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Search Guest Houses in Shelter Island

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Check prices for these dates

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

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

2.5 star property
9.4 out of 10, Exceptional, (67)
"Everything you need for a stay on the island"
The price is SAR 391
SAR 446 total
includes taxes & fees
3 Mar - 4 Mar
House on Chase Creek

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 SAR 731
SAR 1,563 total
includes taxes & fees
24 Feb - 25 Feb
New and Modern Bridgehampton Accommodations

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (4)
"Nice"
The price is SAR 521
SAR 831 total
includes taxes & fees
23 Feb - 24 Feb
Aqua by American Beech - Superior King

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is SAR 671
SAR 1,010 total
includes taxes & fees
23 Feb - 24 Feb
American Beech in Greenport NY - King Suite 1

American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3

American Beech in Greenport - Two-Bedroom Apartment 8

The price is SAR 1,159
SAR 1,656 total
includes taxes & fees
28 Feb - 1 Mar
American Beech in Greenport - Two-Bedroom Apartment 8

Aqua by American Beech - Deluxe King

8.0 out of 10, Very Good, (1)
The price is SAR 559
SAR 878 total
includes taxes & fees
23 Feb - 24 Feb
Aqua by American Beech - Deluxe King

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 SAR 671
SAR 1,002 total
includes taxes & fees
23 Feb - 24 Feb
American Beech - King Suite 2

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
The price is SAR 971
SAR 1,390 total
includes taxes & fees
14 Mar - 15 Mar
American Beech - Deluxe King Suite 14

American Beech in Greenport - Deluxe King Suite 12

The price is SAR 896
SAR 1,293 total
includes taxes & fees
7 Mar - 8 Mar
American Beech in Greenport - Deluxe King Suite 12

American Beech in Greenport - Deluxe King Suite 11

The price is SAR 896
SAR 1,293 total
includes taxes & fees
7 Mar - 8 Mar
American Beech in Greenport - Deluxe King Suite 11

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

Aqua by American Beech - Superior with 2 Queens

Victorian Seasons Stirling

3.5 star property
Victorian Seasons Stirling

The North Fork Loft

The North Fork Loft

Aqua by American Beech - Deluxe with 2 Queen

Aqua by American Beech - Deluxe with 2 Queen

Ruschmeyers #14 - Dlx Queen

2.5 star property
Ruschmeyers #14 - Dlx Queen

Ruschmeyers #5 - Queen

2.5 star property
Ruschmeyers #5 - Queen

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

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 SAR 491
SAR 634 total
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor

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 SAR 421
SAR 518 total
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites

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 SAR 494
SAR 645 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.