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Shelter Island Vacation Rentals

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Browse Select Shelter Island Vacation Homes

Our top choices for Shelter Island vacation homes

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is CA $443
CA $824 total
includes taxes & fees
Aug 27 - Aug 28
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Direct waterfront vacation rental, family friendly, pets allowed

10.0 out of 10, Exceptional, (71)
"This was our third time renting and we had an excellent stay yet again. We are booked up for next year already!"
Direct waterfront vacation rental, family friendly, pets allowed

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (69)
"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "
Stunning Hampton Holiday Family Fantasy for your Team

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

10.0 out of 10, Exceptional, (6)
"The is great!!! Very convenient location and plenty to do."
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

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

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

10.0 out of 10, Exceptional, (2)
"The aptly named Charming East Hampton Cottage was a beautiful oasis with lush gardens and comfortable accommodations. The host was very gracious and friendly and communicated with us as soon as we booked the home. My only regret was that we couldnt stay longer."
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

Exquisite New Hampton Home in a Perfect Location

10.0 out of 10, Exceptional, (4)
"Awesome modern home in quiet neighborhood, with beautiful open kitchen and comfortable bedrooms and bathrooms. The outdoor decks and pool were great for lounging and relaxing. The owners were very attentive with communication and the check in process seamless. All around great experience. "
Exquisite New Hampton Home in a Perfect Location

Chic Coastal Cottage In Hither Hills, Montauk. Private Ocean Access

10.0 out of 10, Exceptional, (56)
"The house and location was perfect for our trip!"
Chic Coastal Cottage In Hither Hills, Montauk. Private Ocean Access

The Cooper-Burke House

10.0 out of 10, Exceptional, (27)
"Nice property, conveniently located, great host!"
The Cooper-Burke House

Another rental season is coming up.

10.0 out of 10, Exceptional, (19)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

9.0 out of 10, Wonderful, (2)
"Perfect location."
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

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

9.8 out of 10, Exceptional, (31)
"It was very comfortable and cozy, a very great place to spend with your loved ones, very spacious and had everything we needed to enjoy our stay."
Charming beach home, complete with pool & cozy guest house!

Brand New Beach House In Amagansett

Brand New Beach House In Amagansett

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (71)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !

Hamptons Retreat

Hamptons Retreat

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (2)
"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)."
The price is CA $265
CA $639 total
includes taxes & fees
Aug 26 - Aug 27
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is CA $1,112
CA $1,997 total
includes taxes & fees
Sep 14 - Sep 15
Work and Play Special! Extended Stay Discount
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