Search Residences in Shelter Island

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb
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

Offshore Montauk
2.0 star property
9.2 out of 10, Wonderful, (77)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is AED 426
AED 697 total
includes taxes & fees
4 Jan - 5 January 2026
Offshore Montauk
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Motel in Southampton

Hamlet Inn
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
The price is AED 327
AED 423 total
includes taxes & fees
11 Dec - 12 Dec
Hamlet Inn
Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

Montauk Manor
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
The price is AED 509
AED 653 total
includes taxes & fees
11 Dec - 12 Dec
Montauk Manor
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Motel in Culloden Shores

Kenny's Tipperary Inn
2.0 star property
8.4 out of 10, Very Good, (878)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
9.6 out of 10, Exceptional, (392)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is AED 420
AED 483 total
includes taxes & fees
14 Dec - 15 Dec
The Bentley Hotel Southampton
Standard Studio, 1 King Bed, Non Smoking | Premium bedding, free WiFi, bed sheets
The Niantic Inn

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
The price is AED 292
AED 335 total
includes taxes & fees
15 Dec - 16 Dec
The Niantic Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Motel in Old Saybrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
The price is AED 246
AED 283 total
includes taxes & fees
16 Dec - 17 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
8.0 out of 10, Very Good, (1000)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
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
The price is AED 279
AED 710 total
includes taxes & fees
5 Jan - 6 January 2026
The Stern at Soundview · Beach+Ocean+Sunrise
View from property
House on Chase Creek

Guesthouse in The Heights

House on Chase Creek
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
The price is AED 382
AED 437 total
includes taxes & fees
6 Jan - 7 January 2026
House on Chase Creek
Property grounds
Clinton Motel

Motel in Clinton

Clinton Motel
2.5 star property
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is AED 286
AED 329 total
includes taxes & fees
15 Dec - 16 Dec
Clinton Motel
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (544)
"Awesome stay!!! Great Location "
United States
Bryan
The price is AED 482
AED 730 total
includes taxes & fees
24 Dec - 25 Dec
The Harbor Front Inn
Property grounds
Inn at Harbor Hill Marina

Bed & Breakfast in Niantic

Inn at Harbor Hill Marina
3.5 star property
9.4 out of 10, Exceptional, (1000)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is AED 584
AED 672 total
includes taxes & fees
14 Dec - 15 Dec
Inn at Harbor Hill Marina
Terrace/patio
Shorewood Inn

Motel in Riverhead

Shorewood Inn
2.5 star property
8.4 out of 10, Very Good, (708)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
7.8 out of 10, Good, (1003)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is AED 371
AED 427 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Old Saybrook - Westbrook
Garden Suite King | Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
9.6 out of 10, Exceptional, (227)
"Food!"
United States
Ryan
The price is AED 627
AED 716 total
includes taxes & fees
25 Dec - 26 Dec
The Shoals Suites and Slips
Property grounds
Liberty Inn

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
The price is AED 294
AED 338 total
includes taxes & fees
15 Dec - 16 Dec
Liberty Inn
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1)
The price is AED 202
AED 1,678 total
includes taxes & fees
4 Jan - 5 January 2026
Seabreeze #3: Cozy Cottage by the beach
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
7.2 out of 10, Good, (974)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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.
The price is AED 496
AED 1,106 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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 Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Yes"
Ray 1-night trip
Posted 2 days ago
The Harbor Front Inn