The Best Hotels Closest to Shelter Island Whale's Tail in Shelter Island - 2026 Updated Prices

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Our top choices for Shelter Island Whale's Tail hotels

A serene landscape with a calm body of water reflecting trees with autumn foliage.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

A sign for 'House on Chase Creek' with a duck illustration.

A serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.

1. House on Chase Creek

1.2 mi from Shelter Island Whale's Tail

Calvin

£207

includes taxes & fees

9 Sept - 10 Sept

An outdoor patio area with string lights, tables, chairs, and a fire pit.

A staircase with wooden balusters and a white wall.

A large, white building with multiple windows and a prominent tree in the foreground.

A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

2. The Chequit

1.3 mi from Shelter Island Whale's Tail

Kathleen

£189

includes taxes & fees

8 Sept - 9 Sept

3. Shelter Island House

1.5 mi from Shelter Island Whale's Tail

Dorothy

£267

includes taxes & fees

7 Sept - 8 Sept

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

A backyard with a large chessboard, outdoor furniture, and a house.

A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.

A beach with a wooden walkway along the shore, calm water, and a sunset sky.

4. West Neck Guesthouse

1.2 mi from Shelter Island Whale's Tail

Allie

£264

includes taxes & fees

7 Sept - 8 Sept

A beach with waves gently lapping onto the shore.

A patio with four wicker chairs arranged around a round table with a fire pit in the center, set in a grassy outdoor area with trees and a fence in the background.

A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."

A modern bedroom with a bed, a desk with a chair, a television, and a large mirror.

5. The Roundtree, Amagansett

12.1 mi from Shelter Island Whale's Tail

Ryan

£616

includes taxes & fees

1 Oct - 2 Oct

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

6. The Menhaden

2.4 mi from Shelter Island Whale's Tail

Lisa

£400

includes taxes & fees

7 Sept - 8 Sept

An outdoor dining area with trees and tables under string lights.

A white house with a sign reading "The 1770 House Restaurant & Inn."

A living room with a fireplace, a television mounted above it, and a dining area in the background.

A restaurant with wooden beams, tables with white tablecloths, and a bar area.

7. The 1770 House Restaurant & Inn

11 mi from Shelter Island Whale's Tail

Lisa

£494

includes taxes & fees

21 Sept - 22 Sept

A modern house with a deck, outdoor seating, and a fire pit.

A modern living room with a sofa, a dining table, and a kitchen area in the background.

A tented accommodation with a bed, television, and a small table with a chair.

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

8. North Fork Resort

3.2 mi from Shelter Island Whale's Tail

Lisa

£253

includes taxes & fees

7 Sept - 8 Sept

A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

A sliding glass door leading to an outdoor deck with a view of a swimming pool and greenery.

A large, modern house with a swimming pool, surrounded by lush greenery and trees.

A residential area with houses, a wooden deck, and a garden with pink flowers.

9. East Hampton Art House Bed & Breakfast

9.1 mi from Shelter Island Whale's Tail

IVAN

£577

includes taxes & fees

1 Oct - 2 Oct

A beach chair with a striped cushion and a bag with a floral design.

A dining area with a table set for two, wicker chairs, a painting of sailboats, and a wooden ceiling with a grid pattern.

A two-story white house with a brick pathway leading to the front door, surrounded by a white picket fence and a flag.

A person riding a bicycle with a basket on a road.

10. The Hedges Inn

11.2 mi from Shelter Island Whale's Tail

Lauren

£499

includes taxes & fees

8 Sept - 9 Sept

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

A storefront with a sign reading "THE SHOALS".

11. The Shoals Suites and Slips

3.7 mi from Shelter Island Whale's Tail

Melissa

£189

includes taxes & fees

1 Oct - 2 Oct

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

A restaurant with a signboard listing its hours of operation.

A bar area with stools, a shelf with glasses, and decorative plants.

12. Zey Hotel

2.4 mi from Shelter Island Whale's Tail

shaun

£142

includes taxes & fees

7 Sept - 8 Sept

A deck with outdoor seating, overlooking a body of water with a sunset view.

A restaurant with green booths, wooden chairs, and round tables.

A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

13. The Pridwin Hotel

2.3 mi from Shelter Island Whale's Tail

Anna

£495

includes taxes & fees

8 Sept - 9 Sept

A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

A living room with a fireplace, two sofas, a coffee table, and a chair.

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

14. Journey East Hampton

11.7 mi from Shelter Island Whale's Tail

NAKUL

£311

includes taxes & fees

7 Sept - 8 Sept

A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.

A cozy interior with a bar area, seating, and a fireplace.

A spacious room with a wooden bar area, shelves with books and decorative items, a patterned wall, and a large window.

A bedroom with a bed, bedside tables, a nightstand, a lamp, a painting, a robe, and a bathroom door.

15. Oyster Estate

2.4 mi from Shelter Island Whale's Tail

Jenny

£323

includes taxes & fees

7 Sept - 8 Sept

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

16. A Room At The Beach

9.6 mi from Shelter Island Whale's Tail

"I absolutely loved my stay at **A Room at the Beach** in Bridgehampton. Every detail of the property feels thoughtfully designed, creating an atmosphere that is both elegant and incredibly relaxing. The rooms are stylish, comfortable, and well appointed. They strike the perfect balance between luxury and warmth. What really sets this property apart, though, are the charming grounds. They've created gathering spaces that invite you to pause, read, enjoy a morning coffee, and take in the...

Barbara

£338

includes taxes & fees

30 Sept - 1 Oct

17. East Hampton House Resort

11.3 mi from Shelter Island Whale's Tail

Suzette

£229

includes taxes & fees

28 Sept - 29 Sept

18. Cliffside Resort Condominiums

3.4 mi from Shelter Island Whale's Tail

Christine

£313

includes taxes & fees

27 Sept - 28 Sept

A beach with a lifeguard tower, sandy dunes, and the ocean.

A large, white building with a green awning, surrounded by well-maintained lawns and colorful flower beds.

A large white building with green shutters, surrounded by lush greenery and hydrangea flowers.

A breakfast buffet table with various pastries and fruits, set against a backdrop of large windows overlooking a garden.

19. The Huntting Inn

11 mi from Shelter Island Whale's Tail

James Patrick

£457

includes taxes & fees

7 Sept - 8 Sept

A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

A large, white, two-story building with a covered porch and a bicycle parked in front.

A bar area with shelves stocked with various bottles and glasses.

A modern hotel room with a bed, bedside table, and a view of the garden.

20. Topping Rose House

9.7 mi from Shelter Island Whale's Tail

Adam

£767

includes taxes & fees

7 Sept - 8 Sept

View all properties

Compare popular hotels close to Shelter Island Whale's Tail

Property	Property class	Guest rating
House on Chase Creek	9.4 Exceptional 86 reviews	View
The Chequit	9.2 Wonderful 54 reviews	View
Shelter Island House	8.4 Very good 65 reviews	View
West Neck Guesthouse	8.2 Very good 46 reviews	View
The Roundtree, Amagansett	9.8 Exceptional 100 reviews	View

Top Shelter Island Whale's Tail Hotel Reviews

Bright and Spacious Summer Home Steps from the Beach

10/10 Excellent

"BEAUTIFUL HOME! perfect for a friends getaway with my dog. Kate's home is spacious and has beautiful views of the water and trees from the front deck, living room, kitchen and some of the bedrooms. The kitchen has high-end appliances with everything you'd need for cooking . Kate also has plenty of beach towels, chairs and umbrellas . The shower was amazing and the beds very comfortable . We particularly enjoyed morning walks on the beach directly across from her home and my friends enjoyed bike rides on the bikes that are at the home. Kate was extremely pleasant, responsive and a pleasure to communicate with. We were so sad to leave her home and can't wait to return next year."

Shelter Island House

10/10 Excellent

"I’m"

Zey Hotel

10/10 Excellent

"The staff was very helpful and courteous."

Waterfront House With Dock And Private Beach

10/10 Excellent

"Beautiful waterfront view and aShort walk to the beach- perfect Shelter Island getaway!"

Huge Island Getaway Pool Hot Tub Walk To Beach

8/10 Good

"Great island with plenty of good restaurants.The host was extremely friendly and had great and prompt communication.Lovely house based upon the photos. The house was beautiful at one time. It’s tired and in need of some TLC. There were physical signs of water damage that was patched and left as is. Sliding doors do not lock but are held closed with sticks of wood. The main master bath tub was not working and there is mold in shower. Washing machine leaks. The gas stove did not fully work properly. Half of the bbq burners did not work. On the good note there was plenty of room to roam inside and outside. Several dining areas in house. Great house to enjoy. The pool was also lovely and comfortable. All in all it’s a nice rental, but overpriced for its current condition… I do hope the house is repaired and updated as it can be a fun place to stay."

Work and Play Special! Extended Stay Discount

10/10 Excellent

"Ingrid and Bobby’s home is like a little magical oasis. You’re surrounded by natural beauty with deer wondering about and a pond filled with little turtles. The beds are so comfortable! Better than a hotel! The home looks small on the outside but there’s more than enough room on the inside with lots of different areas to hang inside and out. We stayed there with our three children and they spent hours and hours in the salt water pool. They have speakers all around that you can connect to. Ingrid responded to every message immediately and check in was seamless. Highly recommend! We hope to come back next year"

House on Chase Creek

10/10 Excellent

"Nice owner.. convenient location"

Other attractions near Shelter Island Whale's Tail

Wades Beach

10.0/10 (1 review)

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

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Sylvester Manor

8.8/10 (3 reviews)

You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.

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Shelter Island Historical Society

8.0/10 (1 review)

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

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Havens House

You can spend an afternoon studying the exhibits at Havens House during your travels in Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

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Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

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Menhadden Lane Beach

8.8/10 (3 reviews)

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?

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Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

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Shelter Island Country Club

10.0/10 (3 reviews)

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.

See properties

Frequently asked questions

What are the top-rated hotels near Shelter Island Whale's Tail?

Discovering top-rated hotels near Shelter Island Whale's Tail can enhance your stay with comfort and stunning views.Greenport renovated farmhouseGreenport renovated farmhouse is a charming retreat located just 6.6 km from Shelter Island Whale's Tail, with a perfect review rating of 10. This historic hotel features a spacious kitchen with modern amenities like a dishwasher and refrigerator, ideal for preparing meals. Guests can enjoy the lovely patio, perfect for relaxation, and take advantage of nearby activities such as kayaking and windsurfing. With its romantic ambiance and nearby local wineries, it promises a delightful experience for travellers.American Beech - Luxury 2 Bedroom Apartment 10Located only 5.6 km from Shelter Island Whale's Tail, American Beech - Luxury 2 Bedroom Apartment 10 offers a luxurious stay with an impressive review rating of 10. This two-bedroom apartment features inviting amenities such as a cozy fireplace and a charming patio for unwinding after a day of exploring. Guests can indulge in a complimentary breakfast, making it a perfect start to your day. The romantic setting is ideal for couples looking for a memorable getaway.Fordham HouseFordham House, rated 10 by travellers, is a delightful 3-star hotel situated just 6.3 km from Shelter Island Whale's Tail. Guests can enjoy a complimentary full breakfast on weekends, along with premium bedding for a restful night. The house is conveniently located near the beach, providing easy access for sun-seekers. With free self-parking and designer toiletries, it ensures a comfortable and convenient stay for all travellers.

How much is a hotel near Shelter Island Whale's Tail?

Staying near Shelter Island Whale's Tail is a treat, with plenty of hotels from £142 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

What are the most popular family-friendly hotels near Shelter Island Whale's Tail?

Discover the ideal family-friendly hotels near Shelter Island Whale's Tail that cater to fun and relaxation for all ages.Greenport renovated farmhouseJust 6.6 km from Shelter Island Whale's Tail, this charming farmhouse is rated an impressive 10 by travellers. It features a fully-equipped kitchen, perfect for family meals, and a spacious garden for children to play. With amenities like a TravelCrib, stair gate, and games for kids, families will feel right at home. This hotel also offers a patio for outdoor gatherings and is close to paddleboating and nearby beaches.The Pridwin HotelLocated only 4.0 km from Shelter Island Whale's Tail, The Pridwin Hotel holds a great traveler rating score of 9.4 and is a delightful 4-star option. This hotel is ideal for families, offering a pool with a safety gate and a daily kids' menu at the restaurant. Guests can enjoy complimentary breakfast and access to a game room, ensuring fun-filled days. The hotel also features a stunning beach area and on-site spa services for a relaxing family getaway.Shelter Island HouseShelter Island House is just 2.7 km from Shelter Island Whale's Tail and boasts a solid 8.4 travellers' rating. This 3.5-star hotel is family-friendly with amenities including a free crib, a kitchen for family cooking, and a lovely garden for outdoor activities. Guests appreciate the complimentary breakfast and the nearby local beaches, making it a convenient choice for families looking to explore and relax.

Which hotels near Shelter Island Whale's Tail offer the best views?

Discover the best hotels with stunning views near Shelter Island Whale's Tail that will elevate your stay on this picturesque island.The Pridwin HotelThe Pridwin Hotel, rated 9.4 by travellers, is a charming 4-star retreat located just 4.0 km from Shelter Island Whale's Tail. Guests can indulge in wellness treatments at the onsite spa, enjoy delicious meals with ocean views at the restaurant, and relax by the pool. The hotel features ocean views from many rooms, enhancing the coastal experience. Free breakfast and beach access add to the allure of this lovely hotel.The Harbor Front InnWith a review rating of 8.8, The Harbor Front Inn is a cozy 3.5-star hotel situated 5.1 km from Shelter Island Whale's Tail. This inn offers travellers a charming terrace and cozy rooms with ocean views. Amenities include a refreshing pool, complimentary daily breakfast, and beach towels for your seaside adventures. The inviting atmosphere and convenient location make it a perfect choice for travellers seeking beautiful vistas.Silver Sands Motel & Beach BungalowsSilver Sands Motel & Beach Bungalows boasts an impressive review rating of 9.8 and is a delightful 4-star option located 6.8 km from Shelter Island Whale's Tail. Guests can savor meals at the beachfront restaurant while enjoying breathtaking sea views. The hotel offers beach access, a garden, and various relaxation options including massage services. With its unique bungalows and nearby the beach, it provides a memorable getaway for all travellers.

What are the best affordable hotels near Shelter Island Whale's Tail?

For travellers seeking affordable accommodations near Shelter Island Whale's Tail, these top-rated options offer great value without compromising comfort.Greenport renovated farmhouseGreenport renovated farmhouse is a charming retreat located just 6.6 km from Shelter Island Whale's Tail, with a perfect review rating of 10. This family-friendly hotel features a full kitchen equipped with modern appliances, perfect for preparing meals, and a lovely patio for relaxation. Guests can enjoy nearby paddleboating, kayaking, and even a marina, making it a great choice for outdoor enthusiasts.American Beech - Luxury 2 Bedroom Apartment 10American Beech - Luxury 2 Bedroom Apartment 10 is conveniently located 5.6 km from Shelter Island Whale's Tail, with an outstanding travellers' rating of 10. This luxurious apartment offers a free breakfast to start the day, along with a cozy fireplace and a spacious patio for family gatherings. It's an ideal romantic getaway, ensuring travellers enjoy both comfort and convenience.Fordham HouseFordham House, a delightful 3-star hotel situated 6.3 km from Shelter Island Whale's Tail, has received an impressive review rating of 10 from travellers. Guests will appreciate the complimentary weekend breakfast and free WiFi access, along with self-parking options. The hotel features premium bedding for a restful night, and the nearby beach adds an extra layer of charm for those looking to unwind by the water.

What are the best boutique hotels near Shelter Island Whale's Tail?

For travellers seeking a boutique hotel experience near Shelter Island Whale's Tail, there are charming options that offer both style and comfort.Zey HotelZey Hotel is a delightful 3.5-star boutique hotel located just 5.6 km from Shelter Island Whale's Tail, with an impressive review rating of 9.2. This adults-only retreat features a serene terrace, perfect for unwinding, along with complimentary breakfast offerings to start the day right. Guests will appreciate the nearby beach access, and the convenience of free onsite parking and bicycles for exploring the area. Enjoy the comfort of premium bedding and a minibar in each room, ensuring a cozy stay at this stylish hotel.

Are there any hotels with pools close to Shelter Island Whale's Tail?

If you're seeking a refreshing stay at hotels with pools near Shelter Island Whale's Tail, look no further. Here are some top-rated options that offer great amenities for a relaxing getaway.The Pridwin HotelThe Pridwin Hotel, located only 4.0 km from Shelter Island Whale's Tail, is a charming 4-star hotel with an impressive review rating of 9.4. Guests can unwind at the beautiful poolside bar while enjoying the scenic views. The hotel offers complimentary breakfast daily, a serene spa with hydrotherapy treatments, and beach access, making it a perfect spot for families looking for a relaxing retreat.The Harbor Front InnThe Harbor Front Inn is a cozy 3.5-star hotel just 5.1 km from Shelter Island Whale's Tail, highly rated with a review score of 8.8. This hotel features a lovely pool with sun loungers, perfect for a leisurely afternoon. Guests can enjoy free breakfast, designer toiletries, and access to a nearby beach. The hotel's family-friendly amenities, including free cribs and connecting rooms, make it a fantastic choice for travellers with children.Greenporter HotelGreenporter Hotel is situated just 5.1 km from Shelter Island Whale's Tail and boasts a stellar review rating of 9.2. Guests can enjoy a shared pool complete with sun loungers and umbrellas, perfect for soaking up the sun. The hotel also features accessibility options for the pool, Egyptian cotton sheets for a comfortable sleep, and a fitness centre. With nearby winery tours and an inviting garden, this hotel offers a delightful blend of relaxation and adventure.

What are the best pet-friendly hotels near Shelter Island Whale's Tail?

For travellers looking for pet-friendly accommodations near Shelter Island Whale's Tail, these top-rated hotels offer a perfect blend of comfort and welcoming amenities for both travellers and their furry friends.The Harbor Front InnThe Harbor Front Inn is a charming 3.5-star hotel located just 5.1 km from Shelter Island Whale's Tail, with a great traveler rating score of 8.8. This hotel is ideal for pet owners, allowing dogs and providing convenient amenities such as pet-friendly rooms and beach towels. Guests can enjoy a refreshing dip in the pool or relax on the terrace. Additional features include free breakfast, air conditioning, and designer toiletries, ensuring a delightful stay.American Beech HotelAmerican Beech Hotel, a stylish 3.5-star hotel situated 5.6 km from Shelter Island Whale's Tail, boasts an impressive travellers' rating of 8.8. This hotel is perfect for travellers with pets, offering amenities like food and water bowls for your furry companions. Guests can indulge in a free daily breakfast, explore the nearby beach, or take advantage of complimentary bicycles for local adventures. With comfortable rooms featuring premium bedding and air conditioning, this hotel promises a cozy retreat.The Rams Head InnThe Rams Head Inn is a delightful 4-star hotel located merely 5.0 km from Shelter Island Whale's Tail, rated 7.6 by travellers. This hotel offers a warm welcome to pets, featuring pet-friendly accommodations and a private beach access. Guests can enjoy complimentary breakfast, yoga classes, and romantic dining options. With amenities like premium bedding and a garden, this inn combines relaxation and charm, making it an excellent choice for pet-friendly travel.

Can I book a fully refundable hotel close to Shelter Island Whale's Tail?

Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Shelter Island Whale's Tail", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

Search Hotels Near Shelter Island Whale's Tail, Shelter Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Shelter Island Whale's Tail hotels

1. House on Chase Creek

2. The Chequit

3. Shelter Island House

4. West Neck Guesthouse

5. The Roundtree, Amagansett

6. The Menhaden

7. The 1770 House Restaurant & Inn

8. North Fork Resort

9. East Hampton Art House Bed & Breakfast

10. The Hedges Inn

11. The Shoals Suites and Slips

12. Zey Hotel

13. The Pridwin Hotel

14. Journey East Hampton

15. Oyster Estate

16. A Room At The Beach

17. East Hampton House Resort

18. Cliffside Resort Condominiums

19. The Huntting Inn

20. Topping Rose House

Compare popular hotels close to Shelter Island Whale's Tail

Top Shelter Island Whale's Tail Hotel Reviews

Bright and Spacious Summer Home Steps from the Beach

Shelter Island House

Zey Hotel

Waterfront House With Dock And Private Beach

Huge Island Getaway Pool Hot Tub Walk To Beach

Work and Play Special! Extended Stay Discount

House on Chase Creek

Other attractions near Shelter Island Whale's Tail

Wades Beach

Sylvester Manor

Shelter Island Historical Society

Havens House

Gardiner's Bay Country Club

Menhadden Lane Beach

Mashomack Preserve

Shelter Island Country Club

Frequently asked questions