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Search Vacation Homes in Shelter Island Heights

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Shelter Island Heights vacation homes

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

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.
$356 nightly
The price is $403
Dec 14 - Dec 15
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV, fireplace, books
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

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11)
"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 18 - Dec 19
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Smart TV, fireplace, table tennis, books
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

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 15 - Dec 16
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Beach nearby
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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 15 - Dec 16
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Dining
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
2.0 star property
Clinton
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
$451 nightly
The price is $510
Dec 14 - Dec 15
Total with taxes and fees
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

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.
$453 nightly
The price is $513
Dec 16 - Dec 17
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

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 15 - Dec 16
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Outdoor dining
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

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
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Property grounds
Stylish Modern Stay Steps from the Ocean

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.
$298 nightly
The price is $337
Dec 15 - Dec 16
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Interior
Adorable Cottage, 5 min walk to water & town

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 14 - Dec 15
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Smart TV, fireplace
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.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
$5,625 nightly
The price is $6,427
Dec 15 - Dec 16
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$242 nightly
The price is $277
Dec 14 - Dec 15
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Outdoor dining
Coastal New England Waterfront Home, Harkness Park, Casinos

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.
$486 nightly
The price is $550
Dec 14 - Dec 15
Total with taxes and fees
Coastal New England Waterfront Home, Harkness Park, Casinos
Interior
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

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.
$510 nightly
The price is $578
Dec 14 - Dec 15
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Interior
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR

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
$182 nightly
The price is $206
Dec 14 - Dec 15
Total with taxes and fees
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR
Dining
Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all
Greenport
10.0 out of 10, Exceptional, (5)
"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.
$589 nightly
The price is $673
Dec 13 - Dec 14
Total with taxes and fees
Charming Northfork Townhouse- walk to all
Interior
Sag Harbor Water View w Dock 1.5ml from town

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 13 - Dec 14
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Dining
Immaculate Waterfront 2 bedroom!

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.
$547 nightly
The price is $625
Dec 14 - Dec 15
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Interior
Upscale Hamptons Home: 1 Mi to Sammys Beach!

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!
Smart TV, fireplace
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated
Greenport
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
$640 nightly
The price is $731
Dec 14 - Dec 15
Total with taxes and fees
Northfork Townhouse- walk to all/ newly renovated
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 Heights Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay."
Rachel 1-night trip
Posted 3 days ago
Gurney's Montauk Resort & Seawater Spa

Find out more about Shelter Island Heights

Shelter Island Heights Vacation Homes information

Number of reviews
287
Accommodation
1814 Vacation Homes
Lowest Price
$277
Highest Price
$7,259

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