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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Vacation Homes in Shelter Island

Property grounds
Work and Play Special! Extended Stay Discount

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.
The price is SAR 2,700
SAR 4,992 total
includes taxes & fees
22 Nov - 23 Nov
Work and Play Special! Extended Stay Discount
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA

Old Lyme
10.0 out of 10, Exceptional, (3)
"We were very comfortable during our stay. The amenities at the house and in the vicinity were great. Our hosts were very responsive in answering our questions. We watched the World Series on the large screen TV in the den. All the family members we had stay with us during the week had ample space to sleep and stretch out. We loved the Yoga studio too. Many thanks!"
United States
Nicole B.
The price is SAR 324
SAR 1,510 total
includes taxes & fees
3 Dec - 4 Dec
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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 1,358 total
includes taxes & fees
30 Nov - 1 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays
10.0 out of 10, Exceptional, (12)
"This is a simple house with a great view right on the water. The beds and bedding were comfortable. Despite being on the water, it has a nice yard and little beach area. "
United States
Coleman H.
The price is SAR 371
SAR 4,525 total
includes taxes & fees
24 Nov - 25 Nov
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
The price is SAR 365
SAR 944 total
includes taxes & fees
30 Nov - 1 Dec
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is SAR 536
SAR 1,930 total
includes taxes & fees
9 Dec - 10 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round

East Hampton
9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is SAR 206
SAR 3,209 total
includes taxes & fees
24 Nov - 25 Nov
Blackberry: Private home with jacuzzi year-round
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Hampon Bays
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is SAR 371
SAR 4,769 total
includes taxes & fees
3 Dec - 4 Dec
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Private kitchen
Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean

Clinton
10.0 out of 10, Exceptional, (1)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is SAR 540
SAR 1,146 total
includes taxes & fees
22 Nov - 23 Nov
Stylish Modern Stay Steps from the Ocean
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is SAR 15,189
SAR 27,127 total
includes taxes & fees
22 Nov - 23 Nov
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town

Westbrook Center
9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is SAR 652
SAR 1,562 total
includes taxes & fees
23 Nov - 24 Nov
Adorable Cottage, 5 min walk to water & town
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.

Sag Harbor
The price is SAR 15,001
SAR 24,123 total
includes taxes & fees
25 Nov - 26 Nov
Spacious 5-bedroom house with water views and 2 houses from the bay.
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Saybrook Manor
9.6 out of 10, Exceptional, (133)
"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "
United States
Rob C.
The price is SAR 750
SAR 1,931 total
includes taxes & fees
22 Dec - 23 Dec
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Interior
Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos

Waterford
10.0 out of 10, Exceptional, (126)
"Repeat renter! Great location, super clean house, A host: very responsive; will be back again! "
United States
Carrie B.
The price is SAR 1,234
SAR 2,325 total
includes taxes & fees
23 Nov - 24 Nov
Coastal New England Waterfront Home, Harkness Park, Casinos
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is SAR 671
SAR 1,045 total
includes taxes & fees
4 Dec - 5 Dec
American Beech in Greenport - Petite King Room 7
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town

Bay Point
The price is SAR 16,876
SAR 23,977 total
includes taxes & fees
23 Nov - 24 Nov
Sag Harbor Water View w Dock 1.5ml from town
Interior
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR

House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR

2.0 star property
Clinton
The price is SAR 601
SAR 770 total
includes taxes & fees
23 Nov - 24 Nov
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR
Terrace/patio
Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!

Hampton Bays
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is SAR 1,219
SAR 2,352 total
includes taxes & fees
23 Nov - 24 Nov
Immaculate Waterfront 2 bedroom!
Terrace/patio
Beautifully farmhouse

Beautifully farmhouse

Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
The price is SAR 2,250
SAR 4,405 total
includes taxes & fees
4 Dec - 5 Dec
Beautifully farmhouse
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom

Southampton
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is SAR 1,688
SAR 4,161 total
includes taxes & fees
23 Nov - 24 Nov
Minutes from the beach, brand new 4 bedroom
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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Staff was kind. Easy, comfortable stay."
Jake 3-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook

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