon exploring the galleries in Harry L Johnson Museum in Windward Side. While you're in the area, wander around the gardens.
See properties

Jo Bean Glass Art Studio

9.8/10 (8 reviews)
You can spend an afternoon browsing the exhibits at Jo Bean Glass Art Studio during your trip to Windward Side. While you're in the area, wander around the gardens.
See properties

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
A mountainous landscape with a body of water in the foreground.
Photo by Stills 'n' stories

Top Windward Side Hotel Reviews

Recent Reviews in Windward Side

Saba Arawak Hotel

Saba Arawak Hotel

10/10 Excellent
"Love the place"
EMAD 2-night trip
Posted 23 hours ago
Saba Arawak Hotel
El Momo Cottages

El Momo Cottages

10/10 Excellent
"El Momo Cottage is a simple basic place you will love, if you just want to take a break and go back to basic. The wooden cabin located in hill with an awesome view. I return home fully rested and recharged. Just by staying there. Definitely I'm going back. It's my retraer in the unspoiled queen called Saba"
Wendell 5-night trip
Posted 3 weeks ago
El Momo Cottages
Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel

10/10 Excellent
"Anton was an excellent host. Best chef in town."
Reginaldo 3-night trip
Posted 3 weeks ago
Quill Gardens Boutique Hotel
Talk of the Town Inn & Suites

Talk of the Town Inn & Suites

8/10 Good
"The room was nice, clean spacious but did not have a TV . Nice kitchen.The location is good , near the airport"
ARIEH 2-night trip
Posted 3 months ago
Talk of the Town Inn & Suites
Flamboyant Cottage - Spectacular View & Pool

Flamboyant Cottage - Spectacular View & Pool

10/10 Excellent
"My husband and I had a great stay at Flamboyant Cottage. Before we arrived, the property manager had arranged for a taxi for us for both arrival and departure. The property manager met us at the cottage and took us grocery shopping right away, which made it very easy for us to choose between cooking or going out all week long. The cottage was nicely laid out with several different spaces to relax in: pool, gazebo, and porch. We had a great time hiking various trails on the island. Every meal we ate out, whether in Windwardside or The Bottom, was delicious. We met many nice people. Overall, we found Saba to be a very unique, beautiful, and safe place to visit!"
Jennifer K. 6-night trip
Posted 4 months ago
Flamboyant Cottage - Spectacular View & Pool
Spyglass is a Private Villa With 360 View Near Windwardside.

Spyglass is a Private Villa With 360 View Near Windwardside.

10/10 Excellent
"Absolutely gorgeous property. There are not many places you can go and get the view you get here. The house itself is very special - the pictures almost do not do it justice. The host is very responsive, and his staff is incredibly helpful in assisting you during your time on Saba. We ran into a snag with our departing flight, and Mark did everything in his power to assist us in getting home.Highly recommend staying here!"
Michael S. 3-night trip
Posted 4 months ago
Spyglass is a Private Villa With 360 View Near Windwardside.
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!

10/10 Excellent
"We’ve been to Saba/Althea cottage twice now … it’s one of our favorite spots in the world! "
Lydia M. 2-night trip
Posted 5 months ago
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Beautiful Traditional Saba Cottage With all the Modern Amenities

Beautiful Traditional Saba Cottage With all the Modern Amenities

10/10 Excellent
"Everything went well. The property was ready when we arrived. We do rent a car while on island, and parking was a bit hard to come by at times, but such is life there. There is a washer and dryer, and the shower had plenty of hot water. Overall it was in a great location, we walked to breakfast and dinner most nights. Also, it was a very quiet stay."
Andrea F. 8-night trip
Posted 9 months ago
Beautiful Traditional Saba Cottage With all the Modern Amenities

Frequently asked questions

What is the best area to stay in Windward Side?
The best area to stay in Windward Side is within the village itself, particularly around the central square and main road.This charming village is the largest settlement on Saba and is known for its distinctive red-roofed cottages and narrow, winding streets. The main road, called "The Road," connects the various parts of the village, and the central square is a natural gathering point. You'll find a selection of shops, local eateries, and small hotels dotted throughout.Couples looking for a peaceful and romantic escape will find Windward Side ideal. The village offers beautiful views of the surrounding mountains and the Caribbean Sea. You can enjoy quiet strolls along the footpaths, dine at intimate restaurants, and easily access hiking trails that lead to various viewpoints and natural pools.For solo travellers seeking a relaxed and friendly environment, Windward Side provides a welcoming base. It's easy to meet locals and other travellers in the village's small bars and cafes.
What are the best hotels in Windward Side that travellers recommend?
For a highly recommended hotel in Windward Side, consider the Saba Arawak Hotel.This 3-star hotel, with a very good 8.4 rating, is praised by guests for its quiet and spacious rooms. Its convenient location is set among mountains and offers ocean views. The hotel features an outdoor pool and a poolside restaurant, and guests frequently mention the delicious breakfast. Free and secured self-parking is also available.
What are the most romantic hotels in Windward Side for couples?
For a romantic stay in Windward Side for couples, the Saba Arawak Hotel is an excellent choice.The 3-star Saba Arawak Hotel, with an 8.4 rating, offers a wonderful setting for couples. Guests frequently comment on the quiet and spacious rooms, and the convenient location is often praised. The friendly and helpful staff contribute to a pleasant stay. The hotel features a beautiful pool and offers a delicious breakfast. Many rooms include a furnished balcony and ocean views, great for enjoying the scenery. The hotel also provides free WiFi, a kitchen, and complimentary self-parking. It is conveniently located just 1.1 km from Mt Scenery, making it easy to explore the natural beauty of the area.
What hotels are near Saba (SAB-Juancho E. Yrausquin)?
For hotels near Saba (SAB-Juancho E. Yrausquin) airport, consider the Saba Arawak Hotel.The 3-star Saba Arawak Hotel, with an 8.4 rating, is located just 2.3 kilometres from the airport, offering great convenience for travellers. Guests frequently mention the quiet and spacious rooms, and the friendly and helpful staff. The hotel provides free WiFi, a kitchen in the accommodations, and free toiletries. Guests also appreciate the delicious breakfast and the beautiful pool.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windward Side.
How can I save on a hotel booking in Windward Side with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Windward Side hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Windward Side?
Prices for hotels in Windward Side often vary, but you can find a great deal from AU$165 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

Explore a world of travel with Expedia