Search Shelter Island Cottages

Most properties are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

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

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
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
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
Save an average of 15% on thousands of hotels when you're signed in
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
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
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
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 Bay Cottage · Rocky Neck Park, Beach & Niantic
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 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!
Coffee/tea maker
Charming Old Lyme Cottage, Steps to Private Beach!
10.0 out of 10, Exceptional, (1)
Charming Old Lyme Cottage, Steps to Private Beach!
Fridge, microwave, oven, stovetop
Walk to Love Lane! Immaculately renovated private cottage.
10.0 out of 10, Exceptional, (8)
"The property is lovely and the amenities are absolutely terrific. The owner was very nice - communication was excellent. The area is charming. I can’t say enough great things about how pleased we were with the cottage and the garage which is a clean and well equipped game/workout space. So looking forward to renting again next Christmas"
Walk to Love Lane! Immaculately renovated private cottage.
Property grounds
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (8)
"Everything was exactly as described. The host was accessible for questions during the stay. All went great!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior
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
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
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, (1019)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is $168
$211 total
includes taxes & fees
20 May - 21 May
Montauk Manor
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (295)
"We enjoyed our stay!"
The price is $156
$188 total
includes taxes & fees
22 May - 23 May
Montauk Oceanside Suites
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
613
Accommodation
163 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Shelter Island with Expedia?
We think that a vacay should be hassle-free, so if you’re after cottages in Shelter Island at a competitive price, Expedia has your back. Keep costs down and pick an economical option surrounded by nature, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Shelter Island?
The easiest way to locate cheap cottages in Shelter Island is with Expedia’s handy filter tool. Narrow down your search results by amenities, star rating and budget to access awesome rates in a couple of clicks.

Recent reviews of Shelter Island hotels
Expedia 亿客行 verified reviews