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Compare 192 Cottages in Shelter Island Heights 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
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 $119
$213 total
includes taxes & fees
May 29 - May 30
Shalom Cottage with private beach rights.
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Property grounds
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (54)
"Very clean, beautiful view out back, close to town and beaches, everything you need easily available. Highly recommend."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Property grounds
Waterfront! Charming 4BR Cabin on the Niantic River!
9.6 out of 10, Exceptional, (52)
"The tree outfront needs to be trimmed desperately. Turning out of the house was quite dangerous. The house was cute and old. It was a 15-20 minute drive to all nearby attractions."
Waterfront! Charming 4BR Cabin on the Niantic River!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Exterior
"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 !
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
9.8 out of 10, Exceptional, (59)
"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, 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 $268
$476 total
includes taxes & fees
May 29 - May 30
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
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
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
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
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 $236
$494 total
includes taxes & fees
May 28 - May 29
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Beach nearby
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
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
Southold Cottage w/ Patio & Grill - Walk to Beach!
Southold Cottage w/ Patio & Grill - Walk to Beach!
Fridge, microwave, oven, stovetop
Newly Renovated Beach Cottage in Jamesport, NY with a private beach.
Newly Renovated Beach Cottage in Jamesport, NY with a private beach.
Fridge, microwave, oven, stovetop
Beach Front Cottage-Private Beach
Beach Front Cottage-Private Beach
Interior
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Don't see what you're looking for?
See all available properties in Shelter Island Heights
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 Heights

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is $151
$192 total
includes taxes & fees
May 28 - May 29
Montauk Manor
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (296)
"We enjoyed our stay!"
The price is $169
$203 total
includes taxes & fees
Jun 12 - Jun 13
Montauk Oceanside Suites
Exterior
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $161
$238 total
includes taxes & fees
May 28 - May 29
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 Heights Cottages information

Number of reviews
443
Accommodation
192 Cottages
Lowest Price
$119
Highest Price
$268

Frequently asked questions

How much do cottages in Shelter Island Heights cost?
You can expect to pay between $119 and $268 per night for cottages in Shelter Island Heights. No matter your budget, an ideal stay is just a few clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Shelter Island Heights?
Choose from multiple cottages in Shelter Island Heights with a total average guest review rating of 9.5. Villa Gally - The Ultimate In Hamptons Luxury is an ideal place to relax and unwind between adventures. This 3.5-star cottage also has a barbecue grill and free valet parking services. Villa Charlotte is another top option with travelers visiting this area. It has a 3.5-star rating and amenities including a swimming pool and a firepit.
How many cottages are there in Shelter Island Heights?
Enjoy nature’s beauty in one of the 192 cottages on offer in Shelter Island Heights. To help you reserve your ideal place, click on our handy filters to search for amenities or perks you prefer.
Are there any family-friendly cottages in Shelter Island Heights?
Traveling with your group in Shelter Island Heights is a cinch at Villa Gally - The Ultimate In Hamptons Luxury. With conveniences including a swimming pool and a firepit, you’ll find all the comforts of home at this 3.5-star cottage. Villa Charlotte is another family-friendly option where you and your squad can escape the hustle and bustle of the big city. This cottage has a 3.5-star rating and conveniences including a swimming pool and a picnic area. Once you’ve checked in and dropped off your luggage, there are plenty of family-friendly attractions to explore around Shelter Island Heights. 67 Steps Beach and Orient Beach State Park promise fun for all ages.
Why book your cottage in Shelter Island Heights with Expedia?
Expedia has some excellent cottages in Shelter Island Heights, so get set for a memorable stay close to nature. If you need to stick to a budget, choose how much you’re willing to spend and the star rating of your property. Or, make the most of our filters to search for cottages with a hot tub or free WiFi. We’ll help you find the perfect place whatever your getaway looks like.
How can I find cheap cottages in Shelter Island Heights?
A wonderful way to find cheap cottages in Shelter Island Heights is with Expedia’s convenient filter tool. Narrow your search results by budget, star rating and amenities to take advantage of awesome bargains in a few clicks.
What is there to do in Shelter Island Heights near my cottage?
Whatever you love to do, Shelter Island Heights has plenty to keep you entertained. 67 Steps Beach, Pindar Vineyards and Kontokosta Winery are on most visitors’ itineraries. Don’t miss Raphael Winery, Bedell Cellars and Orient Beach State Park either. With Expedia’s hotel deals in Shelter Island Heights, you’ll be able to discover even more renowned attractions like these with the cash you save.

Recent reviews of Shelter Island Heights hotels
Expedia verified reviews

The Niantic Inn

The Niantic Inn

5/5 Excellent
Excellent hotel!
"Our experience in Niantic and at the Niantic Inn was great! The owner was very friendly and helpful. There was EVERYTHING you could need provided in the clean and comfortable room, with many extras such as bottles of water and snacks. The location of the hotel was better than we imagined as the owner told us about a lovely and scenic 1 mile walk along the boardwalk along the bay, which started right across the street from the Niantic Inn! . She gave suggestions for coffee shops and anything else we asked about. Personal and professional. A delightful stay! Thank you’ "
A verified traveler stayed at The Niantic Inn
Posted 2 days ago
The Niantic Inn