Photo by Erisa Dilo

Search Shelter Island Heights Cottage Rentals from CA $161

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Browse Select Shelter Island Heights Cottages

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $161
CA $328 total
includes taxes & fees
Sep 1 - Sep 2
1-bedroom cottage with Grove Beach 🏖️ access.

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (78)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (78)
"This was a great property and close to many things to see and visit. The welcome note and goodies were much appreciated. Great communication from the host!!!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is CA $692
CA $1,356 total
includes taxes & fees
Aug 24 - Aug 25
Southampton cozy cottage by the beach

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (28)
"Cute beach bungalow vibe. The outdoor space, grill, and firepit made this property worthwhile! Lori's a wonderful, accomodating host."
Location and views! Located directly on Shinnecock Bay!

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct

Cozy cottage on Fort Pond Lake.

10.0 out of 10, Exceptional, (16)
"The lake house was a perfect retreat, perfectly located to town, train, trails and beach. We can’t wait to visit again !"
Cozy cottage on Fort Pond Lake.

Pet-friendly Home w/ Hot Tub Near the Hamptons!

3.0 star property
Pet-friendly Home w/ Hot Tub Near the Hamptons!

CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE

10.0 out of 10, Exceptional, (14)
"We had a wonderful stay here while visiting for a wedding. the bedrooms were both upstairs, FYI which I wasn't aware of from the listing but we made it work. The grounds were beautiful and lots of birds to enjoy. "
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (11)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community

Luxury Tiny Home In Niantic

10.0 out of 10, Exceptional, (4)
"This property is perfect for 2-3 guests and located within short distance to town. The house is well built and very clean. Five Stars"
The price is CA $361
CA $628 total
includes taxes & fees
Aug 27 - Aug 28
Luxury Tiny Home In Niantic

Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

9.6 out of 10, Exceptional, (44)
"A lovely beach cottage with bay views and easy walking access to the Atlantic beaches.The place was cozy and clean with expansive open views across reserve land to the bay.A bit tricky to find off the highway at night but we eventually got our bearings!"
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

Direct LI sound waterfront cottage, one level living in Hawks Nest Beach

9.0 out of 10, Wonderful, (2)
"Perfect little beachfront cottage right on the water ...a few steps across your own beach. We had a very relaxing, comfortable visit."
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (72)
"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (115)
"Lovely cottage on the Peconic Bay. We enjoyed our stay; found more than everything we needed. "
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Hidden gem! Southampton beach cottage

10.0 out of 10, Exceptional, (1)
Hidden gem! Southampton beach cottage

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (26)
"Our family stayed at this quaint cottage in the North Fork. The cottage has a nice kitchen, gas fireplace, and well appointed bedrooms. I would love to visit in summer, it must be wonderful!"
Lovely Cottage in the Heart of Long Island Wine country

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
10.0 out of 10, Exceptional, (7)
"My friends and I had a great weekend here. The property is accurately described as listed. It was just enough space for a weekend. There were 3 of us. We used the fold down couch as the 3rd bed which was a good bed. Communication with the host was excellent. The property inside and out was great. We sat outside in the backyard for a while. The walk over the bridge to the Niantic boardwalk wasn’t too long when the weather is good. And we sat outside at Fat Tuna which was within walking distance...
The price is CA $263
CA $521 total
includes taxes & fees
Sep 10 - Sep 11
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shelter Island Heights Hotel Reviews