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Search Vacation Homes in Shelter Island Heights

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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 1951 Vacation Homes in Shelter Island Heights with updated reviews, rates, and availability.

Surf Cottage - Steps from Surf Lodge, Town, and Beach
Beach nearby, beach towels

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
Interior

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
Exterior

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
Fridge, microwave, oven, dishwasher

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
Pool

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
Beach nearby, beach towels

The Cooper-Burke House

10.0 out of 10, Exceptional, (25)
"Nice location and house "
The Cooper-Burke House
Walk to the beach at Black Point, Niantic, Ct.
Beach nearby, sun loungers, beach towels

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
Outdoor dining

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
Smart TV, fireplace, stereo

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
Cozy Westbrook Vacation Rental - Walk to Beach!
Aerial view

Cozy Westbrook Vacation Rental - Walk to Beach!

9.8 out of 10, Exceptional, (19)
"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!
Stunning Waterfront Home with Private Beach!
Aerial view

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!
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
On the beach, sun loungers

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
Outdoor spa tub

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,...
A heated pool

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
Beach nearby, sun loungers, beach towels

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
Terrace/patio

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
Historic Essex Home w/ Large Yard Near Downtown!
TV

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

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

Old meets new in this fully renovated 19th century farm house.
Exquisite New Hampton Home in a Perfect Location
Interior

Exquisite New Hampton Home in a Perfect Location

Exquisite New Hampton Home in a Perfect Location
Charming beach home, complete with pool & cozy guest house!
Interior

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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Other property types in Shelter Island Heights

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1189)
"Nice historical building. Rooms well appointed and a beautiful view."
The price is SAR 675
SAR 845 total
includes taxes & fees
29 May - 30 May
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (378)
"great place to stay"
The price is SAR 549
SAR 668 total
includes taxes & fees
29 May - 30 May
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (284)
"Love the ocean view from the balcony"
The price is SAR 597
SAR 764 total
includes taxes & fees
29 May - 30 May
Windward Shores Ocean Resort
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.