Find hotels in Windward Side from $128

Top reasons to visit Windward Side

• Outdoor Adventures: Windward Side offers thrilling activities like hiking, diving, and kite surfing, perfect for adventure seekers.
• Stunning Beaches: Relax on sandy beaches and enjoy breathtaking cliffside views that enhance the beautiful landscape.
• Cultural Experiences: Explore local history museums, vibrant galleries, and embrace the unique cultural charm of the area.
• Scenic Tours: Enjoy canoe tours and scenic drives that showcase the stunning natural beauty of Windward Side.
• Cozy Accommodations: Choose from a variety of lodging options, including charming bed and breakfasts and welcoming hotels.

Find great hotels in and around Windward Side

Discover the charm of Windward Side with a variety of lodging options tailored for every traveler. From cozy bed and breakfasts to welcoming hotels, enjoy amenities that cater to beach lovers, business travelers, and pet-friendly vacations. Experience the inviting atmosphere of a club hotel with a friendly interface, majestic lobby, and delightful cottage club options, ensuring a memorable stay in this beautiful destination.

• Saba Arawak Hotel: Nestled in the heart of Windward Side, Saba Arawak Hotel is a 3-star haven for adventurers and business travelers alike. Its business-themed amenities cater to professionals on the go, while the surrounding landscape invites guests to explore the island's natural beauty. Enjoy a range of adventure sports such as snorkeling, fishing, cave exploring, sailing, and hiking—all conveniently located nearby. This hotel perfectly combines productivity with the thrill of outdoor activities, making it an excellent choice for those seeking both work and play.
• The Old Gin House: Located 19 miles from Windward Side, The Old Gin House is a charming 3-star hotel that captures the essence of a beach vacation. With direct access to pristine sandy shores, this property is ideal for sun-seekers and ocean lovers. Guests can unwind in a relaxed atmosphere while enjoying stunning views of the Caribbean Sea. The inviting ambiance and proximity to the beach make this hotel a perfect retreat for those looking to bask in sun and surf.
• El Momo Cottages: Situated in Windward Side, El Momo Cottages offers a unique guesthouse experience with a pet-friendly policy. This cozy accommodation is perfect for travelers who wish to bring their furry companions along on their getaway. With amenities designed for pets, such as free permissibility for some animals, guests can enjoy a comfortable stay without leaving their pets behind. The charming atmosphere and welcoming environment make El Momo Cottages a delightful option for pet owners seeking a memorable vacation.

Where to stay in and around Windward Side

Windward Side offers a stunning blend of sandy beaches and breathtaking cliffside views, perfect for outdoor enthusiasts and relaxation seekers alike. With its warm and sunny climate, travelers can enjoy the scenic beauty and vibrant atmosphere of nearby neighborhoods. From historical sites to luxurious retreats, Windward Side is a romantic getaway that promises a memorable vacation experience amidst its picturesque landscapes and inviting vibes.

• Oranjestad: Oranjestad, located 19 miles from Windward Side, is a vibrant city known for its outdoor activities and stunning beach scenery. The city experiences moderately seasonal traveler arrivals, peaking from November to January. Visitors flock here to enjoy its beautiful resorts and golf courses, making it a perfect spot for relaxation and recreation. Don't miss the local history museum, where you can delve into the island's rich past, or take a leisurely stroll along the picturesque beach and bay, soaking in the breathtaking views.
• The Bottom: Just a mile away from Windward Side, The Bottom is a charming city that offers a delightful blend of culture and outdoor adventures. With traveler arrivals peaking in January, April, and September, this area is ideal for those looking to experience local culture while enjoying recreational activities. Hiking enthusiasts will appreciate the nearby trails, and golfers can enjoy the local golf course. The Bottom also features a lovely beach and a history museum, providing a perfect setting to relax and explore the island's heritage.
• Upper Zion's Hill: Nestled in the vicinity of Windward Side, Upper Zion's Hill is a quaint village that attracts visitors seeking a laid-back beach experience. The area enjoys moderately seasonal traveler arrivals, peaking from November to January. The village is known for its beautiful beaches, including a nudist beach, making it a unique destination for sun-seekers. The serene environment and stunning coastal views make Upper Zion's Hill a perfect spot to unwind and enjoy the natural beauty of the island.

Things to do in Windward Side

Windward Side is the perfect destination for beach lovers and outdoor enthusiasts. Enjoy a variety of activities such as hiking, diving, and scuba diving. You can also try kite surfing, embark on canoe tours, explore nearby islands, go day snorkeling, or take scenic drives to soak in the breathtaking views. Discover the natural beauty and unique experiences that make Windward Side a must-visit location.

Shopping

In Windward Side, explore local shops offering unique gifts and souvenirs, including handcrafted items and island-themed merchandise. If you're up for a drive, visit The Bottom, about 10 miles away, where you'll find additional shops and local markets featuring vibrant crafts and culinary delights.

Recreation

Experience the soothing ambiance of The Saba Spa, where you can indulge in rejuvenating massages and holistic treatments. Afterward, explore the scenic hiking trails around Windward Side, offering stunning views and a chance to connect with nature while enjoying fresh island air.

Adventure

Explore the scenic hiking trails of Mount Scenery, the highest point in Saba, for breathtaking views and lush landscapes. Immerse yourself in the vibrant underwater world while snorkeling or diving at the famous Saba Marine Park, home to stunning coral reefs and diverse marine life.

Nightlife

In Windward Side, the nightlife is vibrant and inviting. Enjoy live music at local bars, savor cocktails at cozy lounges, or try your luck at a small casino. The atmosphere is friendly, making it perfect for mingling with locals and fellow travelers alike.

Booking tips and Expedia advantages for Windward Side

To save money while visiting Windward Side, plan your trip during the cheaper months of May and September to October, and consider booking your hotel about a month in advance for the best rates. Utilize Expedia’s search tool to find eco-friendly accommodations and sort prices from lowest to highest. Look for last-minute deals and combine bookings for flights and activities to save even more. Joining Expedia’s One Key membership can also provide exclusive discounts and future cash rewards. Lastly, aim to check in on a Thursday for the best rates.

• 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. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
• 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 Wednesday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are 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.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Windward Side

Windward Side offers a perfect blend of beaches, outdoor adventures, and stunning scenery for vacationers. Visitors can explore various attractions, including local history museums, scenic mountains, and vibrant galleries. This charming destination is ideal for those seeking cultural experiences and thrilling outdoor activities, making it a great spot for both relaxation and adventure.

• Dutch Museum of Saba: Immerse yourself in the rich history and culture of Saba at the Dutch Museum. This small yet informative museum showcases artifacts and exhibits that highlight the island's heritage, making it a perfect stop for history enthusiasts.
• Harry L Johnson Museum: Another gem in Windward Side, the Harry L Johnson Museum offers a deep dive into Saba's past. With its engaging displays and local stories, it provides visitors with a unique perspective on the island’s cultural evolution.
• Mt Scenery: Experience adventure and breathtaking views at Mt Scenery, located just 0.7 miles from Windward Side. A hike to the summit rewards you with stunning panoramas of the island and surrounding sea, perfect for outdoor lovers and photographers alike.

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 Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	78.4°F (25.8°C)	No Rain	Mostly Sunny	Average	Average
February	77.9°F (25.5°C)	No Rain	Mostly Sunny	Average	Slightly High
March	77.7°F (25.4°C)	No Rain	Mostly Sunny	High	Average
April	78.8°F (26.0°C)	No Rain	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	Average
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	Slightly Low
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

Traveling to Windward Side, Saba, is convenient with two major airports nearby. Saba (SAB-Juancho E. Yrausquin) is just 1 mile away, with nearby accommodations such as The Cottage Club Hotel and Saba Arawak Hotel, both rated 3 stars. For those considering Oranjestad (EUX-F.D. Roosevelt), located 19 miles away, options include the 4-star Golden Rock Dive And Nature Resort and the Quill Gardens Boutique Hotel, also rated 4 stars. Transportation services to both airports include shuttles and transfers from these hotels, making access easy for tourists.