Photo by Brian V. Rowe

Search Vacation Homes in Shelter Island Heights

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Vacation Homes in Shelter Island Heights

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, (4)
"Communication was excellent. "
United States
Katy C.
The price is AED 317
AED 1,479 total
includes taxes & fees
8 Jan - 9 January 2026
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.
The price is AED 431
AED 1,333 total
includes taxes & fees
9 Jan - 10 January 2026
The Bay Cottage · Rocky Neck Park, Beach & Niantic
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 AED 14,994
AED 26,660 total
includes taxes & fees
10 Dec - 11 Dec
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is AED 346
AED 1,324 total
includes taxes & fees
18 Dec - 19 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Fridge, microwave, oven, stovetop
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.
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
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 AED 638
AED 1,529 total
includes taxes & fees
10 Dec - 11 Dec
Adorable Cottage, 5 min walk to water & town
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 AED 525
AED 1,890 total
includes taxes & fees
16 Dec - 17 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 AED 275
AED 3,235 total
includes taxes & fees
15 Dec - 16 Dec
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 AED 364
AED 4,670 total
includes taxes & fees
4 Jan - 5 January 2026
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 AED 661
AED 1,322 total
includes taxes & fees
12 Dec - 13 Dec
Stylish Modern Stay Steps from the Ocean
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 AED 16,528
AED 23,473 total
includes taxes & fees
11 Dec - 12 Dec
Sag Harbor Water View w Dock 1.5ml from town
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 AED 657
AED 1,020 total
includes taxes & fees
14 Dec - 15 Dec
American Beech in Greenport - Petite King Room 7
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 AED 14,691
AED 23,675 total
includes taxes & fees
13 Dec - 14 Dec
Spacious 5-bedroom house with water views and 2 houses from the bay.
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.
The price is AED 1,010
AED 2,019 total
includes taxes & fees
10 Dec - 11 Dec
Coastal New England Waterfront Home, Harkness Park, Casinos
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 AED 918
AED 2,128 total
includes taxes & fees
10 Dec - 11 Dec
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Microwave, oven, stovetop, dishwasher
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 AED 588
AED 754 total
includes taxes & fees
10 Dec - 11 Dec
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR
Fridge, microwave, oven, stovetop
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.
The price is AED 1,249
AED 2,493 total
includes taxes & fees
10 Dec - 11 Dec
Charming Northfork Townhouse- walk to all
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 AED 1,194
AED 2,358 total
includes taxes & fees
10 Dec - 11 Dec
Immaculate Waterfront 2 bedroom!
Fridge, microwave, oven, stovetop
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.
The price is AED 1,377
AED 2,660 total
includes taxes & fees
10 Dec - 11 Dec
Northfork Townhouse- walk to all/ newly renovated
Private kitchen
Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition

Wainscott
The price is AED 5,487
AED 7,129 total
includes taxes & fees
10 Dec - 11 Dec
Cozy 5 Bedroom With Wi-fi And Air Condition
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Heights Hotel Reviews

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

10/10 Excellent
"Extremely clean property! We were very happy and comfortable for our 5 day stay. Excellent property nicely updated and pet friendly which was a necessity since we were traveling with our pup. A+++++"
elizabeth 4-night trip
Posted 4 days ago
Best Western Niantic - New London/Mystic Area

Explore a world of travel with Expedia