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Our top choices for Shelter Island vacation 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 ¥21,752
¥66,117 total
includes taxes & fees
Mar 24 - Mar 25
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)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is ¥22,983
¥75,965 total
includes taxes & fees
Mar 30 - Mar 31
Rogers Lake House (87) · CT College+Beach+USCGA

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 ¥22,770
¥81,478 total
includes taxes & fees
Mar 24 - Mar 25
Beachside Bliss w/ Game Room, Gym & Golf Green

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ¥21,018
¥137,038 total
includes taxes & fees
Apr 1 - Apr 2
Black Swan Beachfront Home with Jacuzzi year round

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 ¥19,108
¥44,266 total
includes taxes & fees
Mar 24 - Mar 25
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 ¥35,500
¥79,793 total
includes taxes & fees
Apr 8 - Apr 9
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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 ¥26,910
¥41,115 total
includes taxes & fees
Mar 24 - Mar 25
American Beech in Greenport - Petite King Room 7

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)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is ¥19,108
¥44,720 total
includes taxes & fees
Apr 15 - Apr 16
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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 ¥37,833
¥123,664 total
includes taxes & fees
Apr 1 - Apr 2
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

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 ¥16,560
¥109,407 total
includes taxes & fees
Mar 25 - Mar 26
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.
Coastal New England Waterfront Home, Harkness Park, Casinos

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 ¥40,842
¥88,506 total
includes taxes & fees
Mar 24 - Mar 25
Renovated Townhouse walk to all

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 ¥21,018
¥140,878 total
includes taxes & fees
Mar 29 - Mar 30
Villa Luz Cozy Family Home with Jacuzzi year round

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is ¥82,402
¥167,823 total
includes taxes & fees
Mar 24 - Mar 25
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

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 ¥38,693
¥84,777 total
includes taxes & fees
Mar 24 - Mar 25
Northfork Townhouse walk to all

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 ¥71,654
¥176,645 total
includes taxes & fees
Mar 25 - Mar 26
Minutes from the beach, brand new 4 bedroom

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is ¥237,890
¥310,539 total
includes taxes & fees
Mar 24 - Mar 25
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 ¥429,921
¥868,487 total
includes taxes & fees
Mar 24 - Mar 25
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

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 ¥86,701
¥154,359 total
includes taxes & fees
Mar 24 - Mar 25
Beachfront Greenport Villa

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 ¥214,961
¥363,658 total
includes taxes & fees
Mar 25 - Mar 26
Sag Harbor Water View w Dock 1.5ml from town
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 Hotel Reviews

Find out more about Shelter Island

Shelter Island Vacation Homes information

Number of reviews
241
Accommodation
1793 Vacation Homes
Lowest Price
¥41,115
Highest Price
¥868,487