Hotels in Shelter Island

Embrace Serenity: Discover the Enchantment of Shelter Island's Shoreline and History

Nestled between the vibrant North and South Forks of Long Island, Shelter Island is a hidden gem that offers a serene escape steeped in natural beauty. With its pristine beaches, tranquil parks, and charming historic lighthouse, visitors can revel in idyllic landscapes perfect for family outings or romantic retreats. Explore the island’s lush trails, take a refreshing dip in the inviting waters, or indulge in local dining experiences. Whether seeking adventure or relaxation, Shelter Island promises a unique experience that enchants every traveller. Uncover the magic of this off-the-beaten-path destination and create lasting memories.

Discover great hotels near Shelter Island

Shelter Island offers a delightful range of accommodation options, from charming boutique hotels to more luxurious stays with stunning waterfront views. Whether you seek a classic retreat steeped in history or a modern getaway, you'll find inviting spaces that cater to various tastes and budgets. These are some of the hotels preferred by our travellers near Shelter Island:

1. West Neck GuesthouseOpens in a new window: This inviting 3.5-star hotel boasts a commendable guest rating of 8.0 out of 10, making it a delightful choice for leisure travellers seeking comfort and relaxation. With bed and breakfast lodging, it offers a range of dining options including complimentary breakfast and continental breakfast daily. The entertainment amenities, such as cable television and flat-screen televisions, enhance the experience. The positive sentiments highlight the welcoming atmosphere and the enjoyable dining options, making it a fantastic retreat for those looking to unwind in a charming setting.
2. Shelter Island HouseOpens in a new window: A 3.5-star hotel with an impressive guest rating of 8.4 out of 10, this property is tailored for travellers seeking a golf-themed vacation experience. Its amenities cater to those who appreciate family-friendly environments while enjoying a unique stay. Guests can indulge in golf experiences right on the premises, creating memorable moments. The positive feedback reflects the hotel’s appeal as a family-oriented destination, providing a blend of leisure and recreation that enhances the overall journey.
3. House on Chase CreekOpens in a new window: This budget-friendly guesthouse shines with an exceptional guest rating of 9.4 out of 10, making it an ideal choice for leisure travellers who appreciate a distinctive experience. With direct access to the beach and a focus on golf-themed activities, it offers a unique blend of relaxation and recreation. The immaculate accommodations contribute to a serene atmosphere, with sentiments praising the cleanliness and welcoming environment. This property stands out as a charming oasis for those seeking quality comfort and memorable experiences in a picturesque setting.

Where to stay near Shelter Island

Some of the best areas to stay in when visiting Shelter Island are Greenport, Sag Harbor, and Southold. Greenport is ideal for nature lovers and families, offering stunning sunsets and various water activities. Sag Harbor is perfect for boating enthusiasts and those seeking a charming coastal vibe. Southold is known for its wineries and family-friendly atmosphere. For first-time visitors, Greenport is the best choice with its vibrant mix of attractions.

1. GreenportOpens in a new window: Greenport is a charming seaside village that’s perfect for families and nature lovers. With its stunning sunsets and beautiful beaches, it’s a fantastic spot to unwind. You can explore 67 Steps Beach for a relaxing day by the water or visit the East End Seaport Maritime Museum to dive into local maritime history. Greenport’s vibrant port area is ideal for boating excursions, and seasonal festivals add a lively atmosphere to your stay. The scenic ferry rides offer a unique way to experience the surrounding islands, making it a memorable base for your Shelter Island adventure.
2. Sag HarborOpens in a new window: Sag Harbor is a picturesque destination that seamlessly blends maritime charm with a rich cultural scene. The lovely Sag Harbor Marine Park provides a great spot for picnics and outdoor activities, while the nearby East Hampton Main Beach is perfect for sunbathing and swimming. With its quaint streets lined with boutiques and galleries, you can enjoy some delightful shopping. The area is renowned for its sailing opportunities, allowing you to embrace the coastal lifestyle. Whether you're biking along the waterfront or soaking in the stunning sunsets, Sag Harbor offers a relaxed yet vibrant atmosphere.
3. SoutholdOpens in a new window: Southold is known for its beautiful wineries and family-friendly activities, making it a great choice for those looking to relax and unwind. The stunning gardens and monuments in the area provide lovely spots for leisurely strolls. With plenty of sunny weather, you can enjoy the beaches and outdoor spaces. The local vibe is welcoming and laid-back, perfect for families wanting to spend quality time together. Southold’s charming atmosphere and access to nature make it a lovely retreat for a more peaceful getaway.

Things to do in Shelter Island

Nestled between lush forests and tranquil waters, Shelter Island offers a delightful escape for nature lovers. Enjoy kayaking along serene shores, hiking through scenic trails, or simply basking on sun-kissed beaches. With its charming parks and vibrant outdoor activities, it’s an inviting haven for all who visit.

• Sag Harbor Marine ParkOpens in a new window – Head to Sag Harbor Marine Park, where you can take in the sights at this bustling marina. It's an excellent spot for a leisurely stroll or to watch boats come and go, providing a delightful atmosphere for both nature enthusiasts and those interested in maritime activities.
• Horton Lane BeachOpens in a new window – Spend a sunny day at Horton Lane Beach, where the golden sands and gentle waves invite you to relax. This beach is perfect for sunbathing or enjoying a refreshing swim. Pack a picnic and make the most of your day by the sea.
• Orient Point County ParkOpens in a new window – Explore the natural beauty at Orient Point County Park, an urban park that showcases the region's diverse ecosystems. You can wander through scenic trails, enjoy birdwatching, or simply take in the tranquillity of the surroundings.
• 67 Steps BeachOpens in a new window – Discover the charm of 67 Steps Beach, a unique spot with a series of steps leading down to the shore. It's a wonderful place to enjoy a quiet afternoon, whether you're building sandcastles or taking a refreshing dip in the water.
• Crescent BeachOpens in a new window – Visit Crescent Beach, known for its inviting shoreline and stunning views. This beach offers a relaxing atmosphere, perfect for families or couples looking to unwind. Don't forget your camera to capture the picturesque moments.

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 prices are typically lower. For a budget-friendly getaway, staying for at least 2 to 3 days is ideal to fully appreciate the rich history and cultural landmarks of the area. Visitors can explore scenic spots, enjoy kayaking in the beautiful natural parks, and visit historical museums, making it a great value for money trip that combines relaxation with exploration.
2. Look for last-minute deals on Hotels.com: To uncover last-minute deals to Shelter Island on Hotels.com, begin by exploring the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections, where you may discover discounted hotel rates as your travel date approaches. It’s wise to enable email alerts or push notifications from Hotels.com to stay informed about flash sales and special promotions, helping you to seize savings opportunities. Additionally, the Smart ShoppingOpens in a new window tool available via the app allows you to compare hotel prices and amenities, ensuring you’re well-equipped to make informed choices. If prices drop or rooms become available, you could be among the first to know, making your last-minute escape easier.
3. Be flexible with dates: Prices can fluctuate based on factors such as the hotel's location, star rating, and the time of year, so being flexible with your travel dates may help you find better rates for your stay in a Shelter Island hotel. For those seeking distinctive experiences, boutique hotels often provide a more personalised touch and sometimes offer improved value. When you book with Hotels.com, we will inform you if the price for your chosen dates is above or below the average. If the price leans towards the higher end, we will suggest alternative dates that could be more affordable, assisting you in potentially discovering a better deal.
4. Consider your location: Staying nearer to key attractions or city centres may provide convenience, but it often tends to come with higher costs. For more budget-friendly options, consider hotels in less central areas or neighbourhoods, striking a balance between price and accessibility to the places you wish to visit. You might also explore independent hotels further afield, which are more likely to offer a more authentic and cost-effective 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 tends to be the wettest month. The peak travel months to visit Shelter Island are June to August, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, October to December are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny to mostly cloudy conditions.