Search Vacation Homes in Shelter Island

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Vacation Homes in Shelter Island

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.
$319 nightly
The price is $361
Dec 4 - Dec 5
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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

Old Lyme
10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
$354 nightly
The price is $401
Dec 4 - Dec 5
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
East Lyme
9.0 out of 10, Wonderful, (4)
"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.
$323 nightly
The price is $365
Dec 7 - Dec 8
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays
9.6 out of 10, Exceptional, (13)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,085 nightly
The price is $1,240
Dec 7 - Dec 8
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

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.
$432 nightly
The price is $489
Dec 9 - Dec 10
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green

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.
$771 nightly
The price is $881
Dec 4 - Dec 5
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round

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.
$6,353 nightly
The price is $7,259
Dec 8 - Dec 9
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

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.
$1,113 nightly
The price is $1,272
Dec 10 - Dec 11
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

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.
$291 nightly
The price is $330
Dec 5 - Dec 6
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean

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.
$368 nightly
The price is $416
Dec 4 - Dec 5
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town

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.
$455 nightly
The price is $515
Dec 4 - Dec 5
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
$243 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7

Sag Harbor Water View w Dock 1.5ml from town

Bay Point
$5,596 nightly
The price is $6,393
Dec 6 - Dec 7
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town

Coastal New England Waterfront Home, Harkness Park, Casinos

Waterford
10.0 out of 10, Exceptional, (126)
"Wonderful location (very close to downtown Niantic); clean, bright, beautiful home; well appointed kitchen overall; loved gate at top of stairs, rail for bottom bunk and high chair since I have a toddler; owner was very responsive, kind and helpful when needed. I would definitely recommend and stay again!"
United States
Anne M.
$548 nightly
The price is $620
Dec 4 - Dec 5
Total with taxes and fees
Coastal New England Waterfront Home, Harkness Park, Casinos

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

Sag Harbor
$5,630 nightly
The price is $6,432
Dec 8 - Dec 9
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.

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

2.0 star property
Clinton
$181 nightly
The price is $205
Dec 4 - Dec 5
Total with taxes and fees
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton
9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
$711 nightly
The price is $812
Dec 4 - Dec 5
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

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.
$562 nightly
The price is $642
Dec 4 - Dec 5
Total with taxes and fees
Immaculate Waterfront 2 bedroom!

Upscale Hamptons Home: 1 Mi to Sammys Beach!

East Hampton
9.4 out of 10, Exceptional, (3)
"Wonderful property. Lisette was a fantastic host and her home updated and modern. "
United States
Joanna D.
$1,085 nightly
The price is $1,240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Beautifully farmhouse

Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,027 nightly
The price is $1,173
Dec 4 - Dec 5
Total with taxes and fees
Beautifully farmhouse
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
293
Accommodation
1793 Vacation Homes
Lowest Price
$278
Highest Price
$7,259

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