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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Shelter Island Heights holiday homes

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, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is £883
includes taxes & fees
12 Feb - 13 Feb
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Pool

Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids

Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
The price is £455
includes taxes & fees
13 Feb - 14 Feb
Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids
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
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is £340
includes taxes & fees
3 Mar - 4 Mar
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Dining

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
East Hampton North
The price is £472
includes taxes & fees
13 Feb - 14 Feb
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
TV, fireplace, stereo, offices

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is £445
includes taxes & fees
13 Feb - 14 Feb
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is £363
includes taxes & fees
24 Feb - 25 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is £371
includes taxes & fees
17 Feb - 18 Feb
Beachside Bliss w/ Game Room, Gym & Golf Green
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, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £936
includes taxes & fees
18 Feb - 19 Feb
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
Clinton
10.0 out of 10, Exceptional, (1 review)
"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 £247
includes taxes & fees
22 Feb - 23 Feb
Stylish Modern Stay Steps from the Ocean
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 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is £148
includes taxes & fees
17 Feb - 18 Feb
American Beech in Greenport - Petite King Room 7
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 reviews)
"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 £711
includes taxes & fees
24 Feb - 25 Feb
Blackberry: Private home with jacuzzi year-round
Smart TV, fireplace, ping pong, 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
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is £4,274
includes taxes & fees
2 Mar - 3 Mar
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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5 reviews)
"We were very comfortable during our stay. The amenities at the house and in the vicinity were great. Our hosts were very responsive in answering our questions. We watched the World Series on the large screen TV in the den. All the family members we had stay with us during the week had ample space to sleep and stretch out. We loved the Yoga studio too. Many thanks!"
United States
Nicole B.
The price is £507
includes taxes & fees
13 Feb - 14 Feb
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is £368
includes taxes & fees
15 Feb - 16 Feb
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"We loved our stay!"
United States
Deana L.
The price is £392
includes taxes & fees
12 Feb - 13 Feb
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
On the beach, sun-loungers, beach towels

Beach cottage, private road, private beach, private mooring, private parking.

Beach cottage, private road, private beach, private mooring, private parking.
Laurel
10.0 out of 10, Exceptional, (1 review)
The price is £574
includes taxes & fees
16 Feb - 17 Feb
Beach cottage, private road, private beach, private mooring, private parking.
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.
Sag Harbor
The price is £4,802
includes taxes & fees
16 Feb - 17 Feb
Spacious 5-bedroom house with water views and 2 houses from the bay.
Outdoor dining

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (126 reviews)
"Great property!"
United States
Matthew B.
The price is £391
includes taxes & fees
15 Feb - 16 Feb
Coastal New England Waterfront Home, Harkness Park, Casinos
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"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 £408
includes taxes & fees
12 Feb - 13 Feb
Northfork Townhouse walk to all
Dining

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"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 £469
includes taxes & fees
15 Feb - 16 Feb
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.
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Top Shelter Island Heights Hotel Reviews

Montauk Manor

Montauk Manor

10/10 Excellent
"Beautiful room and beautiful setting. Love the fireplace!"
Daniel 1-night trip
Posted 1 day ago
Montauk Manor

Find out more about Shelter Island Heights

Shelter Island Heights Holiday Homes information

Number of reviews
288
Accommodation
1813 Holiday Homes
Lowest Price
£148
Highest Price
£4,802