A calm sea with a mountain in the distance.

Windward Side Castle Hotels

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Windward Side

A hotel with a balcony, a view of a hill, and a clear sky.

1. Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.2 out of 10, Very good, (109 reviews)
"Love the place"
United States
EMAD
$151 nightly
The price is $159
Nov 9 - Nov 10
Total with taxes and fees
Saba Arawak Hotel
A cluster of houses with red roofs, surrounded by dense greenery and trees.

2. El Momo Cottages

El Momo Cottages
3.0 star property
Windward Side
8.6 out of 10, Excellent, (63 reviews)
"Unique place overviewing the hills of Saba. Not a high class place to stay (in accordance with the rates), but everything is just good! Charming place, good service, good amenities, wonderful staff. I had a joyful stay and a great time!"
United States
Christina
$133 nightly
The price is $140
Nov 14 - Nov 15
Total with taxes and fees
El Momo Cottages
A row of hotel rooms with red roofs, a wooden deck, and a view of the sea.

3. Scenery Hotel Saba

Scenery Hotel Saba
3.5 star property
Windward Side
$314 nightly
The price is $330
Nov 9 - Nov 10
Total with taxes and fees
Scenery Hotel Saba
A pool with lounge chairs and a stone patio, surrounded by lush greenery and overlooking a hilly landscape.

4. 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
10.0 out of 10, Exceptional, (4 reviews)
"The house was amazing we will be back again… Thank you Michael!"
United States
Tim L.
$423 nightly
The price is $423
Dec 1 - Dec 2
Total with taxes and fees
Home a way from home in the Unspoiled queen of the Caribbean.
A cozy room with a high ceiling, large windows, a sofa, two wicker chairs, and a wooden table.

5. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
8.2 out of 10, Very good, (20 reviews)
"Great location, nice people, clean."
Netherlands
Nadine
$98 nightly
The price is $104
Dec 9 - Dec 10
Total with taxes and fees
Talk of the Town Inn & Suites
A two-story building with a balcony, surrounded by lush tropical plants and a sign for 'The Old Sun House Restaurant Bar'.

6. The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.4 out of 10, Very good, (65 reviews)
"Helpful, friendly staff. Included breakfast was tasty. Wine at sunset was nice. Enjoyed the stay very much."
United States
Regan
$159 nightly
The price is $170
Nov 21 - Nov 22
Total with taxes and fees
The Old Gin House
A paved pathway flanked by palm trees and buildings with a clear sky above.

7. Palm Spring Inn

Palm Spring Inn
3.0 star property
Oranjestad
8.2 out of 10, Very good, (16 reviews)
"Great place lovely staff"
United States
Dameon
$150 nightly
The price is $160
Nov 18 - Nov 19
Total with taxes and fees
Palm Spring Inn
A large, two-story house with a swimming pool, surrounded by lush greenery and a mountain in the background.

8. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (32 reviews)
"Great stay. Everything was superb."
United States
Donald
$165 nightly
The price is $176
Dec 4 - Dec 5
Total with taxes and fees
Quill Gardens Boutique Hotel
A brick pathway leading to a white building with a stone facade and a door.

9. Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad

Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Oranjestad
7.0 out of 10, Good, (2 reviews)
"The appartment is spacious and has everything you need. It was very neat and clean and the host Davon fast in response. The location is a quiet neighbourhood, not far away from the center. Thanks for having us. "
Netherlands
sytske m.
$169 nightly
The price is $175
Nov 19 - Nov 20
Total with taxes and fees
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
An outdoor patio with a table and chairs, a wicker sofa, and a view of the ocean.

10. Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views

Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
Sint Eustatius
8.0 out of 10, Very good, (1 review)
$201 nightly
The price is $212
Nov 9 - Nov 10
Total with taxes and fees
Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windward Side Hotel Reviews

El Momo Cottages

El Momo Cottages

10/10 Excellent
"Fun little place to stay at Saba. Not a traditional hotel, but each room is in it's own little cabin basically in a jungle with a patio and a bathroom. The jungle gets surprisingly loud at night and the morning views from our cabin were stunning. There is a lot of stairs everywhere around the property, so you'll have to be comfortable carrying your luggage and climbing the stairs up and down. Swimming pool was a very nice touch after a long day of hiking."
Martina 2-night trip
Posted 1 month ago
El Momo Cottages

Find out more about Windward Side

Windward Side Castles information

Number of reviews
137
Accommodation
0 Castles
Lowest Price
$104
Highest Price
$423