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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Shelter Island Guest Houses

Steps from the Ocean
On the beach, sun loungers, beach towels

Steps from the Ocean

10.0 out of 10, Exceptional, (53)
"We had a wonderful time and enjoyed this beautiful home in the off season which was perfect for the chill getaway we were looking for!"
Steps from the Ocean
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (67)
"Everything you need for a stay on the island"
The price is CA $150
CA $171 total
includes taxes & fees
Feb 3 - Feb 4
House on Chase Creek
New and Modern Bridgehampton Accommodations
Outdoor pool, a heated pool

New and Modern Bridgehampton Accommodations

2.0 star property
10.0 out of 10, Exceptional, (8)
"the perfect weekend getaway! if you are looking for somewhere relaxing to stay nearby beaches & shops in the hamptons this is the place to stay! the property itself was beautiful with many great features to enjoy inside and outside. was very secluded and private as well which we enjoyed. the apartment was clean, and the check-in & out process was seamless. definitely reccomend! "
The price is CA $281
CA $599 total
includes taxes & fees
Feb 2 - Feb 3
New and Modern Bridgehampton Accommodations
Aqua by American Beech - Superior King
Property grounds

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (4)
"Nice"
The price is CA $243
CA $374 total
includes taxes & fees
Jan 31 - Feb 1
Aqua by American Beech - Superior King
American Beech in Greenport NY - King Suite 1
Interior

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is CA $258
CA $392 total
includes taxes & fees
Feb 2 - Feb 3
American Beech in Greenport NY - King Suite 1
American Beech in Greenport - King Suite 3
Property grounds

American Beech in Greenport - King Suite 3

The price is CA $258
CA $392 total
includes taxes & fees
Feb 2 - Feb 3
American Beech in Greenport - King Suite 3
American Beech in Greenport - Two-Bedroom Apartment 8
Interior

American Beech in Greenport - Two-Bedroom Apartment 8

The price is CA $445
CA $636 total
includes taxes & fees
Feb 21 - Feb 22
American Beech in Greenport - Two-Bedroom Apartment 8
Aqua by American Beech - Deluxe King
Terrace/patio

Aqua by American Beech - Deluxe King

8.0 out of 10, Very good, (1)
The price is CA $272
CA $410 total
includes taxes & fees
Jan 31 - Feb 1
Aqua by American Beech - Deluxe King
American Beech - King Suite 2
Interior

American Beech - King Suite 2

10.0 out of 10, Exceptional, (1)
"Wonderful weekend getaway. American Beech offers a perfect blend of privacy and indulgence. Great communication, cool vibe, and a variety of fun food and drink options."
The price is CA $258
CA $395 total
includes taxes & fees
Feb 2 - Feb 3
American Beech - King Suite 2
American Beech - Deluxe King Suite 14
Interior

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
The price is CA $315
CA $465 total
includes taxes & fees
Jan 31 - Feb 1
American Beech - Deluxe King Suite 14
American Beech in Greenport - Deluxe King Suite 12
Interior

American Beech in Greenport - Deluxe King Suite 12

The price is CA $344
CA $502 total
includes taxes & fees
Feb 7 - Feb 8
American Beech in Greenport - Deluxe King Suite 12
American Beech in Greenport - Deluxe King Suite 11
Interior

American Beech in Greenport - Deluxe King Suite 11

The price is CA $344
CA $502 total
includes taxes & fees
Feb 7 - Feb 8
American Beech in Greenport - Deluxe King Suite 11
Hampton's Vacation Inn
Apartment, 2 Bedrooms | Private kitchen

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (272)
"Very clean and quiet."
Hampton's Vacation Inn
Aqua by American Beech - Superior with 2 Queens
Outdoor dining

Aqua by American Beech - Superior with 2 Queens

Aqua by American Beech - Superior with 2 Queens
Victorian Seasons Stirling
Romantic House, 4 Bedrooms, Kitchen, Garden View | Terrace/patio

Victorian Seasons Stirling

3.5 star property
Victorian Seasons Stirling
The North Fork Loft
Interior

The North Fork Loft

The North Fork Loft
Aqua by American Beech - Deluxe with 2 Queen
Property grounds

Aqua by American Beech - Deluxe with 2 Queen

Aqua by American Beech - Deluxe with 2 Queen
Ruschmeyers #14 - Dlx Queen
House, 1 Queen Bed (Ruschmeyers #14 - Dlx Queen) | Exterior

Ruschmeyers #14 - Dlx Queen

2.5 star property
Ruschmeyers #14 - Dlx Queen
Ruschmeyers #5 - Queen
House, 1 Queen Bed (Ruschmeyers #5 - Queen) | Property grounds

Ruschmeyers #5 - Queen

2.5 star property
Ruschmeyers #5 - Queen
Ruschmeyers #11 - Dlx Queen
House, 1 Queen Bed (Ruschmeyers #11 - Dlx Queen) | Exterior

Ruschmeyers #11 - Dlx Queen

2.5 star property
Ruschmeyers #11 - Dlx Queen
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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Other property types in Shelter Island

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1103)
"The King size bed was very nice to sleep on for my back "
The price is CA $189
CA $243 total
includes taxes & fees
Feb 3 - Feb 4
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (359)
"Perfect for a short stay. Very warm, clean and comfortable. Very close to shops and beach. Check in and check out was super easy. Only critique would be that the walls were thin and you could very easily hear the conversation of the guests in the room next door. "
The price is CA $196
CA $238 total
includes taxes & fees
Feb 2 - Feb 3
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (268)
"Was a winter wonderland. Quiet and clean. Staff were very helpful and kind!"
The price is CA $190
CA $248 total
includes taxes & fees
Feb 2 - Feb 3
Windward Shores Ocean Resort
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.