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 house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

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

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

1. House on Chase Creek

1.9 km from Shelter Island Whale's Tail

Calvin

Rp4.347.170

Rp4.966.602 total

includes taxes & fees

8 Sept - 9 Sept

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

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.

A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

2. The Chequit

2.1 km from Shelter Island Whale's Tail

Kathleen

Rp5.175.202

Rp5.912.669 total

includes taxes & fees

8 Sept - 9 Sept

3. Shelter Island House

2.4 km from Shelter Island Whale's Tail

Dorothy

Rp5.595.411

Rp6.392.835 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

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

4. West Neck Guesthouse

2 km from Shelter Island Whale's Tail

Allie

Rp5.546.756

Rp6.337.279 total

includes taxes & fees

1 Sept - 2 Sept

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

A garden pathway leading to a white picket fence and a building with an American flag.

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.

5. The 1770 House Restaurant & Inn

17.7 km from Shelter Island Whale's Tail

Lisa

Rp8.647.454

Rp11.821.578 total

includes taxes & fees

21 Sept - 22 Sept

A beach with waves gently lapping onto the shore.

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.

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.

6. The Roundtree, Amagansett

19.5 km from Shelter Island Whale's Tail

Ryan

Rp12.283.846

Rp14.735.998 total

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 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.

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

7. The Menhaden

3.8 km from Shelter Island Whale's Tail

Lisa

Rp10.295.557

Rp12.470.380 total

includes taxes & fees

1 Sept - 2 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 rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

8. North Fork Resort

5.1 km from Shelter Island Whale's Tail

Lisa

Rp5.684.761

Rp6.494.839 total

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 beach with a lifeguard tower, a few people sitting on chairs, and a white umbrella.

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

9. East Hampton Art House Bed & Breakfast

14.7 km from Shelter Island Whale's Tail

IVAN

Rp12.114.751

Rp13.841.234 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

10. The Hedges Inn

18 km from Shelter Island Whale's Tail

Lauren

Rp9.538.296

Rp11.941.360 total

includes taxes & fees

21 Sept - 22 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 light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

11. The Shoals Suites and Slips

6 km from Shelter Island Whale's Tail

Melissa

Rp4.285.067

Rp5.338.015 total

includes taxes & fees

1 Oct - 2 Oct

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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

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

12. The Pridwin Hotel

3.7 km from Shelter Island Whale's Tail

Anna

Rp9.453.021

Rp11.880.058 total

includes taxes & fees

15 Sept - 16 Sept

A waterfront property with a large house, multiple boats docked, and lush greenery.

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

13. Sag Harbor Inn

8.8 km from Shelter Island Whale's Tail

Loretta

Rp6.263.322

Rp7.155.847 total

includes taxes & fees

20 Sept - 21 Sept

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

A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

14. Zey Hotel

3.9 km from Shelter Island Whale's Tail

shaun

Rp3.582.832

Rp4.093.386 total

includes taxes & fees

1 Sept - 2 Sept

A dining area with a fireplace, bookshelves, and a view of the bar area.

A room with two armchairs, a small table with a vase of flowers, and a patterned rug.

A bedroom with a wooden headboard, a bedside table with a lamp, and a bed with a grey blanket.

An outdoor wedding setup with white chairs, a table with floral arrangements, and a white canopy.

15. Bridgehampton Inn

15.9 km from Shelter Island Whale's Tail

Leslie

Rp5.290.207

Rp6.044.106 total

includes taxes & fees

1 Oct - 2 Oct

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 cozy interior with a wooden bench, a sofa, and a bar area.

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

16. Oyster Estate

3.9 km from Shelter Island Whale's Tail

Jenny

Rp5.759.071

Rp7.256.142 total

includes taxes & fees

7 Sept - 8 Sept

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

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

A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

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

17. Journey East Hampton

18.8 km from Shelter Island Whale's Tail

NAKUL

Rp6.608.336

Rp8.304.985 total

includes taxes & fees

23 Sept - 24 Sept

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

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

A bathtub surrounded by candles and flower petals.

18. A Room At The Beach

15.5 km 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

Rp7.077.200

Rp8.085.701 total

includes taxes & fees

30 Sept - 1 Oct

19. Cliffside Resort Condominiums

5.5 km from Shelter Island Whale's Tail

Christine

Rp5.343.817

Rp7.682.478 total

includes taxes & fees

21 Sept - 22 Sept

A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

An outdoor dining area with tables and chairs, string lights, and hanging lanterns.

A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

20. American Beech Hotel

3.8 km from Shelter Island Whale's Tail

kerri

Rp6.560.564

Rp8.203.006 total

includes taxes & fees

8 Sept - 9 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 64 reviews	View
West Neck Guesthouse	8.2 Very good 46 reviews	View
The 1770 House Restaurant & Inn	9.8 Exceptional 171 reviews	View

Top Shelter Island Whale's Tail Hotel Reviews

The Shoals Suites and Slips

10/10 Excellent

"Loved everything about our stay!"

The Harbor Front Inn

10/10 Excellent

"My family visited this hotel and were very pleased with our decision. Right in the heart of Greenport and minute walk to everything. Will plan to stay here again."

Stirling House Bed & Breakfast

10/10 Excellent

"Clean room, breakfasts were delightful and great location."

The Pridwin Hotel

8/10 Good

"lovely place. Had an issue with my AC and there was nobody around to fix it"

House on Chase Creek

10/10 Excellent

"Nice owner.. convenient location"

Oyster Estate

10/10 Excellent

"Staff looked tired,"

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's the area like around Shelter Island Whale's Tail?

Shelter Island Whale's Tail is located in an area of Shelter Island that travellers like for its island views and beaches. If you're looking for a convenient place to stay, take a look at the 21 hotels and other accommodation options you'll find within a mile.

What's the best hotel to stay near Shelter Island Whale's Tail?

The Chequit is one of the top choices for your stay based on our traveller data, and this hotel offers a restaurant and free parking. It's located 1.3 mi (2.1 km) from Shelter Island Whale's Tail. Other good options within 5 miles include Sound View Greenport and The Pridwin Hotel.

How many hotels are there near Shelter Island Whale's Tail?

Expedia has 21 hotels and other accommodation options within a mile from Shelter Island Whale's Tail.

If I need to cancel the hotel reservation for my stay near Shelter Island Whale's Tail, will I receive a refund?

Yes! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and get a refund within a 24-hour period of your booking. Add dates, click "Search", then you can use the "fully refundable" filter to view the top deals on offer near Shelter Island Whale's Tail.

What can I see and do near Shelter Island Whale's Tail?

You might want to spend some time browsing the exhibits at East End Seaport Maritime Museum, Railroad Museum of Long Island or Havens House. Sights like Greenport Carousel and Sylvester Manor highlight some of the local culture. Dip your toes in the water at Sunset Beach, Crescent Beach and 67 Steps Beach.

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

Change your mind

Treat yourself

Be picky

Check prices for these dates

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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 1770 House Restaurant & Inn

6. The Roundtree, Amagansett

7. The Menhaden

8. North Fork Resort

9. East Hampton Art House Bed & Breakfast

10. The Hedges Inn

11. The Shoals Suites and Slips

12. The Pridwin Hotel

13. Sag Harbor Inn

14. Zey Hotel

15. Bridgehampton Inn

16. Oyster Estate

17. Journey East Hampton

18. A Room At The Beach

19. Cliffside Resort Condominiums

20. American Beech Hotel

Compare popular hotels close to Shelter Island Whale's Tail

Top Shelter Island Whale's Tail Hotel Reviews

The Shoals Suites and Slips

The Harbor Front Inn

Stirling House Bed & Breakfast

The Pridwin Hotel

House on Chase Creek

Oyster Estate

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