Find hotels in Windward Side from $107

Top reasons to visit Windward Side

• Stunning Scenery: Windward Side boasts breathtaking sea views and lush landscapes, perfect for relaxation and photography.
• Outdoor Adventures: Engage in hiking scenic trails, diving in vibrant waters, and enjoying various outdoor activities.
• Cultural Experiences: Explore historical museums, local galleries, and charming gingerbread cottages that reflect the island’s heritage.
• Golf Opportunities: Enjoy a day on the greens at the local golf course, catering to golf enthusiasts.
• Charming Accommodations: Choose from cozy hotels and bed & breakfasts that offer comfort and stunning views.

Find great hotels in and around Windward Side

Windward Side offers a delightful selection of accommodations, including charming hotels and cozy bed & breakfasts. Whether you're seeking a cottage hotel with stunning views, a pet-friendly option, or a place that caters to business travelers, you'll find the perfect stay here. Enjoy the laid-back atmosphere and make the most of your vacation in this beautiful destination, where comfort meets convenience.

• Saba Arawak Hotel: Embrace adventure at the 3-star Saba Arawak Hotel, boasting a guest rating of 8.4. Perfectly situated in Windward Side, this hotel caters to thrill-seekers and business travelers alike. The property offers an array of exciting activities, including nearby sailing, hiking, cave exploring, snorkeling, and fishing. Guests appreciate the blend of comfort and adventure, making it an ideal choice for those looking to explore the natural beauty of Saba while enjoying essential amenities.
• The Old Gin House: Just 19 miles from Windward Side, The Old Gin House invites guests to unwind in a beachside paradise, also rated at 8.4 stars. This charming 3-star hotel is perfect for those seeking a relaxing beach vacation. With direct access to the beach, visitors can soak up the sun and enjoy the soothing sounds of the ocean. Guests rave about the serene atmosphere and the delightful combination of coastal charm and modern conveniences, making it a great choice for beach lovers.
• El Momo Cottages: Discover the cozy and budget-friendly El Momo Cottages, which has a guest rating of 8.6. Situated in Windward Side, this guesthouse is perfect for pet owners looking for a welcoming retreat. With a pet-friendly policy that allows certain pets onsite, travelers can enjoy their vacation without leaving their furry friends behind. Guests appreciate the comfortable accommodations and the warm, inviting atmosphere that makes El Momo Cottages a beloved choice for a home away from home.

Where to stay near Windward Side

Windward Side offers an unforgettable Caribbean vacation experience, where stunning sea views and lush landscapes create a tranquil atmosphere. Explore the charming city center, indulge in luxury accommodations, and discover the island's rich history. With a perfect blend of relaxation and adventure, this picturesque destination invites travelers to enjoy both romantic sunsets and outdoor activities, making it an ideal spot for anyone seeking natural beauty and vibrant culture.

• Oranjestad: Situated 19 miles from Windward Side, Oranjestad is a vibrant city that offers a rich cultural experience along with stunning beach access. The travel experience here is moderately seasonal, with peak visitor numbers from November to January. Travelers flock to Oranjestad for its diverse activities, including snorkeling and diving in crystal-clear waters, as well as exploring local wildlife. Notable attractions include the history museum and beautiful beaches, including a nudist-friendly option, making it an ideal spot for both culture enthusiasts and beach lovers alike.
• The Bottom: Just 1 mile from Windward Side, The Bottom is a charming city known for its scenic beauty and outdoor adventures. The travel experience here is also moderately seasonal, with higher visitor numbers in January, April, and September. This area is perfect for those seeking beach relaxation, hiking, and diving experiences. Highlights include breathtaking views of the bay and nearby mountains, offering visitors a unique blend of education and adventure in a picturesque setting.
• Hell's Gate: Located a mere 0.9 miles from Windward Side, Hell's Gate is a small city that captivates visitors with its natural beauty and beach access. The travel experience is moderately seasonal, with peak arrivals from November to January. Hell's Gate is an excellent destination for beach lovers who can enjoy its pristine sandy shores and tranquil nature. This area is perfect for those looking to unwind and soak in the peaceful surroundings, making it a must-visit for a relaxing getaway.

Things to do in Windward Side

Windward Side offers a perfect blend of beach relaxation and outdoor adventures. Visitors can enjoy activities such as hiking scenic trails, diving in vibrant waters, and exploring educational experiences. For those who love golf, there's a golf course to enjoy a relaxing day on the greens. Whether you're seeking stunning views or thrilling adventures, Windward Side has something for everyone.

Shopping

In Windward Side, explore local shops like The Saba Spice Shop for unique spices and The Golden Rock for handcrafted souvenirs. If you're up for a drive, head to the Saba Hardware Store for practical gifts or visit the Saba Market for fresh produce and local crafts.

Recreation

Experience the tranquility of Saba's Wellness Retreat, where you can indulge in rejuvenating spa treatments and yoga sessions surrounded by lush nature. Stroll through the picturesque trails of Windward Side for invigorating hikes and breathtaking views of the Caribbean Sea, perfect for relaxation and reflection.

Adventure

Explore the breathtaking Mount Scenery, the highest point in Saba, offering stunning views after a rewarding hike. For underwater adventures, dive into the crystal-clear waters surrounding Saba, where vibrant coral reefs and diverse marine life await. Don't miss the thrill of rock climbing at the challenging cliffs around the island.

Nightlife

In Windward Side, the nightlife is vibrant and welcoming, featuring cozy bars like The Bottom, where you can enjoy live music and local brews. Nearby, The Saba Arawak Hotel offers a relaxed atmosphere with stunning views, perfect for unwinding after a day of exploration.

Booking tips and Expedia advantages for Windward Side

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windward Side are May and September to 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: The cheapest time to book a hotel in Windward Side is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windward Side is Thursday. The most expensive day to stay in Windward Side is Tuesday.
• Find cheap hotels on Expedia: Explore Expedia’s search tool to customize your travel preferences, such as your budget, preferred location, and the type of hotel you’re looking for. For instance, selecting the Eco-certified option will show you a list of sustainable and eco-friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your Windward Side hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions in and around Windward Side

Windward Side offers a perfect blend of beach relaxation, outdoor adventures, and stunning scenery. Visitors can explore historical museums, majestic mountains, and local galleries, catering to those seeking culture and adventure. Don't miss the charming gingerbread cottages that add a unique touch to the area's appeal. Whether you’re looking for a cultural experience or a scenic getaway, Windward Side has something for everyone.

• Dutch Museum of Saba: Dive into Saba's rich history at the Dutch Museum of Saba, where you can explore the island's culture and heritage. The museum features exhibits that showcase local traditions, artifacts, and the island's unique story, providing a captivating insight into Saba's past.
• Harry L Johnson Museum: This museum offers a deep look into Saba's cultural heritage through engaging exhibits and displays. The Harry L Johnson Museum celebrates local stories and the island's history, making it a perfect stop for those interested in understanding the island's identity.
• Mt Scenery: Experience adventure and breathtaking views at Mt Scenery, the highest point in Saba. Just 0.7 miles from Windward Side, this stunning mountain invites outdoor enthusiasts to hike its trails and enjoy panoramic vistas of the Caribbean Sea.

Best time to go to Windward Side

The best time to visit Windward Side is dependent on what kind of holiday you are seeking. September is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. March is its coolest month on average. At this time, visitor numbers are high and weather is mostly sunny with no rain.

The nearest major airports for your trip to Windward Side

Traveling to Windward Side, SABa, can be done via its major airport, Saba (SAB-Juancho E. Yrausquin), located 1 mile away. Nearby accommodations include The Cottage Club Hotel and Saba Arawak Hotel, both offering comfortable stays. Additionally, El Momo Cottages provides a cozy guesthouse experience. For further options, you can fly into Oranjestad (EUX-F.D. Roosevelt), situated 19 miles from Windward Side, with hotels like Golden Rock Dive And Nature Resort and Quill Gardens Boutique Hotel nearby. Transportation services from these hotels to the airports are convenient, with options like 24-hour shuttles and transfers available for guests.