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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
5 bedrooms, in-room safe, desk, free WiFi

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (52)
"Beautiful pool, badminton net, lots of outdoor seating areas. Location is easy, very close to ferry and nature preserve."
$1,257 nightly
The price is $1,436
Nov 5 - Nov 6
Total with taxes and fees
Work and Play Special! Extended Stay Discount
Clinton Motel
Exterior

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (280)
"Great staff and clean rooms"
$78 nightly
The price is $90
Oct 13 - Oct 14
Total with taxes and fees
Clinton Motel
Pier Blue Inn Old Saybrook - Essex
Exterior

Pier Blue Inn Old Saybrook - Essex

2.0 star property
8.0 out of 10, Very Good, (1005)
"Very friendly and helpful staff."
$80 nightly
The price is $93
Oct 22 - Oct 23
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook
Exterior

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1006)
"We have stayed there before so have been pleased with it."
$94 nightly
The price is $108
Nov 2 - Nov 3
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Liberty Inn
Exterior

Liberty Inn

2.0 star property
7.4 out of 10, Good, (631)
"Well located for getting to the places we wanted to be. This is an older property, but well taken care of and service was very good. I wouldn’t hesitate to stay here again. "
$83 nightly
The price is $96
Nov 2 - Nov 3
Total with taxes and fees
Liberty Inn
Greenporter Hotel
Garden

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (262)
"Staff was amazing and this hotel is in the perfect location "
$156 nightly
The price is $179
Oct 13 - Oct 14
Total with taxes and fees
Greenporter Hotel
Ocean Vista Resort
Balcony

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (196)
"Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!"
$134 nightly
The price is $153
Oct 26 - Oct 27
Total with taxes and fees
Ocean Vista Resort
Inn at Harbor Hill Marina
Terrace/patio

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1003)
"Clean, cute property with super friendly staff. Breakfast was an added bonus."
$169 nightly
The price is $194
Nov 2 - Nov 3
Total with taxes and fees
Inn at Harbor Hill Marina
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (456)
"the so-called breakfast was absolute minimum only thing available was make your own waffle"
$72 nightly
The price is $82
Nov 2 - Nov 3
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Silver Sands Motel & Beach Bungalows
Beach bar

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (134)
"Beautiful beach all was great, loved breakfast At on site diner Nookies!"
$256 nightly
The price is $293
Oct 22 - Oct 23
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
Hamlet Inn
Property grounds

Hamlet Inn

2.0 star property
8.6 out of 10, Excellent, (427)
"Great Staff"
$160 nightly
The price is $180
Oct 9 - Oct 10
Total with taxes and fees
Hamlet Inn
Hampton's Vacation Inn
Exterior

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (317)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
$126 nightly
The price is $144
Oct 22 - Oct 23
Total with taxes and fees
Hampton's Vacation Inn
Aqualina Inn Montauk
Seasonal outdoor pool, sun loungers

Aqualina Inn Montauk

2.5 star property
9.6 out of 10, Exceptional, (483)
"Walk to the beach and go area restaurants was great. Staff was very nice."
$123 nightly
The price is $141
Oct 9 - Oct 10
Total with taxes and fees
Aqualina Inn Montauk
New and Modern Bridgehampton Accommodations
Outdoor pool, a heated pool

New and Modern Bridgehampton Accommodations

2.0 star property
9.6 out of 10, Exceptional, (14)
"Had a great stay here with a small group. Host was very accommodating and responsive. "
$384 nightly
The price is $438
Oct 9 - Oct 10
Total with taxes and fees
New and Modern Bridgehampton Accommodations
Lamplighter Motel - Clinton, Connecticut
Exterior

Lamplighter Motel - Clinton, Connecticut

2.5 star property
6.4 out of 10, (218)
"Would stay again. "
$69 nightly
The price is $79
Oct 9 - Oct 10
Total with taxes and fees
Lamplighter Motel - Clinton, Connecticut
Hero Beach Club
Hero King Patio Deluxe | Terrace/patio

Hero Beach Club

4.0 star property
9.0 out of 10, Wonderful, (195)
"Beach view and cozy vibes"
$212 nightly
The price is $243
Oct 26 - Oct 27
Total with taxes and fees
Hero Beach Club
House on Chase Creek
Exterior

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (77)
" 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 ! "
$185 nightly
The price is $211
Nov 3 - Nov 4
Total with taxes and fees
House on Chase Creek
Hampton Bays Hotel on Main
Exterior

Hampton Bays Hotel on Main

2.0 star property
7.0 out of 10, Good, (63)
"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!"
$121 nightly
The price is $138
Nov 2 - Nov 3
Total with taxes and fees
Hampton Bays Hotel on Main
The Bentley Hotel Southampton
Terrace/patio

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (350)
"Return visitor. Great stay."
$160 nightly
The price is $183
Nov 2 - Nov 3
Total with taxes and fees
The Bentley Hotel Southampton
The Niantic Inn
Property entrance

The Niantic Inn

2.0 star property
9.0 out of 10, Wonderful, (111)
"Nice place and town "
$147 nightly
The price is $170
Oct 30 - Oct 31
Total with taxes and fees
The Niantic Inn
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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Exceptional in every way"
Barbara 3-night trip
Posted 2 days ago
Beachcomber Resort at Montauk

Find out more about Shelter Island

Find out more about Shelter Island

Shelter Island Villas information

Number of reviews
6,712
Accommodation
39 Villas
Lowest Price
$79
Highest Price
$1,436

Frequently asked questions

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