Book The Best Hotels in Windward Side for 2024 from CA $138

Top 10 Windward Side hotels and places to stay

"Beautiful pool and nice view from balcony. Bed was okay. Breakfast at Liam's was good. Short walk into town. Good price for what you get. Nice to have kitchen if you want to cook."

CA $212 total

includes taxes & fees

Nov 26 - Nov 27

"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. "

CA $148 total

includes taxes & fees

Nov 28 - Nov 29

"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...

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

"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...

CA $573 total

includes taxes & fees

Nov 27 - Nov 28

"Beautiful views. Very centrally located and quiet. "

"Even though we had to pay for an unused night on account of a canceled ferry, this was a beautiful place in a gorgeous location close to everything in Windwardside. My kids and I enjoyed the private pool with a view."

"Our stay was fantastic! Cece was awesome and helpful in every way! She arranged a rental car for us at the house so we could get around the island independently. Views were magnificent and hacienda was perfect! Very clean with every amenity you could possibly want! Kitchen is fully stocked with anything you could possibly need to cook a meal. Don’t hesitate to book this magnificent home! You won’t be sorry!"

"The cottage is great, just as described. The beds are comfortable and clean. All of Windwardside is walking distance from this location, the grocery store is steps away. I would definitely stay here again."

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Hotels near Popular Windward Side Attractions

Find out more about Windward Side

Windward Side Travel Info

Number of hotels	29
Highest price	CA $503
Lowest price	CA $138
Known attractions	Well's Bay Beach, Cove Bay Beach and Dutch Museum of Saba
Hotels with nearby historical attractions	2
Hotels with free breakfast	2

Recent Reviews in Windward Side

5/5 Excellent

Fun and Eco Friendly

"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. "

A verified traveller stayed at El Momo Cottages

Posted 2 months ago

Beautiful Gingerbread Cottage - Spectacular View & Pool

5/5 Excellent

Unspoiled Queen of the Caribbean

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

A verified traveller stayed at Beautiful Gingerbread Cottage - Spectacular View & Pool

Posted 3 months ago

Spyglass is a Private Villa With 360 View Near Windwardside.

5/5 Excellent

Wonderful home. Amazing location.

"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 shops and restaurants are. We enjoyed the spectacular views of each sunrise and sunset with a good book in hand. We'll be back soon!"

A verified traveller stayed at Spyglass is a Private Villa With 360 View Near Windwardside.

Posted 6 months ago

5/5 Excellent

"The new owners are working hard to refresh this historic property. The seaside location is a gem and the staff members are friendly and attentive (special shout-out to Julia). The full breakfast is a wonderful benefit, and my mahi-mahi dinner was absolutely delicious! An added bonus is the proximity to another excellent restaurant, as well as a scuba center for those who come to Statia to dive. Thanks to Peter and Jeanette and your amazing staff!"

A verified traveller stayed at The Old Gin House

Posted 8 months ago

3/5 Okay

Serious revamp needed, last month.....

"Need to revamp, very overrun, it is a very beautiful property if run properly, or lat least cleaned and maintained properly. The pool and the pool area is a disaster, looks unhygienic, outdoor public area need a serious paint job, the tropical garden needs an gardener to prune and dead leaves all taken away, there are more mosquitoes than they should be. Could have been with an old world Caribbean charm , but not like this."

A verified traveller stayed at Queen’s Hotel Saba

Posted 1 year ago

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Other Hotels near Windward Side, Saba

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Frequently asked questions

Where is the best place for a stay in Windward Side?

El Momo Cottages is ranked highly by Expedia customers. This guesthouse offers a restaurant and an outdoor pool. Another top choice for your stay based on reviews is Saba Arawak Hotel. See all available top hotels, or vacation rentals in Windward Side.

What are some of the best vacation rentals in Windward Side?

Home a way from home in the Unspoiled queen of the Caribbean.: Visitors give good reviews to this Windward Side vacation home rental, which is located in the city center and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden. Some other top choices in Windward Side are Poets and Painters Cottage and Beautiful Traditional Saba Cottage With all the Modern Amenities. See all vacation rentals in Windward Side.

If I need to cancel my hotel reservation in Windward Side, will I receive a refund?

Yes, you'll find most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Windward Side.

Where can I learn more about changing or cancelling my trip to Windward Side?

For more information about rescheduling or cancelling your trip to Windward Side, go to https://www.expedia.com/service/.

What's the best hotel for a family trip to Windward Side?

El Momo Cottages is a guesthouse with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Find more child-friendly accommodations in Windward Side.

What's the best accommodation for a romantic vacation to Windward Side?

El Momo Cottages is a favorite guesthouse for couples, and features free WiFi and a garden. See all romantic hotels in Windward Side.

What's the best pet-friendly place to stay in Windward Side?

El Momo Cottages is a top guesthouse for people traveling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Windward Side.

What's the best hotel to stay near Dutch Museum of Saba?

Adjacent to Dutch Museum of Saba, Selera Dunia Boutique Hotel is one of the top choices for your stay based on our traveler data, and this 3-star B&B offers free breakfast and free parking. Other good options close by include El Momo Cottages and The Cottage Club Hotel.

What's the best hotel for a beach vacation 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 options to stay near the beach include Juliana's Hotel and El Momo Cottages. See more stays near the beach in Windward Side.

What's the best boutique hotel in Windward Side?

Selera Dunia Boutique Hotel is a favorite 3-star B&B with our travelers looking for a stylish accommodation, featuring 2 guestrooms, free breakfast, and free parking.

What are some hotels with pools in Windward Side?

Saba Arawak Hotel: Features complimentary wired internet access, an outdoor pool, and free self parking. Another option with an onsite pool is El Momo Cottages. View all hotels with pools in Windward Side.

What's the best place to stay near Juancho E. Yrausquin Airport (SAB)?

El Momo Cottages is a popular guesthouse, featuring a restaurant and an outdoor pool. It's located a short 1.4 mi (2.2 km) from Juancho E. Yrausquin Airport. Other options close to the airport are Selera Dunia Boutique Hotel and Scout's Place Hotel.

What's it like 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 15 hotels and other accommodations to choose from. Find out more about Windward Side.

What should I see while I'm in Windward Side?

Cultural venues include Dutch Museum of Saba, Saba Heritage Center, and Harry L Johnson Museum. A couple of additional sights to add to your agenda are Mt Scenery and Jo Bean Glass Art Studio. Check out what more to see and do in Expedia's Windward Side guide.

What's the seasonal weather like in Windward Side?

The hottest months are usually September and October with an average temp of 83°F, while the coldest months are February and March with an average of 78°F. Average annual precipitation for Windward Side is 36 inches.

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Top 10 Windward Side hotels and places to stay

Saba Arawak Hotel

El Momo Cottages

Spyglass is a Private Villa With 360 View Near Windwardside.

Flamboyant Cottage - Spectacular View & Pool

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

Poets and Painters Cottage

The Cottage Club Hotel

Peter Hytte is close to everything at great price!

Home a way from home in the Unspoiled queen of the Caribbean.

Your very own cottage

Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.

Beautiful Traditional Saba Cottage With all the Modern Amenities

Black Friday: Members save 30%+

Hotels near Popular Windward Side Attractions

Find out more about Windward Side

Windward Side Travel Info

Recent Reviews in Windward Side

El Momo Cottages

Beautiful Gingerbread Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

Saba Arawak Hotel

The Old Gin House

Talk of the Town

Queen’s Hotel Saba

Explore a world of travel with Expedia

Other Hotels near Windward Side, Saba

Explore more hotels

Frequently asked questions

Expedia's Latest Trends