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Check prices for these dates

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

Houseboats in Shelter Island

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

Recommended hotels in Shelter Island

Exterior
Offshore Montauk

Offshore Montauk

2.0 star property
9.2 out of 10, Wonderful, (76)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is SAR 436
SAR 712 total
includes taxes & fees
1 Jan - 2 January 2026
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
The price is SAR 520
SAR 668 total
includes taxes & fees
9 Dec - 10 Dec
Montauk Manor
Front of property
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
Kenny's Tipperary Inn
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
The price is SAR 351
SAR 404 total
includes taxes & fees
21 Dec - 22 Dec
The Niantic 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
The price is SAR 441
SAR 508 total
includes taxes & fees
11 Dec - 12 Dec
The Bentley Hotel Southampton
Exterior
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
The price is SAR 372
SAR 480 total
includes taxes & fees
9 Dec - 10 Dec
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
The price is SAR 252
SAR 289 total
includes taxes & fees
4 Jan - 5 January 2026
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
Pier Blue Inn Old Saybrook - Essex
Free self parking
Clinton Motel

Motel in Clinton

2.5 star property
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is SAR 293
SAR 337 total
includes taxes & fees
9 Dec - 10 Dec
Clinton Motel
Exterior detail
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
The price is SAR 290
SAR 731 total
includes taxes & fees
2 Jan - 3 January 2026
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
The price is SAR 391
SAR 447 total
includes taxes & fees
6 Jan - 7 January 2026
House on Chase Creek
Property entrance
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (542)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is SAR 492
SAR 746 total
includes taxes & fees
29 Dec - 30 Dec
The Harbor Front Inn
Terrace/patio
Shorewood Inn

Motel in Riverhead

2.5 star property
8.4 out of 10, Very Good, (707)
"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "
United States
Shelly
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
The price is SAR 380
SAR 437 total
includes taxes & fees
14 Dec - 15 Dec
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
The price is SAR 634
SAR 724 total
includes taxes & fees
14 Dec - 15 Dec
The Shoals Suites and Slips
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
The price is SAR 206
SAR 1,672 total
includes taxes & fees
14 Dec - 15 Dec
Seabreeze #3: Cozy Cottage by the beach
Front of property - evening/night
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
The price is SAR 597
SAR 686 total
includes taxes & fees
9 Dec - 10 Dec
Inn at Harbor Hill Marina
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.
The price is SAR 535
SAR 1,167 total
includes taxes & fees
9 Dec - 10 Dec
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.
The price is SAR 358
SAR 1,359 total
includes taxes & fees
18 Dec - 19 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Outdoor pool, sun loungers
Daunt's Albatross Motel

Motel in Downtown Montauk

2.0 star property
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
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

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