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

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Check prices for these dates

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10 Dec - 11 Dec
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11 Dec - 12 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Our top choices for Shelter Island Whale's Tail hotels

Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
4.2 km from Shelter Island Whale's Tail
9.8 out of 10, Exceptional, (141)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Property entrance
The Menhaden

The Menhaden

The Menhaden
3.5 star property
3.8 km from Shelter Island Whale's Tail
9.6 out of 10, Exceptional, (171)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
United States
Cory
The price is Rp3.556.657
Rp4.730.481 total
includes taxes & fees
24 Dec - 25 Dec
The Menhaden
Exterior
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
6 km from Shelter Island Whale's Tail
9.6 out of 10, Exceptional, (227)
"Food!"
United States
Ryan
The price is Rp3.093.232
Rp3.534.018 total
includes taxes & fees
14 Dec - 15 Dec
The Shoals Suites and Slips
Beach nearby, white sand, sun-loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
19.5 km from Shelter Island Whale's Tail
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is Rp9.911.802
Rp11.890.383 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Roundtree, Amagansett
Building design
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
8.8 km from Shelter Island Whale's Tail
9.4 out of 10, Exceptional, (573)
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is Rp3.585.340
Rp4.096.251 total
includes taxes & fees
14 Dec - 15 Dec
Sag Harbor Inn
Exterior
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
3.9 km from Shelter Island Whale's Tail
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
Aerial view
East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
14.7 km from Shelter Island Whale's Tail
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
The price is Rp6.555.169
Rp7.489.192 total
includes taxes & fees
15 Dec - 16 Dec
East Hampton Art House Bed & Breakfast
Lobby lounge
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
3.8 km from Shelter Island Whale's Tail
8.8 out of 10, Excellent, (545)
"Awesome stay!!! Great Location "
United States
Bryan
The price is Rp2.186.557
Rp3.314.264 total
includes taxes & fees
24 Dec - 25 Dec
The Harbor Front Inn
Bar (on property)
Bridgehampton Inn

Bridgehampton Inn

Bridgehampton Inn
3.5 star property
15.9 km from Shelter Island Whale's Tail
9.4 out of 10, Exceptional, (218)
"Great place!!!"
United States
Leslie
The price is Rp4.986.124
Rp5.696.688 total
includes taxes & fees
15 Dec - 16 Dec
Bridgehampton Inn
Outdoor pool
Topping Rose House

Topping Rose House

Topping Rose House
4.5 star property
15.6 km from Shelter Island Whale's Tail
9.2 out of 10, Wonderful, (136)
"Great rooms, staff and food"
United Kingdom
Alexandra
The price is Rp8.929.998
Rp10.260.890 total
includes taxes & fees
12 Dec - 13 Dec
Topping Rose House
Resort view
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
5.9 km from Shelter Island Whale's Tail
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is Rp2.820.745
Rp4.038.825 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sound View Greenport
Beach nearby
The Huntting Inn

The Huntting Inn

The Huntting Inn
3.5 star property
17.7 km from Shelter Island Whale's Tail
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is Rp6.378.570
Rp7.454.172 total
includes taxes & fees
24 Dec - 25 Dec
The Huntting Inn
Front of property – evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
17.4 km from Shelter Island Whale's Tail
9.0 out of 10, Wonderful, (73)
"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...
United States
margaret
The price is Rp5.002.800
Rp6.287.352 total
includes taxes & fees
14 Dec - 15 Dec
Mill House Inn
View from property
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
18.8 km from Shelter Island Whale's Tail
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Property entrance
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
15.8 km from Shelter Island Whale's Tail
8.8 out of 10, Excellent, (211)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is Rp2.536.420
Rp3.564.691 total
includes taxes & fees
22 Dec - 23 Dec
The Sagaponack
Property entrance
The Maidstone

The Maidstone

The Maidstone
4.0 star property
17.8 km from Shelter Island Whale's Tail
8.0 out of 10, Very good, (150)
"We had a wonderful stay "
United States
Sabrina
The price is Rp5.598.967
Rp6.396.820 total
includes taxes & fees
14 Dec - 15 Dec
The Maidstone
Traditional Cottage, 2 Bedrooms, Lake View | Desk, laptop workspace, iron/ironing board, free WiFi
Head of Pond House

Head of Pond House

Head of Pond House
3.0 star property
18 km from Shelter Island Whale's Tail
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is Rp8.254.620
Rp9.430.903 total
includes taxes & fees
5 Jan - 6 Jan 2026
Head of Pond House
Exterior
Wainscott Woods Retreat

Wainscott Woods Retreat

Wainscott Woods Retreat
2.5 star property
15.8 km from Shelter Island Whale's Tail
7.0 out of 10, Good, (9)
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
The price is Rp3.760.938
Rp4.296.872 total
includes taxes & fees
7 Jan - 8 Jan 2026
Wainscott Woods Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelter Island Whale's Tail Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Always love staying there when in Greenport. Clean. Central. Quality continental breakfast."
Carmela 2-night trip
Posted 2 weeks ago
The Harbor Front Inn

Hotels near other Shelter Island Whale's Tail attractions

Wades Beach

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

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

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 22 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 Harbor Front Inn is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and a 24-hour fitness centre. It's located 2.3 mi (3.8 km) from Shelter Island Whale's Tail. Other good options within 5 miles include Sound View Greenport and The Chequit.
How many hotels are there near Shelter Island Whale's Tail?
Expedia has 22 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 Railroad Museum of Long Island, East End Seaport Maritime Museum 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.