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Check prices for these dates

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Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Shelter Island Chalets

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Recommended hotels in Shelter Island

Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1006)
"Perfect spot for my visit"
The price is CA $139
CA $160 total
includes taxes & fees
Sep 15 - Sep 16
Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1008)
"Good budget friendly hotel"
The price is CA $111
CA $127 total
includes taxes & fees
Sep 1 - Sep 2
Pier Blue Inn Old Saybrook - Essex
Clinton Motel
Property grounds

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (269)
"Great stay. Fantastic location. Wonderful motel providing everything you need. Clean, comfortable and excellent value."
The price is CA $109
CA $126 total
includes taxes & fees
Sep 1 - Sep 2
Clinton Motel
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is CA $1,106
CA $1,986 total
includes taxes & fees
Sep 14 - Sep 15
Work and Play Special! Extended Stay Discount
Liberty Inn
Property grounds

Liberty Inn

2.0 star property
7.4 out of 10, Good, (620)
"Service at front desk was very good!"
The price is CA $108
CA $125 total
includes taxes & fees
Sep 25 - Sep 26
Liberty Inn
Shorewood Inn
Terrace/patio

Shorewood Inn

2.5 star property
8.6 out of 10, Excellent, (676)
"Good place to stay"
The price is CA $172
CA $196 total
includes taxes & fees
Aug 26 - Aug 27
Shorewood Inn
Super 8 by Wyndham Old Saybrook
Property amenity

Super 8 by Wyndham Old Saybrook

2.0 star property
7.0 out of 10, Good, (895)
"This was convenient to the highway and to a wedding we were attending at Water's Edge."
The price is CA $103
CA $122 total
includes taxes & fees
Aug 26 - Aug 27
Super 8 by Wyndham Old Saybrook
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, (444)
"Definitely an older property, but staff were helpful people and our room was clean and quiet. Easy car ride to get to the ocean."
The price is CA $105
CA $121 total
includes taxes & fees
Sep 9 - Sep 10
Econo Lodge Inn & Suites Old Saybrook Westbrook
Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.4 out of 10, Exceptional, (186)
"Close to town and pool was great!"
The price is CA $175
CA $200 total
includes taxes & fees
Sep 2 - Sep 3
Greenporter Hotel
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (74)
"Awesome all around! Staff was super nice "
The price is CA $409
CA $514 total
includes taxes & fees
Sep 21 - Sep 22
The Pridwin Hotel
The Bentley Hotel Southampton
Terrace/patio

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (322)
"Great place!"
The price is CA $290
CA $371 total
includes taxes & fees
Sep 3 - Sep 4
The Bentley Hotel Southampton
Lamplighter Motel - Clinton, Connecticut
Exterior

Lamplighter Motel - Clinton, Connecticut

2.5 star property
6.2 out of 10, (214)
"Would stay again. "
The price is CA $95
CA $110 total
includes taxes & fees
Sep 7 - Sep 8
Lamplighter Motel - Clinton, Connecticut
Hampton's Vacation Inn
Apartment, 2 Bedrooms | Private kitchen

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (303)
"Our stay at Hampton’s Vacation Inn was excellent. The cottage was awesome, the staff was amazing, and the room was clean and very accessible to everything. I would definitely stay here again and highly recommend it to others."
The price is CA $249
CA $284 total
includes taxes & fees
Aug 27 - Aug 28
Hampton's Vacation Inn
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (75)
"The House on Chase Creek is beautiful. It's an old house but everything is updated, clean and comfortable. "
The price is CA $340
CA $388 total
includes taxes & fees
Sep 8 - Sep 9
House on Chase Creek
The Niantic Inn
Beach nearby

The Niantic Inn

2.0 star property
9.2 out of 10, Wonderful, (104)
"Enjoyed my stay"
The price is CA $228
CA $263 total
includes taxes & fees
Sep 9 - Sep 10
The Niantic Inn
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (504)
"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."
The price is CA $386
CA $444 total
includes taxes & fees
Aug 28 - Aug 29
Copper Beech Inn
Ocean Vista Resort
View from property

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (187)
"It waa great for traveling with kids. Close to the beach and my kids loved the indoor pool!"
The price is CA $234
CA $267 total
includes taxes & fees
Sep 21 - Sep 22
Ocean Vista Resort
Hampton Bays Hotel on Main
Deluxe Double Room, 1 King Bed, City View

Hampton Bays Hotel on Main

2.0 star property
6.8 out of 10, (53)
"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!"
The price is CA $140
CA $161 total
includes taxes & fees
Sep 2 - Sep 3
Hampton Bays Hotel on Main
Ruschmeyers Hotel
Exterior

Ruschmeyers Hotel

3.0 star property
8.0 out of 10, Very good, (66)
"Great place! Be back in Aug"
The price is CA $247
CA $310 total
includes taxes & fees
Sep 21 - Sep 22
Ruschmeyers Hotel
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (242)
"Everything was fantastic, will stay again!"
The price is CA $296
CA $329 total
includes taxes & fees
Sep 21 - Sep 22
The Captain Stannard
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

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"We have stayed at a lot of different places over the years, But this by far was our best trip to date. The property was all that was promised. Clean and beautiful. It’s a must stay if your heading to Montauk."
William 2-night trip
Posted 8 hours ago
Montauk Blue Hotel