Search Cottages in Shelter Island

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

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
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)."
Shalom Cottage with private beach rights.
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
9.4 out of 10, Exceptional, (30)
"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 AED 1,043
AED 1,824 total
includes taxes & fees
4 Jun - 5 Jun
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
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Sabbatical a Private guest cottage in Sag Harbor
9.0 out of 10, Wonderful, (4)
"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
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
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
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (55)
"The cottage was quite wonderful with a large kitchen and comfy porched living-room. Scott was very quick regarding any communication. The only thing in the description that I would add is that " you'll need to bring your own towels and bed linens". It wasn't a problem, but our airplane carry-on bags only were already packed. We made our adjustments and ended up checking a bag, no worries. Just a thought. We thoroughly enjoyed its quiet and relaxing location."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Charming Old Lyme Cottage, Steps to Private Beach!
7.4 out of 10, Good, (3)
"Very intimate cottage setting, lovely beach scenery, walking distance to the beach, feet away from hearing the crash of the waves. Short drive to grab whatever you have forgotten or need to enhance your stay in this tiny home. Great location to unplug, energize, and bond with your family. You can create the quality time you miss out on in the world today, you will not have the distractions of television, internet, or gaming."
Charming Old Lyme Cottage, Steps to Private Beach!
Walk to Breakwater Beach in Heart of Wine Country
9.8 out of 10, Exceptional, (7)
"Lovely place to stay beautiful location. Carl was super responsive and accommodating. Thank you!"
Walk to Breakwater Beach in Heart of Wine Country
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
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 AED 852
AED 1,787 total
includes taxes & fees
2 Jun - 3 Jun
The Bay Cottage · Rocky Neck Park, Beach & Niantic
"Salt 'n' Lyme" - Walk to everything !
9.4 out of 10, Exceptional, (20)
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Waterfront Cottage w/ Sunroom + Patio & Grill
6.8 out of 10, (3)
"Relaxing and beautiful sunset views , Clean and floor plan one floor plan was perfect ! Spacious and so nice to relax on this vacation ! Close to everything we needed !"
Waterfront Cottage w/ Sunroom + Patio & Grill
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (61)
"This cozy property may seem small but it is organized with care to provide all that you might need. The kitchen is well equipped and the place is full of welcome touches including a generous snack basket, coffee, sugar, and half and half. The deck is a great place to sit and listen to the birds and enjoy being outdoors. The location is convenient to all the destinations along that part of the shore, and there are many nearby restaurants and grocery stores. Jaime was extremely responsive and...
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Walk to Love Lane! Immaculately renovated private cottage.
10.0 out of 10, Exceptional, (9)
"This is beautiful cottage, and the location is perfect for all the vineyards. The house was VERY clean, and the garage is a great place to hang out and relax too. My Husband and I will be booking again very soon for another getaway. Thank you so much."
Walk to Love Lane! Immaculately renovated private cottage.
Charming Old Saybrook Cottage < 1 Mi to Beach
10.0 out of 10, Exceptional, (15)
"Pleasant !"
Charming Old Saybrook Cottage < 1 Mi to 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
Cozy cottage on Fort Pond Lake.
10.0 out of 10, Exceptional, (5)
"Cute little house on the lake, very close to town Very peaceful."
Cozy cottage on Fort Pond Lake.
Beach Bungalow, large porch, 1/2 mile to the water.
The price is AED 735
AED 1,425 total
includes taxes & fees
2 Jun - 3 Jun
Beach Bungalow, large porch, 1/2 mile to the water.
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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

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1023)
"Best affordable hotel in Montauk"
The price is AED 1,098
AED 1,325 total
includes taxes & fees
4 Jun - 5 Jun
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (237)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is AED 887
AED 1,092 total
includes taxes & fees
9 Jun - 10 Jun
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"Very nice location and nice condo"
The price is AED 864
AED 1,185 total
includes taxes & fees
17 Jun - 18 Jun
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.

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