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29 Sep - 30 Sep
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30 Sep - 1 Oct
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2 Oct - 4 Oct
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9 Oct - 11 Oct

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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 serene lakeside view with two Adirondack chairs facing a calm lake, surrounded by trees and a clear sky.
A sign for 'House on Chase Creek' with a duck illustration.

1. House on Chase Creek

House on Chase Creek
1.9 km from Shelter Island Whale's Tail
United States
Calvin
฿7,188
฿8,212 total
includes taxes & fees
12 Oct - 13 Oct
House on Chase Creek
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 staircase with wooden balusters and a white wall.
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

2. The Chequit

The Chequit
2.1 km from Shelter Island Whale's Tail
United States
Kristin
฿6,911
฿7,896 total
includes taxes & fees
4 Oct - 5 Oct
The Chequit
Front of property – evening/night
Bar (on property)
Property amenity
Terrace/patio

3. Shelter Island House

Shelter Island House
2.4 km from Shelter Island Whale's Tail
United States
Dorothy
฿6,719
฿7,676 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
A grassy area with trees and a view of a body of water.
A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.2 km from Shelter Island Whale's Tail
United States
Keith
฿10,851
฿12,397 total
includes taxes & fees
12 Oct - 13 Oct
Silver Sands Motel & Beach Bungalows
A beach chair with a striped cushion and a bag with a floral design.
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.
A room with a bookshelf, a chair, a lamp, and a wall mural depicting a beach scene.

5. The Hedges Inn

The Hedges Inn
18 km from Shelter Island Whale's Tail
United States
Lauren
฿13,328
฿17,198 total
includes taxes & fees
25 Oct - 26 Oct
The Hedges Inn
An outdoor dining area with trees and tables under string lights.
A white house with a sign reading "The 1770 House Restaurant & Inn."
A restaurant with wooden beams, tables with white tablecloths, and a bar area.
A garden pathway leading to a white picket fence and a building with an American flag.

6. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
17.7 km from Shelter Island Whale's Tail
United States
Lisa
฿15,166
฿20,733 total
includes taxes & fees
19 Oct - 20 Oct
The 1770 House Restaurant & Inn
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 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 modern bedroom with a bed, a desk with a chair, a television, and a large mirror.

7. The Roundtree, Amagansett

The Roundtree, Amagansett
19.5 km from Shelter Island Whale's Tail
United States
Ryan
฿23,180
฿27,807 total
includes taxes & fees
1 Oct - 2 Oct
The Roundtree, Amagansett
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 modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.
A tented accommodation with a bed, television, and a small table with a chair.

8. North Fork Resort

North Fork Resort
5.1 km from Shelter Island Whale's Tail
United States
Harold
฿9,883
฿11,291 total
includes taxes & fees
30 Sept - 1 Oct
North Fork Resort
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.
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.
A beach with a lifeguard tower, a few people sitting on chairs, and a white umbrella.

9. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
14.7 km from Shelter Island Whale's Tail
United States
IVAN
฿22,861
฿26,119 total
includes taxes & fees
1 Oct - 2 Oct
East Hampton Art House Bed & Breakfast
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 rooftop deck with outdoor seating, fire pits, and a view of a body of water.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

10. The Menhaden

The Menhaden
3.8 km from Shelter Island Whale's Tail
United States
Lisa
฿10,616
฿13,473 total
includes taxes & fees
30 Sept - 1 Oct
The Menhaden
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 storefront with a sign reading "THE SHOALS".
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

11. The Shoals Suites and Slips

The Shoals Suites and Slips
6 km from Shelter Island Whale's Tail
United States
Melissa
฿6,782
฿8,588 total
includes taxes & fees
1 Oct - 2 Oct
The Shoals Suites and Slips
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

12. Sag Harbor Inn

Sag Harbor Inn
8.8 km from Shelter Island Whale's Tail
United States
Terri
฿8,367
฿9,559 total
includes taxes & fees
30 Oct - 31 Oct
Sag Harbor Inn
A dining area with a fireplace, bookshelves, and a view of the bar area.
A two-story building with a brick pathway leading to the entrance.
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.

13. Bridgehampton Inn

Bridgehampton Inn
15.9 km from Shelter Island Whale's Tail
United States
Leslie
฿9,983
฿11,405 total
includes taxes & fees
12 Oct - 13 Oct
Bridgehampton Inn
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A restaurant with a signboard listing its hours of operation.
A bar area with stools, a shelf with glasses, and decorative plants.
A bathroom with a bathtub, green tiled walls, and windows with white blinds.

14. Zey Hotel

Zey Hotel
3.9 km from Shelter Island Whale's Tail
United States
Renee
฿5,671
฿6,479 total
includes taxes & fees
4 Oct - 5 Oct
Zey Hotel
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 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.

15. Journey East Hampton

Journey East Hampton
18.8 km from Shelter Island Whale's Tail
United States
NAKUL
฿8,372
฿10,521 total
includes taxes & fees
12 Oct - 13 Oct
Journey East Hampton
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.
A bathtub surrounded by candles and flower petals.
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

A Room At The Beach
15.5 km from Shelter Island Whale's Tail
United States
Barbara
฿9,886
฿11,294 total
includes taxes & fees
4 Oct - 5 Oct
A Room At The Beach
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A wooden reception desk with a notepad, a vase with dried flowers, and various decorative items on shelves above.
A poolside area with lounge chairs and yellow umbrellas.
A sign for Oyster Estate with a tree in the background.

17. Oyster Estate

Oyster Estate
3.9 km from Shelter Island Whale's Tail
United States
Elizabeth
฿10,081
฿12,701 total
includes taxes & fees
20 Oct - 21 Oct
Oyster Estate
Living area
Front of property
Reception
Room

18. East Hampton House Resort

East Hampton House Resort
18.3 km from Shelter Island Whale's Tail
United States
James
฿5,141
฿6,787 total
includes taxes & fees
28 Oct - 29 Oct
East Hampton House Resort
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A vase with flowers and a bowl on a dresser against a wall.
A large building with multiple floors, surrounded by a residential area with houses and a body of water.

19. The Harbor Front Inn

The Harbor Front Inn
3.8 km from Shelter Island Whale's Tail
United States
Jordan
฿7,530
฿9,563 total
includes taxes & fees
25 Oct - 26 Oct
The Harbor Front Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A spacious living room with a fireplace, comfortable seating, and large windows.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

20. Faraway Sag Harbor

Faraway Sag Harbor
8.9 km from Shelter Island Whale's Tail
United States
Miguel
฿14,214
฿17,864 total
includes taxes & fees
5 Oct - 6 Oct
Faraway Sag Harbor
View all properties

Compare popular hotels close to Shelter Island Whale's Tail

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A serene landscape with a calm body of water reflecting trees with autumn foliage.
House on Chase Creek
9.4
Exceptional
86 reviews
View
An outdoor patio area with string lights, tables, chairs, and a fire pit.
The Chequit
9.2
Wonderful
64 reviews
View
Front of property – evening/night
Shelter Island House
8.4
Very good
66 reviews
View
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
Silver Sands Motel & Beach Bungalows
10.0
Exceptional
171 reviews
View
A beach chair with a striped cushion and a bag with a floral design.
The Hedges Inn
9.8
Exceptional
82 reviews
View

Top Shelter Island Whale's Tail Hotel Reviews

North Fork Resort

North Fork Resort

10/10 Excellent
"Fantastic contemporary cottage. Looks brand new and it has everything. Wonderful place to stay. Check in process needs improvement with more attention paid to details by staff."
marie 1-night trip
Posted less than an hour ago
North Fork Resort
Zey Hotel

Zey Hotel

10/10 Excellent
"Adorable, comfy, clean , and convenient with friendly staff."
Nina 2-night trip
Posted 6 hours ago
Zey Hotel
The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"The hotel was just what we expected, cozy and comfortable and nestled right into central Greenport. Close to everything, dinner spots just steps away. Will definitely return."
Arnold 2-night trip
Posted 19 hours ago
The Harbor Front Inn
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

10/10 Excellent
"This is a great place that brings you back to a special time. Staff were exceptionally friendly and helpful. Made us feel like we were family - highly recommend."
Keith 3-night trip
Posted 23 hours ago
Silver Sands Motel & Beach Bungalows
The Chequit

The Chequit

8/10 Good
"The only real problem was the constant loud noise of air rushing outside the room from an air shaft along side the chimney. The staff was not able to quiet it. Most of the noise came in via the window a/c unit so removing it and closing the window would have helped. There refrigerator was warm when we arrived but, the evening clerk promptly got it running for us."
Peter 1-night trip
Posted 2 days ago
The Chequit
The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"This place is awesome! It is very well appointed and very comfortable beds. It's a beautiful space with lots of outdoor space and lovely views of the small marina next door. We were in town for just one night, wish we could have stayed longer. I'd go back in a heartbeat!"
Susan 1-night trip
Posted 7 days ago
The Shoals Suites and Slips
Oyster Estate

Oyster Estate

10/10 Excellent
"Newly renovated. Place looks great."
john 2-night trip
Posted 9 days ago
Oyster Estate
American Beech Hotel

American Beech Hotel

10/10 Excellent
"Fun picnic breakfast left at the door at 9am"
Peter 1-night trip
Posted 13 days ago
American Beech Hotel
Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

10/10 Excellent
"Clean room, breakfasts were delightful and great location."
James 4-night trip
Posted 1 month ago
Stirling House Bed & Breakfast

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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?
See properties

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.
See properties

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 20 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 Zey Hotel and The Harbor Front Inn.
How many hotels are there near Shelter Island Whale's Tail?
Expedia has 20 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, 67 Steps Beach and Crescent Beach.