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Compare 183 Cottages in Shelter Island Heights with updated reviews, rates, and availability.

Beach Bungalow, large porch, 1/2 mile to the water.
Exterior

Beach Bungalow, large porch, 1/2 mile to the water.

8.4 out of 10, Very Good, (5)
"Very nice and comfortable property "
Beach Bungalow, large porch, 1/2 mile to the water.
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Exterior detail

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (20)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is SAR 409
SAR 719 total
includes taxes & fees
3 Jan - 4 January 2025
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds
Exterior

Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds
Waterfront! Charming 4BR Cottage on the Niantic River!
Exterior

Waterfront! Charming 4BR Cottage on the Niantic River!

9.6 out of 10, Exceptional, (59)
"We loved the antique house filled with family treasures. We spent many peaceful hours by the firepit looking over the river. The location is great, close to restaurants and stores. Amy is a wonderful host, checking in with us to make sure everything was okay. Thank you Amy. "
Waterfront! Charming 4BR Cottage on the Niantic River!
Fabulous Waterfront Property in the Heart of Wine Country
Waterfront Views overlooking Gold smith inlet. Great for fishing and kayaking.

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (171)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country
Pace's Place Close to North Fork Vineyards
Exterior

Pace's Place Close to North Fork Vineyards

10.0 out of 10, Exceptional, (36)
"If you’re looking for a quick visit to the winery’s this is the perfect place. Beautifully decorated, very responsive host and location is ideal!"
Pace's Place Close to North Fork Vineyards
Walk to Love Lane! Immaculately renovated private cottage.
Exterior

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (14)
"Great private location. Awesome if you have a dog. Easy to get to everything."
Walk to Love Lane! Immaculately renovated private cottage.
Beach access Cozy Cottage
Interior

Beach access Cozy Cottage

9.8 out of 10, Exceptional, (6)
"Very clean and adorable place providing all one needs for peace and respite. I would return again."
Beach access Cozy Cottage
Charming and Bright Cottage with Salt Water Pool
Pool

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (5)
"My husband and I stayed here for a weekend in September and loved every minute. Cottage was well decorated, very clean and had everything you would need. We loved the outdoor shower and the host was so accommodating and thoughtful. Highly recommend and hope to return soon. "
Charming and Bright Cottage with Salt Water Pool
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Exterior

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Southold Cottage w/ Patio & Grill - Walk to Beach!
Southold Vacation Rental | 2BR | 1BA | 2 Steps Required | 440 Sq Ft

Southold Cottage w/ Patio & Grill - Walk to Beach!

Southold Cottage w/ Patio & Grill - Walk to Beach!
Town walking distance-Bridgehampton Cottage
Living area

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Great last minute stay with our pup. House offered ability to have our dog and a back yard for him to play."
Town walking distance-Bridgehampton Cottage
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays
Living area

Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent Host, great stay, beautiful property and set up and very modern."
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays
70 Year old cottage on 2.8 acres, stunning views and sunsets
Miscellaneous

70 Year old cottage on 2.8 acres, stunning views and sunsets

8.4 out of 10, Very Good, (6)
"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"
70 Year old cottage on 2.8 acres, stunning views and sunsets
Location and views! Located directly on Shinnecock Bay!
Property grounds

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (22)
"We enjoyed our stay. The location was great and the owner was available for questions. "
Location and views! Located directly on Shinnecock Bay!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (105)
"Lovely rental; very easy to work with property manager. Clean, close to ocean - would rent again"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
"Salt 'n' Lyme" - Walk to everything !
Property grounds

"Salt 'n' Lyme" - Walk to everything !

9.4 out of 10, Exceptional, (29)
"Nice place in quiet neighborhood with great owner. "
"Salt 'n' Lyme" - Walk to everything !
Enchanted Waterfront Cottage
Beach

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Classic Cottage in Best Private Community in Old Lyme CT.
Recent exterior renovations

Classic Cottage in Best Private Community in Old Lyme CT.

10.0 out of 10, Exceptional, (26)
"A wonderful cottage in a great community at Point O Woods Beach. The host was incredibly helpful, responsive and did everything to make our stay a memorable one. Thank you so much!"
Classic Cottage in Best Private Community in Old Lyme CT.
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Private kitchen

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (24)
"A five star review is not enough for this beautiful property! It is so well appointed, with everything you can possibly imagine to make your stay nothing less than perfect! It is an immaculate place that is decorated beautifully and the moment you open the door here you know you’ve chosen a charming and beautiful place to stay. The owner, Bill, was readily available prior to arriving to answer any questions we had. Even after we were here, he was in communication with us, which is always a...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
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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Other property types in Shelter Island Heights

Montauk Manor
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1084)
"Clean, spacious and very comfy with beautiful views! Can’t wait to stay again in the future "
The price is SAR 648
SAR 813 total
includes taxes & fees
24 Dec - 25 Dec
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (347)
"Needs to have someone man the phones…"
The price is SAR 483
SAR 588 total
includes taxes & fees
30 Dec - 31 Dec
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is SAR 474
SAR 623 total
includes taxes & fees
5 Jan - 6 January 2025
Windward Shores Ocean Resort
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.

Frequently asked questions

How much do cottages in Shelter Island Heights cost?
Cottages in Shelter Island Heights range between SAR 409 and SAR 409 per night. These properties offer a chance to get in tune with nature — at a price you can afford. These prices were 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.
How many cottages are there in Shelter Island Heights?
Stay in touch with nature in one of the 183 cottages waiting for you in Shelter Island Heights. To help you select a place that’s right for you, make use of our handy filters to search for perks or amenities you need.
Why book your cottage in Shelter Island Heights with Expedia?
Booking a cottage in Shelter Island Heights is as easy as working out your travel dates and selecting your ideal place for a vacation in nature. From high-end retreats to low-cost properties and cottages that feature perks like free WiFi, Expedia has something for all tastes. As for epic deals? We’ve have them as well!
How can I find cheap cottages in Shelter Island Heights?
An excellent way to compare cheap cottages in Shelter Island Heights is with Expedia’s user-friendly filter tool. Narrow your search results by budget, star rating and amenities to secure excellent rates in a couple of clicks.