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Search Guest Houses in Shelter Island from CA $173

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Shelter Island Guest Houses

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 King
Property grounds

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (5)
"Very clean, flexible, great communication and exceptional view"
The price is CA $294
CA $439 total
includes taxes & fees
Apr 7 - Apr 8
Aqua by American Beech - Superior King
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (69)
"Beautiful setting and big rooms close to ferry and town center. "
The price is CA $173
CA $198 total
includes taxes & fees
Apr 7 - Apr 8
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 $317
CA $692 total
includes taxes & fees
Apr 8 - Apr 9
New and Modern Bridgehampton Accommodations
Steps from the Ocean
On the beach, sun loungers, beach towels

Steps from the Ocean

10.0 out of 10, Exceptional, (54)
"Really enjoyed our two nights away with the family. Great way to unplug and enjoy nature!"
Steps from the Ocean
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 $252
CA $384 total
includes taxes & fees
Apr 7 - Apr 8
American Beech in Greenport NY - King Suite 1
American Beech - King Suite 2
Interior

American Beech - King Suite 2

10.0 out of 10, Exceptional, (2)
"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 $252
CA $381 total
includes taxes & fees
Apr 7 - Apr 8
American Beech - King Suite 2
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 $322
CA $474 total
includes taxes & fees
Apr 8 - Apr 9
Aqua by American Beech - Deluxe King
American Beech in Greenport - Two-Bedroom Apartment 8
Interior

American Beech in Greenport - Two-Bedroom Apartment 8

The price is CA $435
CA $632 total
includes taxes & fees
Apr 6 - Apr 7
American Beech in Greenport - Two-Bedroom Apartment 8
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 $336
CA $494 total
includes taxes & fees
Apr 6 - Apr 7
American Beech - Deluxe King Suite 14
American Beech in Greenport - King Suite 3
Property grounds

American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3
American Beech in Greenport - Deluxe King Suite 11
Interior

American Beech in Greenport - Deluxe King Suite 11

The price is CA $308
CA $457 total
includes taxes & fees
Apr 7 - Apr 8
American Beech in Greenport - Deluxe King Suite 11
American Beech in Greenport - Deluxe King Suite 12
Interior

American Beech in Greenport - Deluxe King Suite 12

The price is CA $308
CA $457 total
includes taxes & fees
Apr 7 - Apr 8
American Beech in Greenport - Deluxe King Suite 12
Victorian Seasons Stirling
Romantic House, 4 Bedrooms, Kitchen, Garden View | Terrace/patio

Victorian Seasons Stirling

3.5 star property
Victorian Seasons Stirling
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
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
The North Fork Loft
Interior

The North Fork Loft

The North Fork Loft
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

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
The price is CA $1,138
CA $2,039 total
includes taxes & fees
Apr 30 - May 1
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1149)
"the location is great and price is reasonable. "
The price is CA $209
CA $266 total
includes taxes & fees
Apr 21 - Apr 22
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (368)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is CA $192
CA $234 total
includes taxes & fees
Apr 9 - Apr 10
Montauk Oceanside Suites
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.