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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 17 Guest Houses in Shelter Island with updated reviews, rates, and availability.

Hampton's Vacation Inn
Apartment, 2 Bedrooms | Private kitchen | Microwave, coffee/tea maker, highchair, cookware/dishes/utensils

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 AED 768
AED 1,145 total
includes taxes & fees
15 Apr - 16 Apr
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 AED 451
AED 516 total
includes taxes & fees
14 Apr - 15 Apr
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 AED 826
AED 1,838 total
includes taxes & fees
14 Apr - 15 Apr
New and Modern Bridgehampton Accommodations
Steps from the Ocean
Smart TV, fireplace, books

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
1 bedroom, iron/ironing board, internet

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is AED 804
AED 1,196 total
includes taxes & fees
13 Apr - 14 Apr
American Beech in Greenport NY - King Suite 1
American Beech - King Suite 2
Exterior

American Beech - King Suite 2

10.0 out of 10, Exceptional, (2)
"Excellent one night stay."
The price is AED 804
AED 1,221 total
includes taxes & fees
14 Apr - 15 Apr
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 AED 841
AED 1,224 total
includes taxes & fees
20 Apr - 21 Apr
Aqua by American Beech - Deluxe King
American Beech in Greenport - Two-Bedroom Apartment 8
TV, fireplace

American Beech in Greenport - Two-Bedroom Apartment 8

The price is AED 1,135
AED 1,649 total
includes taxes & fees
13 Apr - 14 Apr
American Beech in Greenport - Two-Bedroom Apartment 8
American Beech - Deluxe King Suite 14
1 bedroom, iron/ironing board, internet, bed sheets

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
The price is AED 988
AED 1,393 total
includes taxes & fees
20 Apr - 21 Apr
American Beech - Deluxe King Suite 14
American Beech in Greenport - King Suite 3
Lobby

American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3
American Beech in Greenport - Deluxe King Suite 11
1 bedroom, iron/ironing board, internet, bed sheets

American Beech in Greenport - Deluxe King Suite 11

The price is AED 878
AED 1,309 total
includes taxes & fees
15 Apr - 16 Apr
American Beech in Greenport - Deluxe King Suite 11
American Beech in Greenport - Deluxe King Suite 12
1 bedroom, iron/ironing board, internet, bed sheets

American Beech in Greenport - Deluxe King Suite 12

The price is AED 878
AED 1,309 total
includes taxes & fees
15 Apr - 16 Apr
American Beech in Greenport - Deluxe King Suite 12
Victorian Seasons Stirling
Exterior detail

Victorian Seasons Stirling

3.5 star property
Victorian Seasons Stirling
Aqua by American Beech - Superior with 2 Queens
Terrace/patio

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 AED 2,938
AED 5,267 total
includes taxes & fees
30 Apr - 1 May
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, (1152)
"Wonderful experience. The only problem was the jacuzzi was only working the first 2 days of my stay"
The price is AED 545
AED 695 total
includes taxes & fees
28 Apr - 29 Apr
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (369)
"We stayed for a night and it was great. It was great location and setting. Overall stay was fantastic. Bathtub was a bit old, could not hold the water and if you are more than 1 person, you have to space your baths so you can all enjoy warm water. "
The price is AED 500
AED 611 total
includes taxes & fees
13 Apr - 14 Apr
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.