A calm sea with a mountain in the distance.

Windward Side Hotels from S$141

  • 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
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Filter by

Star rating

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
EMAD
S$203
includes taxes & fees
13 Oct - 14 Oct
Saba Arawak Hotel
A bedroom with a bed, bedside tables, a bench, a wall-mounted air conditioner, a framed picture, and a floor lamp.
A balcony with a view of the ocean and greenery.
A modern living room with a sofa, armchair, and a round coffee table.
The exterior of the Scenery Hotel with a prominent sign, large windows, and two potted plants in front.

2. Scenery Hotel Saba

Scenery Hotel Saba
Windward Side
S$507
includes taxes & fees
3 Oct - 4 Oct
Scenery Hotel Saba
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.

3. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
Oranjestad
United Kingdom
ARIEH
S$141
includes taxes & fees
2 Oct - 3 Oct
Talk of the Town Inn & Suites
A beach with palm trees, a stone wall, and a building in the background.
A room with a brick wall, wooden floor, a brown leather sofa, and two large arched windows with a view of greenery.
A two-story building with a balcony, surrounded by lush tropical plants and a sign for 'The Old Sun House Restaurant Bar'.
A room with a rustic brick wall, a wooden ceiling, and a large brass vase with red flowers on a stone base.

4. The Old Gin House

The Old Gin House
Oranjestad
United States
Regan
S$230
includes taxes & fees
1 Nov - 2 Nov
The Old Gin House
A pathway lined with palm trees and tropical plants, leading to a building with a blue facade.
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.
A hallway with tiled flooring, large vases with flowers, and a painting on the wall.

5. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
Oranjestad
United States
Reginaldo
S$225
includes taxes & fees
2 Oct - 3 Oct
Quill Gardens Boutique Hotel
A table set for dining with a view of the sea at sunset, a metal pot, and several wine glasses.
A brick building with a red roof, a gated entrance, and a parked vehicle in the background.
A rocky beach with a clear blue sky and calm sea.
A spacious living room with a high wooden ceiling, a chandelier, and a staircase leading to an upper level.

6. Barrel House St. Eustatius

Barrel House St. Eustatius
Oranjestad
France
Valérie
S$268
includes taxes & fees
3 Oct - 4 Oct
Barrel House St. Eustatius
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 hotel room with a bed, a wicker basket with toiletries, a painting of a palm leaf, and a lamp.
A corridor with a door, a chair, and a railing with plants.

7. Palm Spring Inn

Palm Spring Inn
Oranjestad
United Kingdom
lucy
S$204
includes taxes & fees
4 Oct - 5 Oct
Palm Spring Inn
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

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 2 months 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 2 months 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 4 months ago
Talk of the Town Inn & Suites

Frequently asked questions

Where is the best place for a stay in Windward Side?
Based on our traveller data, Saba Arawak Hotel is one of the top choices for your stay. This hotel offers a restaurant and an outdoor pool. Other good options for your visit include El Momo Cottages and Scenery Hotel Saba. See all available top hotels, or 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 Scenery Hotel Saba 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 12 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, Harry L Johnson Museum and Saba Heritage Center. 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.

Explore a world of travel with Expedia