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Search Vacation Homes in Shelter Island Heights

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Compare 2106 Vacation Homes in Shelter Island Heights with updated reviews, rates, and availability.

Surf Cottage - Steps from Surf Lodge, Town, and Beach

9.6 out of 10, Exceptional, (72)
"Our home away from home"
Surf Cottage - Steps from Surf Lodge, Town, and Beach

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

10.0 out of 10, Exceptional, (58)
" Beautiful property one block from the beach— very well thought out with everything you need for a great beach vacation. "
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (24)
"Had a wonderful stay. The house was large enough to allow us all to have our own rooms. Location was perfect and within walking distance of everything. "
Large Charming Historic House close to Beaches

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

10.0 out of 10, Exceptional, (1)
"Great location to see all the eastern LI towns. The house is well appointed and nicely decorated. Easy communication with the host. "
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

The Cooper-Burke House

10.0 out of 10, Exceptional, (26)
"Nice location and house "
The Cooper-Burke House

Walk to the beach at Black Point, Niantic, Ct.

10.0 out of 10, Exceptional, (92)
"We had an amazing stay. This was the perfect weekend trip for us with our pups to celebrate our husky's 10th birthday(he has terminal cancer and we werent sure we would be celebrating this milestone with him). House was very clean and welcoming. Beach is just a short walk (or drive in the cold). The kids loved the ping pong table and being able to walk down to the beach. Host was easy to get ahold of if needed. Would definitely stay again."
Walk to the beach at Black Point, Niantic, Ct.

Charming Blue House • Ocean Views in Westbrook

10.0 out of 10, Exceptional, (4)
"Our family loved our 3 day stay. Property and host were great. "
Charming Blue House • Ocean Views in Westbrook

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (84)
"Rick was a gracious host; the house was clean, and the beach was nearby. We enjoyed our stay "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

2.0 out of 10, (1)
"upon arrival to the house, they did not give us clear information as to which floor we were staying on. They gave us the information for both the first floor and the second floor without telling us which floor was ours. Then after checking in, we asked for the Wi-Fi password and had some other questions to which they did not respond or answer ever. At the end of our stay, they contacted Verbo directly and tried to charge me an additional 730. Safe to say I will never be booking with them again."
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Stunning Waterfront Home with Private Beach!

10.0 out of 10, Exceptional, (43)
"The property is immaculate, so clean and peaceful, views are stunning. Can’t recommend enough."
Stunning Waterfront Home with Private Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

9.8 out of 10, Exceptional, (20)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

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

10.0 out of 10, Exceptional, (19)
""Waterfront beauty in Niantic, CT.Ocean views, peaceful great place "
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (7)
"Robert was an amazing host..We had an incredible New Year’s Eve…We are already planning our next trip back… "
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Newly built ranch, beautifully landscaped with pool, large yard, patio,...

10.0 out of 10, Exceptional, (19)
"This property was gorgeous! It’s conveniently located right in the heart of Greenport and the nearby private beach was stunning! Highly recommend this location, can only imagine how perfect it’d be for the summer time!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (56)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

The SandPiper

9.8 out of 10, Exceptional, (21)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper

Old meets new in this fully renovated 19th century farm house.

Old meets new in this fully renovated 19th century farm house.

Historic Essex Home w/ Large Yard Near Downtown!

10.0 out of 10, Exceptional, (48)
"Everything was great! Perfect writing retreat"
Historic Essex Home w/ Large Yard Near Downtown!

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (25)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!
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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