Villas in Shelter Island

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Dec 19 - Dec 21
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Jan 9 - Jan 11
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Feb 6 - Feb 8

Villas in Shelter Island

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

Recommended hotels in Shelter Island

Ocean View 2 Queens | Premium bedding, pillowtop beds, blackout drapes, free WiFi
Offshore Montauk

Offshore Montauk

2.0 star property
9.2 out of 10, Wonderful, (76)
"Nice decoration, clean amenities, good stay"
United States
weihao
$166 nightly
The price is $190
Jan 1 - Jan 2, 2026
Total with taxes and fees
Offshore Montauk
Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
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 22 - Dec 23
Total with taxes and fees
Montauk Manor
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Motel in Culloden Shores

2.0 star property
8.4 out of 10, Very Good, (878)
"Really clean and nice location"
United States
Tiara
$120 nightly
The price is $138
Jan 4 - Jan 5, 2026
Total with taxes and fees
Kenny's Tipperary Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (391)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$118 nightly
The price is $135
Dec 11 - Dec 12
Total with taxes and fees
The Bentley Hotel Southampton
Property grounds
Hamlet Inn

Motel in Southampton

2.0 star property
8.6 out of 10, Excellent, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$114 nightly
The price is $128
Dec 9 - Dec 10
Total with taxes and fees
Hamlet Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Motel in Old Saybrook

2.0 star property
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
$67 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
8.0 out of 10, Very Good, (1001)
"A welcoming place with some nice touches."
United States
Leslie
$79 nightly
The price is $91
Dec 21 - Dec 22
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Property entrance
The Niantic Inn

The Niantic Inn

2.5 star property
9.2 out of 10, Wonderful, (126)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
$98 nightly
The price is $113
Dec 15 - Dec 16
Total with taxes and fees
The Niantic Inn
Exterior
Clinton Motel

Motel in Clinton

2.5 star property
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Dec 9 - Dec 10
Total with taxes and fees
Clinton Motel
Exterior
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$171 nightly
The price is $193
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Exterior
House on Chase Creek

Guesthouse in The Heights

2.5 star property
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
$104 nightly
The price is $119
Jan 6 - Jan 7, 2026
Total with taxes and fees
House on Chase Creek
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (543)
"Awesome stay!!! Great Location "
United States
Bryan
$174 nightly
The price is $199
Dec 29 - Dec 30
Total with taxes and fees
The Harbor Front Inn
Terrace/patio
Shorewood Inn

Motel in Riverhead

2.5 star property
8.4 out of 10, Very Good, (708)
"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "
United States
Shelly
$93 nightly
The price is $106
Dec 22 - Dec 23
Total with taxes and fees
Shorewood Inn
Exterior
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.8 out of 10, Good, (1002)
"Staff was kind. Easy, comfortable stay."
United States
Jake
$101 nightly
The price is $116
Dec 15 - Dec 16
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Front of property
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (226)
"Food!"
United States
Ryan
$174 nightly
The price is $199
Dec 30 - Dec 31
Total with taxes and fees
The Shoals Suites and Slips
Terrace/patio
Inn at Harbor Hill Marina

Bed & Breakfast in Niantic

3.5 star property
9.4 out of 10, Exceptional, (1004)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$159 nightly
The price is $183
Dec 9 - Dec 10
Total with taxes and fees
Inn at Harbor Hill Marina
Exterior
Liberty Inn

Liberty Inn

2.0 star property
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
$83 nightly
The price is $96
Dec 14 - Dec 15
Total with taxes and fees
Liberty Inn
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
$390 nightly
The price is $446
Dec 14 - Dec 15
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Exterior
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
$265 nightly
The price is $301
Dec 9 - Dec 10
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Exterior
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Vacation Home in 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
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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

The Sagaponack

The Sagaponack

10/10 Excellent
"Everything was amazing! Friendly service! "
Kim 3-night trip
Posted 4 days ago
The Sagaponack

Find out more about Shelter Island

Shelter Island Villas information

Number of reviews
8,600
Accommodation
36 Villas
Lowest Price
$77
Highest Price
$446

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