Hotels in Shelter Island

Serenity Awaits: Discover the Hidden Treasures of Shelter Island

Escape to Shelter Island, New York, where serene natural beauty meets charming coastal allure. This hidden gem, nestled between the North and South Forks of Long Island, offers breathtaking views and tranquil beaches like Sunset Beach, perfect for romantic sunsets. Explore lush nature trails in Mashomack Preserve or indulge in art at local galleries and museums. With its quaint village atmosphere, historic Shelter Island Heights, and laid-back vibe, it's an ideal retreat for nature lovers and those seeking a peaceful getaway. Unwind, recharge, and experience the unique charm of Shelter Island—a sanctuary off the beaten path.

Discover great hotels in Shelter Island

Shelter Island offers a range of accommodations, from charming boutique hotels to luxurious seaside retreats. Visitors can enjoy well-appointed guest rooms with stunning views, creating an ideal setting for relaxation and exploration. Whether you prefer a cozy inn or a more upscale stay, you'll find inviting options throughout the island. Here are some of the most popular hotels with our travelers in Shelter Island:

1. West Neck GuesthouseOpens in a new window: This inviting 3.5-star Bed and Breakfast offers a comfortable retreat, featuring complimentary breakfast options that include daily continental selections. Guests can unwind in their rooms equipped with modern entertainment amenities such as a flat-screen television and cable options. This hotel is perfect for leisure travelers seeking a cozy atmosphere and personalized service, making it a delightful choice for those looking to enjoy a memorable getaway.
2. Shelter Island HouseOpens in a new window: With a focus on family and golf-themed vacations, this 3.5-star hotel promises an engaging experience for leisure travelers looking to indulge in a golf-centric holiday. Guests can take advantage of the on-site golf facilities and enjoy amenities tailored for families, such as complimentary cribs. The hotel’s welcoming environment and recreational offerings create a unique and enjoyable ambiance for those seeking a blend of relaxation and activity while surrounded by picturesque landscapes.
3. House on Chase CreekOpens in a new window: This charming 2.5-star guesthouse caters to beach and golf enthusiasts, providing direct access to sandy shores and golf activities. The guesthouse exudes a laid-back vibe, perfect for leisure travelers wanting to immerse themselves in nature. With a focus on the beach and golfing experiences, this property stands out as a cozy escape for those seeking sun, sand, and outdoor activities in a friendly and relaxed atmosphere.

Top locations to stay in Shelter Island

Some of the best areas to stay in Shelter Island, New York, are Greenport, Sag Harbor, and Bridgehampton. Greenport offers beautiful natural landscapes and outdoor activities, Sag Harbor boasts a charming maritime atmosphere with boating opportunities, and Bridgehampton is known for its equestrian culture and upscale vibe. For first-time visitors, Sag Harbor is the most appealing choice with its vibrant harbor scene.

1. GreenportOpens in a new window: Greenport is a charming seaside village perfect for nature lovers and those seeking a laid-back atmosphere. The area is known for its stunning waterfront views, picturesque parks, and lush gardens. You can explore the scenic beaches or enjoy a leisurely stroll through the local shops that showcase artisanal goods and unique souvenirs. Greenport also offers a delightful selection of cultural attractions, including art galleries and seasonal festivals that celebrate the community's maritime heritage.
2. Sag HarborOpens in a new window: Sag Harbor is a historic whaling port that boasts a vibrant arts scene and a rich maritime history. This quaint village is ideal for travelers seeking a mix of culture and relaxation. Wander through the charming streets lined with boutiques, art galleries, and cafes. The picturesque waterfront is perfect for leisurely walks, and you can dive into local history at the Sag Harbor Whaling Museum. The town also hosts various cultural events throughout the year, making it a lively spot to experience local artistry.
3. BridgehamptonOpens in a new window: Bridgehampton is known for its equestrian culture and stunning landscapes, making it a delightful destination for those who appreciate the outdoors. The area offers beautiful horse farms and scenic trails ideal for leisurely rides or hikes. You can also explore local vineyards and enjoy wine tasting experiences amid the stunning countryside. With its charming boutiques and seasonal farmer's market, Bridgehampton provides a perfect blend of relaxation and local flavor, making it a great place to unwind and soak in the natural beauty.

Things to do in Shelter Island

Escape to Shelter Island, where sandy beaches meet lush forests and serene parks. Enjoy kayaking on tranquil waters, hiking scenic trails, or bowling with friends. As the sun sets, relish breathtaking views that make this charming oasis a must-visit destination for nature lovers and outdoor enthusiasts alike.

• 67 Steps BeachOpens in a new window – Spend a relaxing day at this serene beach, where you can bask in the sun, enjoy the gentle waves, and take leisurely strolls along the shore. It's a great spot for a beach picnic or simply unwinding in a picturesque setting.
• LongHouse ReserveOpens in a new window – Discover this enchanting sculpture garden that beautifully blends art and nature. Wander through lush landscapes dotted with captivating sculptures, each telling a unique story. It’s a perfect place to appreciate creativity while enjoying the tranquility of the surroundings.
• Sag Harbor Marine ParkOpens in a new window – Visit this vibrant marina, ideal for boating enthusiasts and those who love being by the water. Watch the boats come and go, enjoy a waterfront picnic, or take part in various water activities while soaking up the fresh sea breeze.
• Orient Point County ParkOpens in a new window – Explore this urban park that offers a mix of natural beauty and recreational opportunities. Stroll through scenic trails, enjoy bird watching, or simply take in the stunning views of the surrounding landscapes.
• Orient Beach State ParkOpens in a new window – Head to this beautiful beach park for a day filled with sun and fun. Swim, sunbathe, or take a scenic walk along the shore. The park provides a perfect backdrop for outdoor activities and family gatherings.

4 tips for savvy savings when booking a hotel in Shelter Island

1. Book for the cheapest times: The most affordable time to visit Shelter Island is from January to March, when hotel rates are generally lower. For a budget-friendly trip, staying for at least 2 to 3 days is recommended to fully experience the island's key landmarks, cultural sites, and natural beauty. During your visit, you can explore historical attractions, enjoy scenic views, and engage in activities like kayaking, bowling, and leisurely walks in natural parks. This duration allows you to appreciate the rich history and vibrant culture of Shelter Island while getting great value for your money.
2. Look for last-minute deals on Hotels.com: To explore last-minute deals to Shelter Island, visit the DealsOpens in a new window or Last-Minute Deals section on Hotels.com, where you may discover discounted rates on hotels as your travel date approaches. Enabling email alerts or push notifications can keep you informed about flash sales and special promotions, helping you save on your stay. Additionally, Smart Shopping is a useful comparison tool available in the app, allowing you to compare hotel prices and amenities effortlessly. By staying updated on price drops and availability, you’re more likely to seize a great last-minute getaway.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates could help you save on your stay at a Shelter Island hotel. If you're looking for something special, boutique hotels can provide a more personalized experience and may offer better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher side, we’ll recommend alternative dates that might be more affordable, increasing the likelihood that you’ll find a great deal.
4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. For more budget-friendly options, consider hotels in less central neighborhoods, where you can find a balance between cost and accessibility to the sights you want to see. Additionally, you might want to look into independent hotels a bit further out, as they usually tend to be more affordable and can offer a more authentic experience.

Best time to go to Shelter Island

Shelter Island experiences its lowest average temperature in January, at 35.6°F (2.0°C), while August is the hottest month, with an average temperature of 73.4°F (23.0°C). October are typically the wettest months. If you’re looking to soak up the lively atmosphere in Shelter Island, June to August are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, with light rainfall. However, if you prefer a more relaxed experience, October to December are perfect for a quieter getaway, marked by light rainfall and mostly sunny to mostly cloudy conditions.