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Chalets in Shelter Island

No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island

Daunt's Albatross Motel

2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (287)
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
Daunt's Albatross Motel

Offshore Residences

4.5 star property
Downtown Montauk
The price is SAR 1,798
SAR 2,483 total
includes taxes & fees
9 Dec - 10 Dec
Offshore Residences

Offshore Montauk

2.0 star property
Montauk
9.4 out of 10, Exceptional, (73)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is SAR 305
SAR 563 total
includes taxes & fees
16 Dec - 17 Dec
Offshore Montauk

Hero Beach Club

4.0 star property
Montauk
9.0 out of 10, Wonderful, (201)
"Great weekend trip "
United States
Timothy
The price is SAR 558
SAR 1,019 total
includes taxes & fees
7 Dec - 8 Dec
Hero Beach Club

Kenny's Tipperary Inn

2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (878)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is SAR 520
SAR 668 total
includes taxes & fees
4 Dec - 5 Dec
Montauk Manor

Gurney's Montauk Resort & Seawater Spa

4.0 star property
Montauk
8.2 out of 10, Very Good, (694)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
The price is SAR 833
SAR 1,136 total
includes taxes & fees
15 Dec - 16 Dec
Gurney's Montauk Resort & Seawater Spa

Stylish Woody Interior 1BR+Loft w/ Beach Access

Amagansett
The price is SAR 2,120
SAR 3,846 total
includes taxes & fees
16 Dec - 17 Dec
Stylish Woody Interior 1BR+Loft w/ Beach Access

The Roundtree, Amagansett

4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is SAR 2,231
SAR 2,677 total
includes taxes & fees
1 Jan - 2 January 2026
The Roundtree, Amagansett

Journey East Hampton

4.0 star property
East Hampton North
9.0 out of 10, Wonderful, (159)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
The price is SAR 696
SAR 875 total
includes taxes & fees
9 Dec - 10 Dec
Journey East Hampton

4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

East Hampton
The price is SAR 3,941
SAR 6,367 total
includes taxes & fees
31 Dec - 1 January 2026
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

Blackberry: Private home with jacuzzi year-round

East Hampton
9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is SAR 281
SAR 3,306 total
includes taxes & fees
4 Dec - 5 Dec
Blackberry: Private home with jacuzzi year-round

The Huntting Inn

3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is SAR 1,436
SAR 1,678 total
includes taxes & fees
16 Dec - 17 Dec
The Huntting Inn

The 1770 House Restaurant & Inn

4.0 star property
East Hampton
9.8 out of 10, Exceptional, (160)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is SAR 996
SAR 1,362 total
includes taxes & fees
4 Dec - 5 Dec
The 1770 House Restaurant & Inn

The Maidstone

4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
The price is SAR 1,008
SAR 1,151 total
includes taxes & fees
2 Jan - 3 January 2026
The Maidstone

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Waterford
10.0 out of 10, Exceptional, (10)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is SAR 358
SAR 1,359 total
includes taxes & fees
4 Dec - 5 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Gorgeous 5-Bedroom House in East Hampton

East Hampton
The price is SAR 8,257
SAR 16,105 total
includes taxes & fees
9 Dec - 10 Dec
Gorgeous 5-Bedroom House in East Hampton

Upscale Hamptons Home: 1 Mi to Sammys Beach!

East Hampton
9.4 out of 10, Exceptional, (3)
"Wonderful property. Lisette was a fantastic host and her home updated and modern. "
United States
Joanna D.
The price is SAR 2,627
SAR 4,652 total
includes taxes & fees
31 Dec - 1 January 2026
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Coastal New England Waterfront Home, Harkness Park, Casinos

Waterford
10.0 out of 10, Exceptional, (126)
"Wonderful location (very close to downtown Niantic); clean, bright, beautiful home; well appointed kitchen overall; loved gate at top of stairs, rail for bottom bunk and high chair since I have a toddler; owner was very responsive, kind and helpful when needed. I would definitely recommend and stay again!"
United States
Anne M.
The price is SAR 1,235
SAR 2,326 total
includes taxes & fees
4 Dec - 5 Dec
Coastal New England Waterfront Home, Harkness Park, Casinos

Wainscott Woods Retreat

2.5 star property
Wainscott
7.0 out of 10, Good, (9)
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
The price is SAR 1,124
SAR 1,284 total
includes taxes & fees
7 Dec - 8 Dec
Wainscott Woods Retreat
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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Top Shelter Island Hotel Reviews