Shelter IslandBoutique Hotels with Entertainment

List Of Best Boutique Hotels with Entertainment Shelter Island

We have created a list with the best boutique hotels with entertainment in Shelter Island, USA. Hope you enjoy it. We think it might be the best of its kind around

boutique hotels in Shelter Island
Hotel
207 Front Street, Greenport, NY 11944, USA

Welcome to The Menhaden Hotel, located in the charming town of Greenport! We’re just a short drive away from Splish Splash, which is about 41 km from here. Our hotel offers a warm and welcoming experience, with amenities designed to make your stay comfortable and enjoyable. We provide concierge services to assist you with anything you need during your visit. For those with allergies, we have allergy-free rooms available. If you enjoy cycling, feel free to borrow one of our free bikes to explore the beautiful surroundings. Stay connected with complimentary WiFi throughout the hotel, and don't forget to relax on our lovely terrace. At The Menhaden, we strive to create a friendly and inclusive atmosphere for everyone. We look forward to welcoming you soon!

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Boutique hotel amenities:

Entertainment • Restaurant • Child Friendly • Oceanfront • Ocean View • Wellness Facilities • Sports/Activities

boutique hotels in Shelter Island
Hotel
31 W. Water Street, Sag Harbor, NY 11963, USA

Welcome to Baron's Cove, a welcoming retreat located in the charming town of Sag Harbor, New York. Here, you can enjoy delicious meals at our on-site restaurant and take a refreshing dip in our seasonal saltwater swimming pool. We’re committed to making your stay comfortable with complimentary WiFi throughout the property and free parking for our guests. We look forward to providing you with a relaxing and enjoyable experience!

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Boutique hotel amenities:

Business Services • Transportation/Shuttle • Wellness Facilities • Oceanfront • Spa • Entertainment • Ocean View • Sports/Activities

boutique hotels in Shelter Island
Hotel
91 Hill Street, Southampton, NY 11968, USA

Welcome to our Long Island hotel, where you can enjoy the beauty of over 5 acres of lovely gardens and lawns. We invite you to relax at our modern American restaurant, which offers convenient poolside service for your comfort. Plus, during the summer months, we provide free transportation to Cooper’s Beach, making it easy for you to soak up the sun and enjoy the ocean. We look forward to making your stay enjoyable!

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Boutique hotel amenities:

Entertainment • Restaurant • Transportation/Shuttle • Business Services • Wellness Facilities • Ocean View • Sports/Activities • Oceanfront

boutique hotels in Shelter Island
Hotel
490 Pantigo Road, East Hampton, NY 11937, USA

Welcome to Journey East Hampton! Nestled just 1.8 km from the beautiful Indian Wells Beach, we offer a warm and inviting place for you to stay. Our accommodations include a seasonal outdoor swimming pool where you can relax and unwind, as well as free private parking to make your stay hassle-free. Enjoy the peaceful garden or gather with friends and family in our shared lounge. We are dedicated to creating a comfortable and enjoyable experience for all our guests. Come and make unforgettable memories with us!

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Boutique hotel amenities:

Entertainment • Oceanfront • Child Friendly • Ocean View

boutique hotels in Shelter Island
Hotel
273 Main Street, PO box 799, Amagansett, NY 11930, USA

Welcome to The Roundtree, Amagansett, located in the charming Village of Amagansett in East Hampton. Here, you can enjoy a variety of amenities designed for your comfort and enjoyment. Take advantage of our complimentary bikes to explore the beautiful surroundings, relax in our garden, or fire up the BBQ facilities for a delightful meal outdoors. We also offer free WiFi so you can stay connected during your visit. Plus, there’s no need to worry about parking—free private parking is available on site for your convenience. We look forward to making your stay as enjoyable as possible!

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Boutique hotel amenities:

Restaurant • Business Services • Wellness Facilities • Ocean View • Oceanfront • Sports/Activities • Child Friendly • Entertainment

boutique hotels in Shelter Island
Hotel
36 MAIN ST, Essex, CT 06426, USA

The Griswold Inn is a welcoming place in Essex where you can relax and feel at home. It features a lovely garden, a cozy shared lounge, and a terrace where you can enjoy fresh air. There’s also a bar where you can unwind with a drink. If you're interested in exploring the area, the Goodspeed Opera House is just about 18 km away, and Wesleyan University is 35 km from us. We offer free WiFi to help you stay connected during your stay. Whether you’re here for a getaway or to explore, we’re here to make your experience enjoyable!

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Boutique hotel amenities:

Child Friendly • Sports/Activities • Entertainment • Business Services • Restaurant

boutique hotels in Shelter Island
Hotel
94 W Wharf Rd, Madison, CT 06443-2905, USA

Welcome to Madison Beach Hotel, part of the Curio Collection by Hilton! We’re excited to offer you a comfortable stay in beautiful Madison, just a short distance from New Haven. During your visit, you'll enjoy complimentary WiFi to keep you connected. Each of our cozy rooms is equipped with a TV and has its own private bathroom for your privacy and convenience. We look forward to making your experience enjoyable and memorable!

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Boutique hotel amenities:

Ocean View • Entertainment • Spa • Oceanfront • Sports/Activities • Wellness Facilities • Business Services • Private Beach

boutique hotels in Shelter Island
Resort
290 Old Montauk Highway, Montauk, NY 11954, USA

Gurney's is a beloved destination located on one of the most beautiful oceanfront areas in Montauk. It's special because it's the only resort in Montauk that welcomes guests all year round. Here, you can enjoy direct access to a stunning 2,000-foot private beach, making it easy for everyone to savor the sun and sea. Whether you're looking for a relaxing getaway or a fun-filled adventure, Gurney's is designed to cater to your needs and create unforgettable experiences for all visitors.

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Boutique hotel amenities:

Oceanfront • Private Beach • Ocean View • Sports/Activities • Business Services • Private Pool • Entertainment • Transportation/Shuttle

boutique hotels in Shelter Island
Hotel
47 Quogue Street, Quogue, NY 11959, USA

Welcome to The Quogue Club, located in the charming village of Quogue, just 39 kilometers from East Hampton. We are delighted to offer cozy, air-conditioned rooms with complimentary WiFi to ensure your comfort and connectivity throughout your stay. Feel free to unwind at our on-site bar, where you can relax and enjoy a variety of beverages. We also provide free private parking for your convenience, so you can explore the area without any hassle. At The Quogue Club, we prioritize your needs and strive to create a welcoming atmosphere for all our guests. We look forward to making your visit special!

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Boutique hotel amenities:

Child Friendly • Entertainment • Sports/Activities • Wellness Facilities • Business Services • Restaurant

Other cool accommodation lists for Shelter Island:

Most booked boutique hotels with Entertainment in Shelter Island

boutique hotels in Shelter Island
36 MAIN ST, Essex, CT 06426, United States of America
8.6
254 reviews
From $195
boutique hotels in Shelter Island
91 Hill Street, Southampton, NY 11968, United States of America
8.3
234 reviews
From $6038
boutique hotels in Shelter Island
290 Old Montauk Highway, Montauk, NY 11954, United States of America
8
198 reviews
From $525

Budget Boutique Hotels with Entertainment in Shelter Island

boutique hotels in Shelter Island
36 MAIN ST, Essex, CT 06426, United States of America
8.6
254 reviews
From $195
boutique hotels in Shelter Island
94 W Wharf Rd, Madison, CT 06443-2905, United States of America
9
43 reviews
From $288
boutique hotels in Shelter Island
207 Front Street, Greenport, NY 11944, United States of America
9.3
120 reviews
From $329

Compare the Top Boutique Hotels with Entertainment in Shelter Island – Addresses, Prices, Stars, Rating, and Review Count

Hotel Name Address Price ($) Star Rating Review Count Book
The Menhaden Hotel 207 Front Street, Greenport, NY 11944, USA 329 4 9.3 120
Baron's Cove 31 W. Water Street, Sag Harbor, NY 11963, USA 920 4 8.5 122
Southampton Inn 91 Hill Street, Southampton, NY 11968, USA 6038 4 8.3 234
Journey East Hampton 490 Pantigo Road, East Hampton, NY 11937, USA 800 4 8 125
The Roundtree, Amagansett 273 Main Street, PO box 799, Amagansett, NY 11930, USA 1462 5 9.5 30
The Griswold Inn 36 MAIN ST, Essex, CT 06426, USA 195 2 8.6 254
Madison Beach Hotel, Curio Collection by Hilton 94 W Wharf Rd, Madison, CT 06443-2905, USA 288 4 9 43
Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway, Montauk, NY 11954, USA 525 5 8 198
The Quogue Club 47 Quogue Street, Quogue, NY 11959, USA 880 5 9.1 47

Note: The prices for each boutique hotels in Shelter Island do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here>) to get the latest prices.

Top 8 Attractions in the Shelter Island, USA

Welcome to Shelter Island: Experience a lavish getaway with a luxury or boutique stay in Shelter Island, USA, where captivating natural beauty and charming accommodations await you.

Shelter Island Historical Society Museum: Dive into the rich heritage of the island by visiting this museum that showcases artifacts and stories from its storied past.

Mashomack Preserve: Explore over 2,000 acres of pristine nature at Mashomack Preserve, where hiking trails lead you through stunning landscapes and diverse wildlife.

Shell Beach: Relax on the idyllic shores of Shell Beach, a picturesque spot ideal for sunbathing and enjoying breathtaking sunsets during your boutique stay in Shelter Island, USA.

Hay Beach: Unwind at Hay Beach, a tranquil setting perfect for swimming, picnicking, and taking leisurely strolls along the shoreline.

North Ferry: Take a scenic ride on the North Ferry, which not only connects Shelter Island to the mainland but also offers stunning views of the surrounding waters.

Vanderbilt Museum: Visit this opulent estate that displays exquisite architecture and beautiful gardens, providing insight into the lifestyle of the wealthy in the early 20th century.

Sunset Beach: Witness magical sunsets at Sunset Beach, an enchanting location where you can enjoy fine dining and beachfront relaxation after a day of exploration.

Frequently Asked Questions

Popular boutique hotels in Shelter Island that have a pool include:

  • Gurney's Montauk Resort & Seawater Spa.- Review Count: 198, Rating: 8

Transportation/Shuttle service is available at the following boutique hotels in Shelter Island:

  • Baron's Cove.- Review Count: 122, Rating: 8.5
  • Southampton Inn.- Review Count: 234, Rating: 8.3
  • Gurney's Montauk Resort & Seawater Spa.- Review Count: 198, Rating: 8

A spa is available to guests at the following boutique hotels in Shelter Island:

  • Baron's Cove.- Review Count: 122, Rating: 8.5
  • Madison Beach Hotel, Curio Collection by Hilton.- Review Count: 43, Rating: 9
  • Gurney's Montauk Resort & Seawater Spa.- Review Count: 198, Rating: 8

Families traveling in Shelter Island enjoyed their stay at the following boutique hotels:

  • The Menhaden Hotel.- Review Count: 120, Rating: 9.3
  • Baron's Cove.- Review Count: 122, Rating: 8.5
  • Southampton Inn.- Review Count: 234, Rating: 8.3

Some of the best boutique hotels in Shelter Island are:

  • Gurney's Montauk Resort & Seawater Spa.- Review Count: 198, Rating: 8
  • The Quogue Club.- Review Count: 47, Rating: 9.1
  • The Roundtree, Amagansett.- Review Count: 30, Rating: 9.5