Photo by Meghan Watters

Beach Hotels & Resorts in Windward Side from NZ$182

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Best Windward Side Beach Hotels

El Momo Cottages
Outdoor pool, pool loungers

El Momo Cottages

3.0 star property
8.6 out of 10, Excellent, (47)
"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "
The price is NZ$182
includes taxes & fees
1 Dec - 2 Dec
El Momo Cottages
Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (64)
"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local...
Spyglass is a Private Villa With 360 View Near Windwardside.
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Aerial view

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

10.0 out of 10, Exceptional, (8)
"Three of us came to Saba for the first time, for a diving vacation. We had a great time and Althea's Cottage worked out perfectly for us. The 2 bedrooms with bath were at opposite ends of the house, we had a kitchen with dining, a large living room sitting area and back yard patio area. We were able to use an outdoor clothesline daily for drying our diving attire. The cottage is located with convenient walking access several restaurants, 2 grocery stores, a delicious bakery. and the Swinging...
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Poets and Painters Cottage
Terrace/patio

Poets and Painters Cottage

The price is NZ$703
includes taxes & fees
25 Nov - 26 Nov
Poets and Painters Cottage
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.
Don't see what you're looking for?
See all available properties in Windward Side
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

What is Windward Side like for travellers who love the beach?
Find a great place to stay in Windward Side, which has a lot to offer the traveller looking to book a beach holiday.
What's the best hotel to stay near the beach in Windward Side?
Scout’s Place Hotel is a top hotel with free continental breakfast and free WiFi, and it’s located close to Cove Bay Beach . Other good choices to stay near the beach include Juliana’s Hotel and El Momo Cottages.
How many beach hotels are there in Windward Side?
Expedia has 8 beach hotels in Windward Side that are great for your beachside getaway.
When's the best time for a beach holiday in Windward Side?
Plan your trip to the beach with a look at year-round temperatures 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.
What is there to see and do around Windward Side?
After arriving and checking into your hotel, you’ll probably want to explore your surroundings. If you’re eager to check out the beaches, head to Cove Bay Beach or Well’s Bay Beach for some relaxation by the water. Make time for a range of local attractions, which include Dutch Museum of Saba and Saba Heritage Center. For additional things to see and do, consider a visit to Mt Scenery or Harry L Johnson Museum.
What's the best way to get to my beach hotel in Windward Side?
Here’s some information to help you get to and around your beach accommodation in Windward Side with ease. The closest major airport is in Saba (SAB-Juancho E. Yrausquin), located 1.3 mi (2.1 km) from the city centre. If you’d like to venture out around the area, you may want to rent a car for your trip.