Holiday Homes in Shelter Island Heights

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Our top choices for Shelter Island Heights holiday homes

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)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is AU$533
includes taxes & fees
18 Mar - 19 Mar
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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)
"Communication was excellent. "
United States
Katy C.
The price is AU$686
includes taxes & fees
30 Mar - 31 Mar
Rogers Lake House (87) · CT College+Beach+USCGA

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 AU$376
includes taxes & fees
18 Mar - 19 Mar
American Beech in Greenport - Petite King Room 7

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 AU$379
includes taxes & fees
19 Mar - 20 Mar
Stylish Modern Stay Steps from the Ocean

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 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 AU$509
includes taxes & fees
22 Mar - 23 Mar
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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 AU$765
includes taxes & fees
18 Mar - 19 Mar
Beachside Bliss w/ Game Room, Gym & Golf Green

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (53 reviews)
"Pet friendly, good communication with host, great location and friendly neighborhood. Comfortable cottage. "
United States
Ed F.
The price is AU$405
includes taxes & fees
13 Apr - 14 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"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 AU$825
includes taxes & fees
18 Mar - 19 Mar
Renovated Townhouse walk to all

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 AU$882
includes taxes & fees
18 Mar - 19 Mar
Northfork Townhouse walk to all

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
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 AU$1,562
includes taxes & fees
23 Mar - 24 Mar
Black Swan Beachfront Home with Jacuzzi year round

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 AU$1,106
includes taxes & fees
1 Apr - 2 Apr
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

Black Point Bungalow Near Downtown Niantic

Black Point Bungalow Near Downtown Niantic
East Lyme
9.4 out of 10, Exceptional, (3 reviews)
"Cutest little place ever. All newly renovated."
United States
Michael S.
The price is AU$593
includes taxes & fees
31 Mar - 1 Apr
Black Point Bungalow Near Downtown Niantic

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 AU$1,010
includes taxes & fees
26 Mar - 27 Mar
BlackBerry Private home with jacuzzi yearlong

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 AU$870
includes taxes & fees
19 Mar - 20 Mar
Coastal New England Waterfront Home, Harkness Park, Casinos

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is AU$1,538
includes taxes & fees
26 Mar - 27 Mar
Minutes from the beach, brand new 4 bedroom

Villa Luz Cozy Family Home with Jacuzzi year round

Villa Luz Cozy Family Home with Jacuzzi year round
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 AU$1,227
includes taxes & fees
29 Mar - 30 Mar
Villa Luz Cozy Family Home with Jacuzzi year round

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is AU$1,413
includes taxes & fees
18 Mar - 19 Mar
Beachfront Greenport Villa

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is AU$2,694
includes taxes & fees
19 Mar - 20 Mar
Cozy 5 Bedroom With Wi-fi And Air Condition

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
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 AU$7,518
includes taxes & fees
18 Mar - 19 Mar
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
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

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Shelter Island Heights Holiday Homes information

Number of reviews
232
Accommodation
1814 Holiday Homes
Lowest Price
AU$376
Highest Price
AU$7,518