Hotels in Windward Side

October 2026
7
November 2026

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Check prices for these dates

This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Where to stay in Windward Side?

1. Saba Arawak Hotel

Saba Arawak Hotel
Windward Side
$135
$159 total
includes taxes & fees
Oct 8 - Oct 9
Saba Arawak Hotel

2. Scenery Hotel Saba

Scenery Hotel Saba
Windward Side
$315
$365 total
includes taxes & fees
Nov 4 - Nov 5
Scenery Hotel Saba

3. The Old Gin House

The Old Gin House
Oranjestad
$177
$189 total
includes taxes & fees
Oct 8 - Oct 9
The Old Gin House

4. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
Oranjestad
$165
$176 total
includes taxes & fees
Oct 9 - Oct 10
Quill Gardens Boutique Hotel

5. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
Oranjestad
$103
$110 total
includes taxes & fees
Oct 8 - Oct 9
Talk of the Town Inn & Suites

6. Palm Spring Inn

Palm Spring Inn
Oranjestad
$144
$160 total
includes taxes & fees
Oct 8 - Oct 9
Palm Spring Inn
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Go beyond your typical stay in Windward Side

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Our prices for hotels in Windward Side are cheapest in November

Price trends for hotels in Windward Side

Pricing is based on two traveler single night rates
View properties in October

October

High 29°C / low 27°C. Cloudy most days.
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Monthly weather averages (˚C)

Top landmarks in Windward Side

Dutch Museum of Saba

8.4/10 (5 reviews)
The center of Windward Side is home to cultural attractions like Dutch Museum of Saba, so you might want to stop by during your stay. If you want to experience more of the culture Windward Side has to offer, head to Mt Scenery, Cove Bay Beach, and Well's Bay Beach.
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Saba Heritage Center

The center of Windward Side is home to cultural attractions like Saba Heritage Center, so you might want to stop by during your stay. If you want to experience more of the culture Windward Side has to offer, head to Dutch Museum of Saba, Mt Scenery, and Cove Bay Beach.
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Harry L Johnson Museum

8.8/10 (3 reviews)
The center of Windward Side is home to cultural attractions like Harry L Johnson Museum, so you might want to stop by during your stay. If you want to experience more of the culture Windward Side has to offer, head to Dutch Museum of Saba, Mt Scenery, and Cove Bay Beach.
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Jo Bean Glass Art Studio

9.8/10 (8 reviews)
If museums are on your list of things to see, then you might want to head to Jo Bean Glass Art Studio, located in the heart of Windward Side.If you want to see more of the museums in Windward Side, you can easily walk to Dutch Museum of Saba or Saba Heritage Center.
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Learn more about Windward Side

Windward Side is applauded for its cultural attractions such as Dutch Museum of Saba and Harry L Johnson Museum. The city has something for everyone including sights like Mt Scenery and Saba Heritage Center within a scenic setting.

See all hotels in Windward Side
A lush green mountain with a white picket fence and buildings with red roofs.

Check out reviews of Windward Side hotels guests love

Saba Arawak Hotel

Saba Arawak Hotel
Windward Side

10/10 Exceptional

United States
shahzad
Saba Arawak Hotel

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
Oranjestad

10/10 Exceptional

United States
Donald
Quill Gardens Boutique Hotel

The Old Gin House

The Old Gin House
Oranjestad

10/10 Exceptional

United States
JRC
The Old Gin House

Palm Spring Inn

Palm Spring Inn
Oranjestad

10/10 Exceptional

United States
Anonymous traveler
Palm Spring Inn

Frequently Asked Questions

What accommodations do travelers recommend in Windward Side?

Where can I find free parking with my stay in Windward Side?

El Momo Cottages offers the perk of free parking.

Can I book refundable hotels in Windward Side?

If you're looking for the flexibility to change your plans to Windward Side, most properties offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Windward Side if I'm looking for a reasonably priced accommodation?

The Scenery Hotel Saba is an accommodation you might want to consider that'll save you money.

What will the weather in Windward Side be like during my visit?

Windward Side is a great place to visit any time of year with an average temperature of 78°F during the coldest months.

Why should I book my Windward Side hotel with Hotels.com?

There are lots of reasons to book your Windward Side trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.