Title: Book The Best Hotels in Windward Side for 2026 from CA $176 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Windward Side](https://expedia.ca/Windward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals)[Things to do in Windward Side](https://expedia.ca/Things-To-Do-In-Windward-Side.d11638.Travel-Guide-Activities)[Windward Side Car Rentals](https://expedia.ca/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide)[Windward Side Vacation Packages](https://expedia.ca/Windward-Side.d11638.Destination-Travel-Guides) ![View from room at Juliana’s hotel. Super affordable and great views close to restaurants.](https://images.trvl-media.com/place/11638/c1211919-9bcc-466a-acbd-26fb5183377a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Meghan Watters # Find hotels in Windward Side from CA $176 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windward Side hotels ![Outdoor pool](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d8a26561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saba Arawak Hotel [](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information) Windward Side 8.4/10 Very good (73) "The hotel is very clean" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Yvonne Traveling for leisure CA $177 CA $208 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/499a6edb.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/86000000/85540000/85534600/85534552/56795a50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quill Gardens Boutique Hotel [](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information) Oranjestad 9.6/10 Exceptional (22) "It was great time to stay with comfortable " ![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg) YONG [](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information) ![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) ![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) ![Front of property](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f0544aaf.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) ### The Old Gin House [](https://www.expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information) Oranjestad 8.2/10 Very good (54) "Staff was friendly. The property and surroundings were beautiful full of old Caribbean charm" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $248 CA $265 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.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) ![Premium Bungalow, Non Smoking](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/f86bd64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Bungalow, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/1153cce4.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) ### Talk of the Town Inn & Suites [](https://www.expedia.ca/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information) Oranjestad 9.0/10 Wonderful (12) "pleasant & enjoyable, clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donovan CA $170 CA $183 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/1d1cb7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/4c62066a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/288f1499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchenette](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/2c07626c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm Spring Inn [](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information) Oranjestad 8.6/10 Excellent (14) "Great place lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dameon CA $158 CA $176 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.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](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/ca77f211.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 | Terrace/patio](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/6e9f669e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Barrel House St. Eustatius [](https://www.expedia.ca/Oranjestad-Hotels-Barrel-House-St-Eustatius.h85535622.Hotel-Information) Oranjestad 8.0/10 Very good (1) "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 [](https://www.expedia.ca/Oranjestad-Hotels-Barrel-House-St-Eustatius.h85535622.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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-29&endDate=2025-12-30®ionId=11638&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindward-Side-Hotels.d11638.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindward-Side-Hotels.d11638.Travel-Guide-Hotels) ## Learn more about Windward Side Colourful cottages with red roofs dot this charming village where hikers begin their ascent of Mount Scenery. Grab a meal at Scout's Place after exploring the Saba Conservation Foundation's trail network that winds through cloud forests. [See all hotels in Windward Side](https://www.expedia.ca/Hotel-Search?startDate=2025-12-29&endDate=2025-12-30&adults=2®ionId=11638) ![The beautiful island of Saba](https://images.trvl-media.com/place/11638/bec9a351-370d-430b-b191-7beddd830e10.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) Photo by Stills 'n' stories ## More cheap stays in Windward Side ![Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool](https://images.trvl-media.com/lodging/122000000/121310000/121302100/121302035/76b27700_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool Oranjestad [Get rates](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=121302035&PinnedHotelID=121302035&HadPinnedHotel=true®ionId=11638) [](https://expedia.ca/Oranjestad-Hotels-Welcome-To-Casa-Sabean.h121302035.Hotel-Information) ## Find out more about Windward Side ### Top reasons to visit Windward Side - **Stunning Scenery:** Windward Side features breathtaking views of the Windward Shores and Windward Coast, perfect for relaxation. - **Rich Cultural Experiences:** Immerse yourself in the local history and vibrant culture through museums and art galleries. - **Outdoor Adventures:** Ideal for outdoor enthusiasts, offering numerous activities amidst beautiful landscapes. - **Diverse Accommodation:** Enjoy a range of comfortable stays, from 3 to 3.5-star hotels to charming guesthouses. - **Romantic Atmosphere:** Experience the enchanting vibe of the area, especially around the scenic Windward Passage. ### Find great hotels in Windward Side In Windward Side, you'll discover a variety of comfortable hotel accommodations ranging from 3 to 3.5 stars, including both hotels and guesthouses. Whether you're seeking a business-friendly environment, an adventurous getaway, or pet-friendly options, this charming destination has something for everyone. Explore the hospitality of Windward Islands with numerous choices that cater to your vacation needs, making your stay both enjoyable and memorable. - **[Saba Arawak Hotel:](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)** Nestled in the heart of Windward Side, Saba Arawak Hotel offers a unique blend of adventure and business amenities, making it an ideal choice for both thrill-seekers and corporate travellers. This 3-star establishment features a variety of adventure sports activities, including nearby hiking, cave exploring, sailing, fishing, and snorkeling. Guests can unwind in comfortable accommodations while enjoying the convenience of business services offered on-site. The hotel's commitment to providing an adventurous yet professional atmosphere makes it a standout choice for diverse vacationers. - **[El Momo Cottages:](https://www.expedia.ca/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information)** For those seeking a more homey retreat, El Momo Cottages presents a charming guesthouse experience in Windward Side. This property is particularly welcoming to pet owners, as it allows pets on-site with a free pet policy. The inviting atmosphere and pet-friendly amenities ensure that you and your furry companions can enjoy a relaxing stay. With its quaint design and community feel, El Momo Cottages is perfect for travellers who appreciate nature and wish to explore the beautiful surroundings of Saba with their pets. - **[The Cottage Club Hotel:](https://www.expedia.ca/Windward-Side-Hotels-The-Cottage-Club-Hotel.h44546768.Hotel-Information)** Offering a touch of luxury with its 3.5-star rating, The Cottage Club Hotel is an excellent choice for those seeking both comfort and entertainment. Situated in Windward Side, this hotel features modern amenities such as digital television for guests to enjoy. Visitors can relish the scenic views of the village and partake in various nearby activities. The Cottage Club Hotel seamlessly combines a cozy atmosphere with engaging entertainment options, making it a delightful base for exploring the wonders of Saba. ### Where to stay in Windward Side Windward Side, nestled in the picturesque Saba, offers an unforgettable vacation experience perfect for beach lovers and outdoor enthusiasts. Explore the stunning Windward Shores and the breathtaking Windward Coast, where relaxation and scenic views abound. Just a stone's throw away from the vibrant Windward Passage, visitors can immerse themselves in the area's rich history and romantic atmosphere. Whether seeking luxury or tranquility, Windward Side and its surrounding gems promise a memorable getaway. - **[Oranjestad:](https://www.expedia.ca/Oranjestad-Hotels.d11643.Travel-Guide-Hotels)** Located 30.6km from Windward Side, Oranjestad is a vibrant city that offers a delightful mix of outdoor activities and stunning beach scenery. This popular destination sees a seasonal influx of visitors, particularly from November to January. In Oranjestad, you can enjoy golf at local courses, relax at resorts, and explore nearby attractions like the history museum and picturesque beaches. The city's bay serves as a beautiful backdrop for various water sports, making it a perfect spot for both adventure and relaxation. - **[The Bottom:](https://www.expedia.ca/The-Bottom-Hotels.d6140251.Travel-Guide-Hotels)** Just 1.6km away from Windward Side, The Bottom is a charming city that immerses visitors in local culture and outdoor experiences. It attracts travellers especially in January, April, and September. Here, you can partake in hiking adventures and enjoy golfing amidst breathtaking landscapes. The Bottom is home to a rich history, showcased in its museums, while its beaches and nearby mountains offer stunning vistas for nature enthusiasts. This city is a wonderful place to experience the heart of Saba's island life. - **[Upper Zion's Hill:](https://www.expedia.ca/Upper-Zions-Hill-Hotels.d553248635975871741.Travel-Guide-Hotels)** Nestled within the area of Windward Side, Upper Zion's Hill is a quaint village known for its beautiful beaches, including a nudist beach that attracts those seeking a unique sunbathing experience. The village sees a moderate number of visitors throughout the year, with peaks in the winter months. Upper Zion's Hill is ideal for those looking to unwind by the sea and enjoy a more laid-back atmosphere while still being close to the vibrant activities of Windward Side. The tranquil charm of this village is perfect for relaxation and beach enjoyment. ### Things to do in Windward Side Windward Side is an ideal destination for beach lovers and outdoor enthusiasts, offering stunning scenery and a range of activities. Visitors can enjoy hiking through scenic trails, diving, and scuba diving in crystal-clear waters. It's also a popular spot for windsurfing and day trips to explore the beautiful surroundings. This charming location promises a memorable vacation experience for all adventure seekers. ### Booking tips and Expedia advantages for Windward Side When visiting Windward Side, you can save money by taking advantage of free activities like Well's Bay Beach. The best time to visit for lower prices is from May to June and October, while booking your hotel about a month in advance can secure better deals. Look for last-minute offers on Expedia, especially on Mondays, the cheapest day to stay. Consider bundling your hotel, flights, and activities for added savings. Use Expedia’s tools to filter by budget and eco-friendly options for sustainable stays, ensuring you find great deals on accommodations. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Windward Side are May to June and October, where the prices are slightly lower. This is in comparison to February and November to December, where prices are slightly higher. - **The best time to book a hotel:** Book your hotel in Windward Side about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Windward Side is Monday. The most expensive day to stay in Windward Side is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your results by price, starting with the most affordable hotels, allowing you to easily find the best deals. Additionally, you have the option to narrow down your choices by hotel type; for instance, selecting the "Eco-certified" filter will highlight sustainable and environmentally-friendly accommodations that you can book. - **Consider bundling your trip:** You can save money by combining your Windward Side hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in Windward Side Windward Side offers a fantastic vacation experience for beach lovers and outdoor enthusiasts alike, showcasing stunning scenery and rich culture. Explore local attractions such as history museums, mountains, and art galleries that cater to adventurers seeking unique experiences. Whether you're interested in the vibrant local culture or the breathtaking landscapes of the Windward Islands, you're sure to find plenty of activities to enjoy during your stay. - **Dutch Museum of Saba:** Immerse yourself in the rich history and culture of Saba at the Dutch Museum. This local gem showcases artifacts and exhibits that reflect the island's unique heritage, making it a perfect stop for culture enthusiasts. - **Mt Scenery:** Experience adventure and breathtaking views at Mt Scenery, located a mere 1.1km from Windward Side. The hike to the summit offers stunning panoramas and a chance to connect with nature, ideal for outdoor lovers. - **Jo Bean Glass Art Studio:** Visit Jo Bean Glass Art Studio to witness the intricate craftsmanship of glass art. This gallery not only exhibits stunning pieces but also provides insight into the artistic process, enriching your cultural experience. ### Best time to go to Windward Side The best time to visit Windward Side can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windward Side falls in September, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Windward Side falls in March, visitor numbers are high and weather is mostly sunny with no rain. | **![calendar icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly cloudy icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation rate icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------- | --------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------ | ------------------------------------------------------------------------------------------------------------------ | | January | 78.4°F (25.8°C) | No Rain (Dry) | Mostly Sunny | Average | Average | | February | 77.9°F (25.5°C) | No Rain (Dry) | Mostly Sunny | Average | Slightly High | | March | 77.7°F (25.4°C) | No Rain (Dry) | Mostly Sunny | High | Average | | April | 78.8°F (26.0°C) | No Rain (Dry) | Mostly Sunny | High | Average | | May | 80.2°F (26.8°C) | Light Rain | Mostly Cloudy | High | Slightly Low | | June | 81.5°F (27.5°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | July | 82.0°F (27.8°C) | Light Rain | Mostly Sunny | Average | Average | | August | 82.6°F (28.1°C) | Light Rain | Mostly Sunny | Average | Average | | September | 82.9°F (28.3°C) | Light Rain | Mostly Sunny | Average | Average | | October | 82.6°F (28.1°C) | Light Rain | Mostly Cloudy | Low | Slightly Low | | November | 81.3°F (27.4°C) | Light Rain | Mostly Cloudy | Low | Slightly High | | December | 79.7°F (26.5°C) | Light Rain | Mostly Sunny | Low | Slightly High | ### The nearest major airports for your trip to Windward Side To reach Windward Side, you can fly into Saba's Juancho E. Yrausquin Airport ([SAB](https://www.expedia.ca/Juancho-E-Yrausquin-Airport-Hotels.0-aSAB-0.Travel-Guide-Filter-Hotels)), located 1.6km away. Nearby hotel options include the 3.5-star Cottage Club Hotel and the 3-star [Saba Arawak Hotel](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information), both 1.6km from the airport. Alternatively, you can fly into F.D. Roosevelt Airport (EUX) in Oranjestad, 30.6km away. Recommended accommodations include the 4-star [Golden Rock Dive And Nature Resort](https://www.expedia.ca/Oranjestad-Hotels-Oasis-Golden-Rock-Dive-Nature-Resort.h64649184.Hotel-Information), 3.2km from the airport, and the 4-star[ Quill Gardens Boutique Hotel](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information), 1.3km away. Many hotels offer convenient transportation services to and from both airports, ensuring a smooth travel experience. ## Recent reviews of Windward Side hotels ![The Old Gin House](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/e4b10408_y.jpg) ### The Old Gin House 5/5 Excellent "Staff was friendly. The property and surroundings were beautiful full of old Caribbean charm" A verified traveller stayed at The Old Gin House Posted 4 days ago [](https://expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.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 5/5 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" A verified traveller stayed at Talk of the Town Inn & Suites Posted 7 days ago [](https://expedia.ca/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 3/5 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." A verified traveller stayed at Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad Posted 2 weeks ago [](https://expedia.ca/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 5/5 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!" A verified traveller stayed at El Momo Cottages Posted 3 weeks ago [](https://expedia.ca/Windward-Side-Hotels-El-Momo-Cottages.h11944556.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! 5/5 Excellent "Our host and the atmosphere in and around the cottage " A verified traveller stayed at Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away! Posted 1 month ago [](https://expedia.ca/Windward-Side-Hotels-Historic-Saban-Cottage-In-Windwardside.h78382857.Hotel-Information) ![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/738de9aa_y.jpg) ### Saba Arawak Hotel 5/5 Excellent "It was an amazing experience " A verified traveller stayed at Saba Arawak Hotel Posted 3 months ago [](https://expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.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! 5/5 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?" A verified traveller stayed at Peter Hytte is close to everything at great price! Posted 4 months ago [](https://expedia.ca/Windward-Side-Hotels-Peter-Hytte-Is-Close-To-Everything-At-Great-Price.h89687379.Hotel-Information) ![ Quill Gardens Boutique Hotel](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/c6c425a2_y.jpg) ### Quill Gardens Boutique Hotel 5/5 Excellent I like this location "It was great time to stay with comfortable " A verified traveller stayed at Quill Gardens Boutique Hotel Posted 5 months ago [](https://expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information) ![Home a way from home in the Unspoiled queen of the Caribbean.](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234367/65f31ece_y.jpg) ### Home a way from home in the Unspoiled queen of the Caribbean. 5/5 Excellent Fantastic property & hosts "Iris House is cute, comfortable, great/walkable location and with everything we needed for a great stay. Owner and manager both very helpful - highly recommend." A verified traveller from Tucson, AZ stayed at Home a way from home in the Unspoiled queen of the Caribbean. Posted 6 months ago [](https://expedia.ca/Windward-Side-Hotels-Home-A-Way-From-Home-In-The-Unspoiled-Queen-Of-The-Caribbean.h73234367.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Windward Side that travellers recommend? ### What are the best budget hotels in Windward Side? ### When is the best time to go to Windward Side? > The peak season, which stretches from March to May, attracts a vibrant mix of tourists eager to explore the region's breathtaking landscapes and enjoy its rich cultural offerings. This is an excellent time for those who appreciate outdoor activities, as the crystal-clear waters and lush surroundings invite you to partake in hiking, snorkelling, or simply wandering through charming local villages. > > > For families and couples alike, the combination of warm weather and lively events during April makes it an ideal period for creating lasting memories. The local festivals often showcase traditional music and cuisine, allowing you to immerse yourself in the unique culture of Windward Side. Furthermore, the extended daylight hours mean you can make the most of your days, whether you're exploring stunning viewpoints or indulging in the local culinary scene. > > > If you're looking for a more budget-friendly experience, consider October. This month offers a quieter atmosphere, allowing you to enjoy the natural beauty and attractions without the crowds, all at a lower price point. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Windward Side hotel booking with Expedia? ### How much is the nightly rate at a Windward Side hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Adults Only Resorts & in Saba ](https://www.expedia.ca/Destinations-In-Saba-Adults-Only-Resorts.0-0-d11753-tAdultsOnlyResorts.Hotel-Filter-Destinations) - [All Inclusive Resorts and in Saba ](https://www.expedia.ca/Destinations-In-Saba-All-Inclusive-Hotel.0-0-d11753-tAllInclusiveHotel.Hotel-Filter-Destinations) - [Beach Hotel Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Beach-Hotel.0-0-d11753-tBeachHotel.Hotel-Filter-Destinations) - [Boutique Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Boutique-Hotel.0-0-d11753-tBoutiqueHotel.Hotel-Filter-Destinations) - [Casino Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Casino-Hotel.0-0-d11753-tCasinoHotel.Hotel-Filter-Destinations) - [Family Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Family-Hotel.0-0-d11753-tFamilyHotel.Hotel-Filter-Destinations) - [Golf Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Golf-Hotel.0-0-d11753-tGolfHotel.Hotel-Filter-Destinations) - [Green Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Green-Sustainable.0-0-d11753-tGreenSustainable.Hotel-Filter-Destinations) - [Honeymoon Resorts and in Saba ](https://www.expedia.ca/Destinations-In-Saba-Honeymoon-Hotels.0-0-d11753-tHoneymoonHotels.Hotel-Filter-Destinations) - [Hotels with a Pool in Saba ](https://www.expedia.ca/Destinations-In-Saba-Hotel-With-Pool.0-0-d11753-tHotelwithPool.Hotel-Filter-Destinations) - [Hotels with smoking rooms in Saba ](https://www.expedia.ca/Destinations-In-Saba-Hotels-With-Smoking-Rooms.0-0-d11753-tHotelswithsmokingrooms.Hotel-Filter-Destinations) - [Hotels with Tennis Courts in Saba ](https://www.expedia.ca/Destinations-In-Saba-Hotels-With-Tennis-Courts.0-0-d11753-tHotelswithTennisCourts.Hotel-Filter-Destinations) - [Lgbt Friendly Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-LGBT-Friendly-Hotel.0-0-d11753-tLGBTFriendlyHotel.Hotel-Filter-Destinations) - [Luxury Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Luxury-Hotel.0-0-d11753-tLuxuryHotel.Hotel-Filter-Destinations) - [Romantic Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Romantic-Hotel.0-0-d11753-tRomanticHotel.Hotel-Filter-Destinations) - [Shopping Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Shopping-Hotel.0-0-d11753-tShoppingHotel.Hotel-Filter-Destinations) - [Ski Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Ski-Hotel.0-0-d11753-tSkiHotel.Hotel-Filter-Destinations) - [Spa Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Spa-Hotel.0-0-d11753-tSpaHotel.Hotel-Filter-Destinations) - [Hotel Wedding Venues Hotels in Saba ](https://www.expedia.ca/Destinations-In-Saba-Wedding-Hotels.0-0-d11753-tWeddingHotels.Hotel-Filter-Destinations) - [Saba Hotels ](https://www.expedia.ca/Destinations-In-Saba.d11753.Hotel-Destinations) - [Hell's Gate Hotels ](https://www.expedia.ca/Hells-Gate-Hotels.d11639.Travel-Guide-Hotels) - [Hotels near Juancho E. 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