Shelter Island Chalets

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Chalets in Shelter Island

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

Recommended hotels in Shelter Island

Outdoor pool, sun loungers
Daunt's Albatross Motel

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
$168 nightly
The price is $192
Dec 17 - Dec 18
Total with taxes and fees
Daunt's Albatross Motel
One Bedroom Condo King with Steam Shower | Terrace/patio
Offshore Residences

Offshore Residences

4.5 star property
Downtown Montauk
$579 nightly
The price is $662
Dec 4 - Dec 5
Total with taxes and fees
Offshore Residences
Ocean View 2 Queens | Premium bedding, pillowtop beds, blackout drapes, free WiFi
Offshore Montauk

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
$131 nightly
The price is $150
Dec 17 - Dec 18
Total with taxes and fees
Offshore Montauk
Hero King Patio Deluxe | Terrace/patio
Hero Beach Club

Hero Beach Club

4.0 star property
Montauk
9.0 out of 10, Wonderful, (201)
"Great weekend trip "
United States
Timothy
$238 nightly
The price is $272
Dec 4 - Dec 5
Total with taxes and fees
Hero Beach Club
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

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
$131 nightly
The price is $150
Dec 17 - Dec 18
Total with taxes and fees
Kenny's Tipperary Inn
Front of property - evening/night
Montauk Manor

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
$156 nightly
The price is $178
Dec 17 - Dec 18
Total with taxes and fees
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

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
$281 nightly
The price is $321
Dec 15 - Dec 16
Total with taxes and fees
Gurney's Montauk Resort & Seawater Spa
Exterior
Stylish Woody Interior 1BR+Loft w/ Beach Access

Stylish Woody Interior 1BR+Loft w/ Beach Access

Amagansett
$911 nightly
The price is $1,021
Dec 9 - Dec 10
Total with taxes and fees
Stylish Woody Interior 1BR+Loft w/ Beach Access
Frette Italian sheets, premium bedding, down comforters
The Roundtree, Amagansett

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
$624 nightly
The price is $713
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Roundtree, Amagansett
Exterior
Journey East Hampton

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
$204 nightly
The price is $233
Dec 9 - Dec 10
Total with taxes and fees
Journey East Hampton
Exterior
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

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

East Hampton
$1,485 nightly
The price is $1,697
Dec 31 - Jan 1, 2026
Total with taxes and fees
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi
Outdoor dining
Blackberry: Private home with jacuzzi year-round

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.
$771 nightly
The price is $881
Dec 4 - Dec 5
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Exterior
The Huntting Inn

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
$393 nightly
The price is $447
Dec 16 - Dec 17
Total with taxes and fees
The Huntting Inn
Garden
The 1770 House Restaurant & 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
$279 nightly
The price is $363
Dec 4 - Dec 5
Total with taxes and fees
The 1770 House Restaurant & Inn
Garden
The Maidstone

The Maidstone

4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
$263 nightly
The price is $301
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Maidstone
Exterior
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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.
$319 nightly
The price is $361
Dec 4 - Dec 5
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Outdoor dining
Gorgeous 5-Bedroom House in East Hampton

Gorgeous 5-Bedroom House in East Hampton

East Hampton
$3,756 nightly
The price is $4,291
Dec 9 - Dec 10
Total with taxes and fees
Gorgeous 5-Bedroom House in East Hampton
Exterior
Upscale Hamptons Home: 1 Mi to Sammys Beach!

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.
$1,085 nightly
The price is $1,240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Upscale Hamptons Home: 1 Mi to Sammys Beach!
Terrace/patio
Coastal New England Waterfront Home, Harkness Park, Casinos

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.
$486 nightly
The price is $550
Dec 7 - Dec 8
Total with taxes and fees
Coastal New England Waterfront Home, Harkness Park, Casinos
Exterior
Wainscott Woods Retreat

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
$299 nightly
The price is $342
Dec 7 - Dec 8
Total with taxes and fees
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Lovely rooms and loved the fireplace. Great stay. Awesome few days away from real life!"
Andrew 2-night trip
Posted 3 days ago
Saybrook Point Resort & Marina

Find out more about Shelter Island

Shelter Island Chalets information

Number of reviews
4,198
Accommodation
1 Chalets
Lowest Price
$150
Highest Price
$4,291

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