Photo by Brian V. Rowe

Search Vacation Homes in Shelter Island Heights

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Shelter Island Heights vacation homes

Smart TV, fireplace, books
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Vacation Home in Waterford

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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
Jan 5 - Jan 6, 2026
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

Vacation Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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.
$6,469 nightly
The price is $7,391
Jan 5 - Jan 6, 2026
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
$356 nightly
The price is $403
Jan 5 - Jan 6, 2026
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
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
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Smart TV, fireplace
Spacious 5-bedroom house with water views and 2 houses from the bay.

Vacation Home in Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.
$5,636 nightly
The price is $6,439
Dec 27 - Dec 28
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Outdoor dining
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
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
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$458 nightly
The price is $518
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
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.
$799 nightly
The price is $913
Jan 4 - Jan 5, 2026
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,085 nightly
The price is $1,240
Dec 23 - Dec 24
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Terrace/patio
American Beech in Greenport - Petite King Room 7

Vacation Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$243 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Property grounds
Stylish Modern Stay Steps from the Ocean

Vacation Home in Clinton

Stylish Modern Stay Steps from the Ocean
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 23 - Dec 24
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Interior
Sag Harbor Water View w Dock 1.5ml from town

Vacation Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town
$5,594 nightly
The price is $6,391
Dec 25 - Dec 26
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Interior
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Vacation Home in Saybrook Manor

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
$511 nightly
The price is $579
Jan 12 - Jan 13, 2026
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Outdoor dining
Coastal New England Waterfront Home, Harkness Park, Casinos

Vacation Home in Waterford

Coastal New England Waterfront Home, Harkness Park, Casinos
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 26 - Dec 27
Total with taxes and fees
Coastal New England Waterfront Home, Harkness Park, Casinos
Dining
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Vacation Home in East Hampton North

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
$785 nightly
The price is $837
Dec 29 - Dec 30
Total with taxes and fees
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
Smart TV, fireplace
Northfork Townhouse- walk to all/ newly renovated

Vacation Home in Greenport

Northfork Townhouse- walk to all/ newly renovated
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.
$549 nightly
The price is $627
Dec 23 - Dec 24
Total with taxes and fees
Northfork Townhouse- walk to all/ newly renovated
Property grounds
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Vacation Home in Southampton

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
10.0 out of 10, Exceptional, (15)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
$1,504 nightly
The price is $1,593
Jan 5 - Jan 6, 2026
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Interior
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Vacation Home in East Hampton

Upscale Hamptons Home: 1 Mi to Sammys Beach!
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!
Dining
Charming Northfork Townhouse- walk to all

Vacation Home in Greenport

Charming Northfork Townhouse- walk to all
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.
$600 nightly
The price is $686
Dec 23 - Dec 24
Total with taxes and fees
Charming Northfork Townhouse- walk to all
Dining
Immaculate Waterfront 2 bedroom!

Vacation Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
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.
$566 nightly
The price is $647
Dec 23 - Dec 24
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything was wonderful. Staff was friendly, very clean,we enjoyed it."
Donna 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

Find out more about Shelter Island Heights

Shelter Island Heights Vacation Homes information

Number of reviews
288
Accommodation
1814 Vacation Homes
Lowest Price
$278
Highest Price
$7,391

Explore a world of travel with Expedia