Title: Best Cottages in Windward Side in 2026 | Expedia.co.uk

[Windward Side Travel Guide](https://expedia.co.uk/Windward-Side.dx11638)[Hotels in Windward Side](https://expedia.co.uk/Windward-Side-Hotels.d11638.Travel-Guide-Hotels)[Holiday Rentals in Windward Side](https://expedia.co.uk/Windward-Side-Holiday-Rentals.d11638.Travel-Guide-HolidayRentals)[Windward Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windward-Side.d11638.Car-Hire-Guide)[Windward Side Holidays](https://expedia.co.uk/Windward-Side.d11638.Holidays-City-Breaks)

![The beautiful island of Saba](https://images.trvl-media.com/place/11638/bec9a351-370d-430b-b191-7beddd830e10.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Stills 'n' stories

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## Check prices for these dates

In two weeks

[20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=11638&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=11638&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=11638&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=11638&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Windward Side

![Front of property](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/44320344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; Caribbean cuisine, pool views ](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/2e08764f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/121cb9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Saba Arawak Hotel

[](https://www.expedia.co.uk/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

Windward Side

8.4/10

Very good

(79 reviews)

"Friendly Staff "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Trilochan

[](https://www.expedia.co.uk/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

![Superior Cottage, 2 Single Beds, Kitchenette, Ocean View | View from room](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/59c43c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/fa3ed7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Cottage, 2 Single Beds, Kitchenette, Ocean View | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/6af124d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/4f3bf157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### El Momo Cottages

[](https://www.expedia.co.uk/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information)

Windward Side

8.6/10

Excellent

(55 reviews)

"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Georgina

£89

includes taxes & fees

14 Feb - 15 Feb

[](https://www.expedia.co.uk/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/5cea60f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/13552485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, scuba diving](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f062af63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/e4b10408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Old Gin House

[](https://www.expedia.co.uk/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

Oranjestad

8.4/10

Very good

(56 reviews)

"Very awesome hotel, great history and staff was excellent, great job."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael

£149

includes taxes & fees

17 Feb - 18 Feb

[](https://www.expedia.co.uk/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/a30f8ce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/e2cedb25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/7f149889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/499a6edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Quill Gardens Boutique Hotel

[](https://www.expedia.co.uk/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

Oranjestad

9.6/10

Exceptional

(25 reviews)

"It was great time to stay with comfortable "

![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg)

YONG

[](https://www.expedia.co.uk/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

![Premium Bungalow, Non Smoking | Living area](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/ecfb3641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/c48f0519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Bungalow, Non Smoking | Private kitchen | Espresso maker](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/1153cce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/638aa03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Talk of the Town Inn & Suites

[](https://www.expedia.co.uk/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information)

Oranjestad

9.2/10

Wonderful

(13 reviews)

"Great location, nice people, clean."

![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg)

Nadine

£98

includes taxes & fees

20 Feb - 21 Feb

[](https://www.expedia.co.uk/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/23cae97a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/416dcc8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/d5b575ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/4e0d4adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information)

Oranjestad

6.0/10

(1 review)

"The staff was ok but they came late to open for me. While the property was generally up to standards there was not toilet tissue neither bathing soap. Did not.know i had to provide these myself."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

WINSLEY

£121

includes taxes & fees

14 Feb - 15 Feb

[](https://www.expedia.co.uk/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/ed6c9c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment | Living area | 40-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/7b2b7164.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/26c7ebbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment | Living area | 40-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/ca77f211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Barrel House St. Eustatius

[](https://www.expedia.co.uk/Oranjestad-Hotels-Barrel-House-St-Eustatius.h85535622.Hotel-Information)

Oranjestad

8.0/10

Very good

(1 review)

"Ce n’est pas un hôtel, comme indiqué sur Expédia : pas de réception, pas de piscine, mais une simple maison. La propriétaire a « manqué notre réservation » : donc logement pas préparé à notre arrivée. Puis elle parle de vérifier si nous avons réservé la formule avec petit déjeuner, alors qu’Expedia affiche que le petit déjeuner est compris… A noter aussi que la terrasse devant la maison ( côté mer) est celle du restaurant voisin."

![France](https://a.travel-assets.com/egds/marks/flags/fr.svg)

Valérie

£181

includes taxes & fees

10 Mar - 11 Mar

[](https://www.expedia.co.uk/Oranjestad-Hotels-Barrel-House-St-Eustatius.h85535622.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/112b37fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/f1a67479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/268182e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/c0dd92a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Oranjestad-Hotels-Spacious-2-Bedroom-Apartment-In-Sint-Eustatius-With-Beautiful-Sunset-Views.h125407386.Hotel-Information)

Sint Eustatius

£147

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Oranjestad-Hotels-Spacious-2-Bedroom-Apartment-In-Sint-Eustatius-With-Beautiful-Sunset-Views.h125407386.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/c6a9a19c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/9e2c7c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/8a35946a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/1b2b92a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad

[](https://www.expedia.co.uk/Oranjestad-Hotels-Chic-1-Bedroom-Apartment-With-AC.h112808442.Hotel-Information)

Oranjestad

£121

includes taxes & fees

14 Feb - 15 Feb

[](https://www.expedia.co.uk/Oranjestad-Hotels-Chic-1-Bedroom-Apartment-With-AC.h112808442.Hotel-Information)

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.

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Cottages

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## Top Windward Side Hotel Reviews

![ Quill Gardens Boutique Hotel](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/c6c425a2_y.jpg)

###  Quill Gardens Boutique Hotel

10/10 Excellent

"Great space and wonderful staff "

[](https://expedia.co.uk/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

![Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/a524e520_y.jpg)

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

10/10 Excellent

"My husband and I enjoyed a wonderful stay in this comfortable, well situated and historic cottage. Our host, Jeff, was extraordinary, providing an excellent orientation to beautiful Saba and informing us about everything we needed to know to maximize our brief time on the island. His referrals to restaurants and activities were perfect. We look forward to returning as soon as we can!"

[](https://expedia.co.uk/Windward-Side-Hotels-Historic-Saban-Cottage-In-Windwardside.h78382857.Hotel-Information)

![The Old Gin House](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/e4b10408_y.jpg)

### The Old Gin House

10/10 Excellent

"Very awesome hotel, great history and staff was excellent, great job."

[](https://expedia.co.uk/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/738de9aa_y.jpg)

### Saba Arawak Hotel

10/10 Excellent

"Friendly Staff "

[](https://expedia.co.uk/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

![Flamboyant Cottage - Spectacular View & Pool](https://images.trvl-media.com/lodging/35000000/34010000/34006200/34006194/3c3130af_y.jpg)

### Flamboyant Cottage - Spectacular View & Pool

10/10 Excellent

"Lovely cabin with incredible view. "

[](https://expedia.co.uk/Windward-Side-Hotels-Beautiful-Gingerbread-Cottage-Spectacular-View-Pool.h34006194.Hotel-Information)

![Talk of the Town Inn & Suites](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/ecfb3641_y.jpg)

### Talk of the Town Inn & Suites

10/10 Excellent

"The Talk of the Town is a stunning nice, cosy hotel with a small compound of summer houses and swimming pool. Most exciting and many thanks! Raymond"

[](https://expedia.co.uk/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information)

![Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/2a7adee1_y.jpg)

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

6/10 Okay

"The staff was ok but they came late to open for me. While the property was generally up to standards there was not toilet tissue neither bathing soap. Did not.know i had to provide these myself."

[](https://expedia.co.uk/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information)

![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg)

### El Momo Cottages

10/10 Excellent

"The staff is fantastic! Cabins are simple, clean and comfortable. Breakfast was delicious.The views are amazing! Be prepared to climb to enjoy the views. Lots of stairs but worth it!"

[](https://expedia.co.uk/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information)

![Peter Hytte is close to everything at great price!](https://images.trvl-media.com/lodging/90000000/89690000/89687400/89687379/465c91ea_y.jpg)

### Peter Hytte is close to everything at great price!

10/10 Excellent

"It's safe to say I could absolutely live here!!! This cottage is in the heart! Jeffery is amazing. He's helpful, laid back and kind LIKE EVERYONE here! I'm booking again soon. Where else can you sleep with all your doors and windows open in nature and be safe?"

[](https://expedia.co.uk/Windward-Side-Hotels-Peter-Hytte-Is-Close-To-Everything-At-Great-Price.h89687379.Hotel-Information)

## Find out more about Windward Side

## Windward Side Cottages information

| Number of reviews | 228        |
| ----------------- | ---------- |
| Accommodation     | 3 Cottages |
| Lowest Price      | £89        |
| Highest Price     | £181       |