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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 20 Guest Houses in Shelter Island with updated reviews, rates, and availability.

Steps from the Ocean
porch view

Steps from the Ocean

10.0 out of 10, Exceptional, (54)
"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
Front of 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 AED 382
AED 437 total
includes taxes & fees
3 Mar - 4 Mar
House on Chase Creek
New and Modern Bridgehampton Accommodations
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 AED 716
AED 1,531 total
includes taxes & fees
24 Feb - 25 Feb
New and Modern Bridgehampton Accommodations
Aqua by American Beech - Superior King
Room

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (4)
"Nice"
The price is AED 511
AED 814 total
includes taxes & fees
23 Feb - 24 Feb
Aqua by American Beech - Superior King
American Beech in Greenport NY - King Suite 1
Room

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is AED 657
AED 989 total
includes taxes & fees
23 Feb - 24 Feb
American Beech in Greenport NY - King Suite 1
American Beech in Greenport - King Suite 3
Room

American Beech in Greenport - King Suite 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 AED 1,135
AED 1,622 total
includes taxes & fees
28 Feb - 1 Mar
American Beech in Greenport - Two-Bedroom Apartment 8
Aqua by American Beech - Deluxe King
Room

Aqua by American Beech - Deluxe King

8.0 out of 10, Very Good, (1)
The price is AED 547
AED 859 total
includes taxes & fees
23 Feb - 24 Feb
Aqua by American Beech - Deluxe King
American Beech - King Suite 2
Room

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 AED 657
AED 982 total
includes taxes & fees
23 Feb - 24 Feb
American Beech - King Suite 2
American Beech - Deluxe King Suite 14
Room

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
The price is AED 951
AED 1,361 total
includes taxes & fees
14 Mar - 15 Mar
American Beech - Deluxe King Suite 14
American Beech in Greenport - Deluxe King Suite 12
Room

American Beech in Greenport - Deluxe King Suite 12

The price is AED 878
AED 1,266 total
includes taxes & fees
7 Mar - 8 Mar
American Beech in Greenport - Deluxe King Suite 12
American Beech in Greenport - Deluxe King Suite 11
Room

American Beech in Greenport - Deluxe King Suite 11

The price is AED 878
AED 1,266 total
includes taxes & fees
7 Mar - 8 Mar
American Beech in Greenport - Deluxe King Suite 11
Hampton's Vacation Inn
Front of property

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
Room

Aqua by American Beech - Superior with 2 Queens

Aqua by American Beech - Superior with 2 Queens
Victorian Seasons Stirling
Exterior detail

Victorian Seasons Stirling

3.5 star property
Victorian Seasons Stirling
The North Fork Loft
Pool

The North Fork Loft

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

Aqua by American Beech - Deluxe with 2 Queen

Aqua by American Beech - Deluxe with 2 Queen
Ruschmeyers #14 - Dlx Queen
Property grounds

Ruschmeyers #14 - Dlx Queen

2.5 star property
Ruschmeyers #14 - Dlx Queen
Ruschmeyers #5 - Queen
Room

Ruschmeyers #5 - Queen

2.5 star property
Ruschmeyers #5 - Queen
Ruschmeyers #11 - Dlx Queen
Meeting facility

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
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1116)
"We loved the manor, it had great amenities and an excellent experience. highly recommend! "
The price is AED 481
AED 621 total
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AED 412
AED 507 total
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (273)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is AED 484
AED 632 total
includes taxes & fees
20 Mar - 21 Mar
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.