Search Vacation Homes in Shelter Island

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Dec 12 - Dec 14
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Vacation Homes in Shelter Island

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.
$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
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

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
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

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
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.
$432 nightly
The price is $489
Dec 9 - Dec 10
Total with taxes and fees
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.
$771 nightly
The price is $881
Dec 4 - Dec 5
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
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.
$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
Outdoor spa tub
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.
$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
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.
$291 nightly
The price is $330
Dec 5 - Dec 6
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
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.
$368 nightly
The price is $416
Dec 4 - Dec 5
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
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.
$455 nightly
The price is $515
Dec 4 - Dec 5
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
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
$243 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
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
$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
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)
"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
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
$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.
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
$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
Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

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!
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.
$562 nightly
The price is $642
Dec 4 - Dec 5
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Fridge, oven, stovetop, dishwasher
Upscale Hamptons Home: 1 Mi to Sammys Beach!

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!
Terrace/patio
Beautifully farmhouse

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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Lovely rooms and loved the fireplace. Great stay. Awesome few days away from real life!"
Andrew 2-night trip
Posted 3 days ago
Saybrook Point Resort & Marina

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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