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Compare 163 Cottages in Shelter Island with updated reviews, rates, and availability.

Exterior
Sabbatical a Private guest cottage in Sag Harbor
10.0 out of 10, Exceptional, (3)
"Beautiful studio apartment and truly a retreat from our busy work schedules. Nice response from host when we had questions. Lovely location and truly inspiring..."
Sabbatical a Private guest cottage in Sag Harbor
Outdoor pool
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (47)
"Eunyoung and Mark have a beautiful home and have created the best “home away from home” for travelers. We thoroughly enjoyed our stay and look forward to returning next summer!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (52)
"Great place to stay! The house was very clean and well stocked in the kitchen. Made it very easy to cook meals. Our family and two small children had a great time. The hosts had great communication and made sure we had everything we needed! Would definitely book again!"
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
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Fridge, microwave, oven, stovetop
Fabulous Waterfront Property in the Heart of Wine Country
10.0 out of 10, Exceptional, (153)
"Lovely home! Beautiful view! House has everything you need."
Fabulous Waterfront Property in the Heart of Wine Country
Exterior
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (58)
"What an absolute Gem of a VRBO rental! My son & his future wife own a home in Madison so the Clinton area was perfect for our stay. Jamie was a wonderful host providing snacks, soda and coffee during our stay. The unit was spotless, and our one question was responded to quickly. We’ll definitely be back - actually in June for the wedding. Thank you Jamie for the hospitality!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Fridge, microwave, stovetop, dishwasher
Charming Old Saybrook Cottage < 1 Mi to Beach
10.0 out of 10, Exceptional, (14)
"Pleasant !"
Charming Old Saybrook Cottage < 1 Mi to Beach
3 bedrooms, desk, iron/ironing board, WiFi
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, (5)
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is $239
$497 total
includes taxes & fees
May 20 - May 21
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Beach
Beach access Cozy Cottage
10.0 out of 10, Exceptional, (3)
"My friends and I had a great time staying at this adorable cottage! The beach is so close and the parking pass is a lifesaver! We also loved making a fire and relaxing in the backyard. There was plenty of room in the kitchen to cook while spending time together. Will definitely book again!"
Beach access Cozy Cottage
Beach nearby, sun loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (88)
"Positive experience, great location, and cozy accommodations for a centrally located family weekend."
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Property grounds
Classic Cottage in Best Private Community in Old Lyme CT.
10.0 out of 10, Exceptional, (25)
"Great trip! We could hear the ocean from the cottage and the view of the beach was beautiful. We played tennis, basketball, hiked, rode bikes and took many walks around the community. The cottage had everything we needed and the grill was great too."
Classic Cottage in Best Private Community in Old Lyme CT.
Beach nearby, sun loungers, beach towels
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
10.0 out of 10, Exceptional, (15)
"Comfortable, well appointed home. Beds were comfortable. Everything was super clean. We were very pleased with our stay and would definitely return."
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach nearby
The Old Salt Cottage · Cozy Gateway Near Beach
10.0 out of 10, Exceptional, (4)
"The house looks so cute and cozy, but when you walked in and around, the house was up to date and spacious. All amenities and necessaries were provided for a wonderful stay, albeit way too short for such a lovely place."
The price is $330
$707 total
includes taxes & fees
May 19 - May 20
The Old Salt Cottage · Cozy Gateway Near Beach
A beach cottage gem...
10.0 out of 10, Exceptional, (57)
"We enjoyed this private spot right on the water and the cozy cottage that had everything we needed."
A beach cottage gem...
Fridge, microwave, oven, stovetop
Pace's Place Close to North Fork Vineyards
10.0 out of 10, Exceptional, (33)
"Another great stay in Cutchogue. Our 6th year visiting the north fork and we couldn’t be happier with our accommodations and host!"
Pace's Place Close to North Fork Vineyards
Fridge, microwave, stovetop, dishwasher
Hamptons Vacation Rental w/ Seasonal Pool!
10.0 out of 10, Exceptional, (2)
"We went to Long Island for an event and this house provided us with a very comfortable place to stay! The house was clean and well supplied; the deck and yard lovely and provided nice privacy. There is a pool which is quite nice but we did not use it. We highly recommend this rental!"
Hamptons Vacation Rental w/ Seasonal Pool!
On the beach
Peconic Sound Beach Home: Backyard & Vineyards
9.8 out of 10, Exceptional, (6)
"Tucked away near the sound….a piece of paradise ! Truly a beautiful place to unwind and enjoy all the North Fork has to offer . Centrally located on the North Fork, but easy access to a spectacular beach . You will leave refreshed & trying to figure out how soon you can return ."
Peconic Sound Beach Home: Backyard & Vineyards
Beach nearby
Walk to Breakwater Beach in Heart of Wine Country
9.8 out of 10, Exceptional, (6)
"Lovely place to stay beautiful location. Carl was super responsive and accommodating. Thank you!"
Walk to Breakwater Beach in Heart of Wine Country
Fridge, microwave, oven, stovetop
Cozy Cottage on the North Fork Close to Vineyards & Beaches
9.8 out of 10, Exceptional, (33)
"Perfect place to stay for the weekend! We had a lovely time. The cottage was adorable in the host was very helpful."
Cozy Cottage on the North Fork Close to Vineyards & Beaches
Fridge, microwave, oven, stovetop
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
9.6 out of 10, Exceptional, (28)
"The home was very much as described in the VRBO listing, the booking process was secure, arrival, check-in and checkout were well coordinated, communication with some delay, regarding nonworking cable TV, otherwise excellent experience."
The price is $286
$499 total
includes taxes & fees
May 21 - May 22
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
Interior
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is $109
$199 total
includes taxes & fees
May 19 - May 20
Shalom Cottage with private beach rights.
Don't see what you're looking for?
See all available properties in Shelter Island
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.

Other property types in Shelter Island

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is $168
$211 total
includes taxes & fees
May 20 - May 21
Montauk Manor
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (235)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is $154
$197 total
includes taxes & fees
May 19 - May 20
Windward Shores Ocean Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $224
$310 total
includes taxes & fees
Jun 9 - Jun 10
The Surf Club
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.

Shelter Island Cottages information

Number of reviews
515
Accommodation
163 Cottages
Lowest Price
$109
Highest Price
$286

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