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Our top choices for Shelter Island vacation homes

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, (11 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ¥17,645
¥59,747 total
includes taxes & fees
Feb 8 - Feb 9
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5 reviews)
"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 ¥15,638
¥65,240 total
includes taxes & fees
Feb 8 - Feb 9
Rogers Lake House (87) · CT College+Beach+USCGA

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ¥15,534
¥189,312 total
includes taxes & fees
Feb 9 - Feb 10
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is ¥18,449
¥56,461 total
includes taxes & fees
Mar 1 - Mar 2
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ¥23,826
¥81,980 total
includes taxes & fees
Feb 11 - Feb 12
Beachside Bliss w/ Game Room, Gym & Golf Green

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"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 ¥28,049
¥56,254 total
includes taxes & fees
Feb 6 - Feb 7
Stylish Modern Stay Steps from the Ocean

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"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 ¥15,427
¥152,400 total
includes taxes & fees
Feb 8 - Feb 9
Blackberry: Private home with jacuzzi year-round

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, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ¥15,427
¥208,302 total
includes taxes & fees
Feb 18 - Feb 19
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is ¥17,920
¥77,837 total
includes taxes & fees
Feb 22 - Feb 23
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ¥16,985
¥29,201 total
includes taxes & fees
Feb 8 - Feb 9
American Beech in Greenport - Petite King Room 7

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 ¥210,371
¥355,893 total
includes taxes & fees
Feb 14 - Feb 15
Sag Harbor Water View w Dock 1.5ml from town

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"We loved our stay!"
United States
Deana L.
The price is ¥34,922
¥85,196 total
includes taxes & fees
Feb 6 - Feb 7
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is ¥467,490
¥914,929 total
includes taxes & fees
Mar 7 - Mar 8
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (8 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is ¥38,958
¥78,539 total
includes taxes & fees
Feb 15 - Feb 16
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is ¥232,810
¥301,059 total
includes taxes & fees
Feb 6 - Feb 7
Cozy 5 Bedroom With Wi-fi And Air Condition

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 ¥623,320
¥1,004,835 total
includes taxes & fees
Mar 8 - Mar 9
Spacious 5-bedroom house with water views and 2 houses from the bay.

Beach cottage, private road, private beach, private mooring, private parking.

Beach cottage, private road, private beach, private mooring, private parking.
Laurel
10.0 out of 10, Exceptional, (1 review)
The price is ¥42,366
¥127,104 total
includes taxes & fees
Feb 16 - Feb 17
Beach cottage, private road, private beach, private mooring, private parking.

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is ¥42,074
¥90,264 total
includes taxes & fees
Feb 9 - Feb 10
Northfork Townhouse walk to all

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"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 ¥50,645
¥100,772 total
includes taxes & fees
Feb 8 - Feb 9
Immaculate Waterfront 2 bedroom!

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is ¥38,568
¥85,903 total
includes taxes & fees
Feb 9 - Feb 10
Renovated Townhouse walk to all
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

Find out more about Shelter Island

Shelter Island Vacation Homes information

Number of reviews
181
Accommodation
1792 Vacation Homes
Lowest Price
¥29,201
Highest Price
¥1,004,835