Villas in Shelter Island

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Villas in Shelter Island

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Recommended hotels in Shelter Island

Work and Play Special! Extended Stay Discount

Shelter Island
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
$1,165 nightly
The price is $1,331
Nov 29 - Nov 30
Total with taxes and fees
Work and Play Special! Extended Stay Discount

Offshore Montauk

2.0 star property
Montauk
9.4 out of 10, Exceptional, (70)
"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 7 - Dec 8
Total with taxes and fees
Offshore Montauk

Pier Blue Inn Old Saybrook - Essex

2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1000)
"Always a great stay at Pier Blue. Comfy bed and plenty of room."
United States
Patricia
$71 nightly
The price is $82
Dec 15 - Dec 16
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
$141 nightly
The price is $161
Dec 21 - Dec 22
Total with taxes and fees
The Harbor Front Inn

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
$156 nightly
The price is $178
Dec 8 - Dec 9
Total with taxes and fees
Montauk Manor

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
$176 nightly
The price is $201
Nov 24 - Nov 25
Total with taxes and fees
North Fork Cottages & RV Resort

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
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
$172 nightly
The price is $195
Dec 7 - Dec 8
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (438)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$99 nightly
The price is $111
Nov 24 - Nov 25
Total with taxes and fees
Hamlet Inn

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
$72 nightly
The price is $82
Nov 30 - Dec 1
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook

Kenny's Tipperary Inn

2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (877)
"Very clean and spacious room! "
United States
Mary Beth
$134 nightly
The price is $153
Nov 24 - Nov 25
Total with taxes and fees
Kenny's Tipperary Inn

Clinton Motel

2.5 star property
Clinton
8.6 out of 10, Excellent, (294)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Nov 30 - Dec 1
Total with taxes and fees
Clinton Motel

Shorewood Inn

2.5 star property
Riverhead
8.4 out of 10, Very Good, (706)
"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 7 - Dec 8
Total with taxes and fees
Shorewood Inn

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (68)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
$121 nightly
The price is $138
Nov 28 - Nov 29
Total with taxes and fees
Hampton Bays Hotel on Main

The Shoals Suites and Slips

3.5 star property
Southold
9.6 out of 10, Exceptional, (221)
"Great quick stay"
United States
Jasmine T
$177 nightly
The price is $203
Dec 13 - Dec 14
Total with taxes and fees
The Shoals Suites and Slips

The Captain Stannard

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (257)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
$160 nightly
The price is $178
Dec 15 - Dec 16
Total with taxes and fees
The Captain Stannard

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (383)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$106 nightly
The price is $122
Nov 30 - Dec 1
Total with taxes and fees
The Bentley Hotel Southampton

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1010)
"Staff was kind. Easy, comfortable stay."
United States
Jake
$101 nightly
The price is $116
Nov 30 - Dec 1
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook

Inn at Harbor Hill Marina

3.5 star property
Niantic
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$144 nightly
The price is $165
Nov 24 - Nov 25
Total with taxes and fees
Inn at Harbor Hill Marina

The Niantic Inn

2.5 star property
Niantic
9.0 out of 10, Wonderful, (121)
"Great location. Nice and clean room and property"
United States
Eric
$128 nightly
The price is $147
Nov 24 - Nov 25
Total with taxes and fees
The Niantic Inn

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (593)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$199 nightly
The price is $227
Dec 18 - Dec 19
Total with taxes and fees
Sound View Greenport
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

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