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Holiday Homes in Shelter Island Heights

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Our top choices for Shelter Island Heights holiday homes

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (7 reviews)
"We had a very nice stay at Roger’s Lake! The house was so cool! It had all the amenities we needed and the location was charming and peaceful. In particular, the beds are really comfortable! They have this awesome exercise room where you can stretch out and enjoy the light. The host, Peter, was especially easy to work with and was very communicative. My family and I are hoping to come back soon for another stay."
United States
Andrea
The price is €381
includes taxes & fees
14 Jun - 15 Jun
Rogers Lake House (87) · CT College+Beach+USCGA

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, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is €394
includes taxes & fees
16 Jun - 17 Jun
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 reviews)
"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 €368
includes taxes & fees
16 Jun - 17 Jun
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is €377
includes taxes & fees
16 Jun - 17 Jun
Adorable Cottage, 5 min walk to water & town

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (59 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is €290
includes taxes & fees
15 Jun - 16 Jun
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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, (12 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €521
includes taxes & fees
7 Jul - 8 Jul
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Lake House - A

Lake House - A
East Lyme
The price is €475
includes taxes & fees
15 Jun - 16 Jun
Lake House - A

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
10.0 out of 10, Exceptional, (20 reviews)
"Great host & location. Would stay again"
United States
Chris H.
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay at this cottage. It was comfortable, beautifully decorated, and exceptionally clean. Even though the weather during our trip was terrible, we still thoroughly enjoyed our time there.The hosts were very helpful and provided all the information we needed about the cottage as well as local attractions and activities. Overall, it was an excellent experience, and I would absolutely give it 5 stars."
United States
Erin M.
The price is €537
includes taxes & fees
14 Jun - 15 Jun
NEW Coastal Cottage 2 Miles to Beach + Lake Access

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, (138 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is €668
includes taxes & fees
15 Jun - 16 Jun
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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 €512
includes taxes & fees
15 Jun - 16 Jun
Beachside Bliss w/ Game Room, Gym & Golf Green

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
East Lyme
9.8 out of 10, Exceptional, (23 reviews)
"I’ve stayed at this property for 3 summers in a row and every time it has been perfect. Lots of room, very clean and a perfect view!"
United States
Elisa N.
The price is €2,136
includes taxes & fees
20 Jun - 21 Jun
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (132 reviews)
"Great property!"
United States
Matthew B.
The price is €681
includes taxes & fees
18 Jun - 19 Jun
Coastal New England Waterfront Home, Harkness Park, Casinos

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is €1,034
includes taxes & fees
16 Jun - 17 Jun
Black Swan Beachfront Home with Jacuzzi year round

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
The price is €547
includes taxes & fees
29 Jun - 30 Jun
Hampton Bays Townhouse - Pool, Beach Access

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €297
includes taxes & fees
24 Jun - 25 Jun
American Beech in Greenport - Petite King Room 7

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 €600
includes taxes & fees
15 Jun - 16 Jun
Northfork Townhouse walk to all

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 €951
includes taxes & fees
25 Jun - 26 Jun
BlackBerry Private home with jacuzzi yearlong

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is €531
includes taxes & fees
15 Jun - 16 Jun
Renovated Townhouse walk to all

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (1 review)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is €1,153
includes taxes & fees
21 Jun - 22 Jun
Minutes from the beach, brand new 3 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

Find out more about Shelter Island Heights

Shelter Island Heights Holiday Homes information

Number of reviews
340
Accommodation
1654 Holiday Homes
Lowest Price
€290
Highest Price
€2,136