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Compare 181 Cottages in Shelter Island with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Welcome to our cute getaway

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (68)
"We really enjoyed our time away at this wonderful cottage!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
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 "
The price is SAR 770
SAR 1,467 total
includes taxes & fees
30 Nov - 1 Dec
Beach Bungalow, large porch, 1/2 mile to the water.
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
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
Charming Old Saybrook Cottage < 1 Mi to Beach
Old Saybrook Vacation Rental | 4BR | 2BA | Steps Required | 1,400 Sq Ft

Charming Old Saybrook Cottage < 1 Mi to Beach

10.0 out of 10, Exceptional, (23)
"Old Saybrook is a very comfortable, clean, and well kept home. Sizeable bedrooms and baths, comfortable beds, and ample linens provided. Basically, check in using the security code and that's it! We are so happy we chose Old Saybrook for our stay, as it made for a very comfortable, and relaxing trip. We were not there long enough to have enjoyed the back yard grill, but surely would have if we could. BTW...the host is GREAT!!!"
Charming Old Saybrook Cottage < 1 Mi to Beach
Hampton Cottage.
Exterior

Hampton Cottage.

10.0 out of 10, Exceptional, (2)
"Thank you. We enjoyed our stay and the camp fire"
The price is SAR 721
SAR 1,029 total
includes taxes & fees
1 Dec - 2 Dec
Hampton 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
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays
Shalom Cottage with private beach rights.
Exterior detail

Shalom Cottage with private beach rights.

9.0 out of 10, Wonderful, (17)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is SAR 319
SAR 636 total
includes taxes & fees
26 Nov - 27 Nov
Shalom Cottage with private beach rights.
Cozy Cottage on the North Fork Close to Vineyards & Beaches
Terrace/patio

Cozy Cottage on the North Fork Close to Vineyards & Beaches

9.8 out of 10, Exceptional, (36)
"Such a cute cottage and perfect location. We loved the cottage decor and cleanliness. (I’m picky) Wineries and towns were close by and easily accessible. All communication was timely and helpful. Would stay again. "
Cozy Cottage on the North Fork Close to Vineyards & Beaches
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.
White Beach House ope September!
Dining

White Beach House ope September!

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!"
White Beach House ope September!
Lovely Cottage in the Heart of Long Island Wine country
Beautiful and peaceful in all seasons.

Lovely Cottage in the Heart of Long Island Wine country

10.0 out of 10, Exceptional, (21)
"We love coming here-Eileen makes it so easy and we can’t get enough of the overall coziness and warmth of the place. Perfect for a quiet getaway!"
Lovely Cottage in the Heart of Long Island Wine country
Walk to Breakwater Beach in Heart of Wine Country
Exterior

Walk to Breakwater Beach in Heart of Wine Country

9.6 out of 10, Exceptional, (9)
"Very Nice house!. Clean and close to all the wineries. The beach was residents only parking and we did not have a pass. Was not a walk to it either. Maybe could have got a pass for the day, but we got there late and just drove in and out. We found out that a lot of the beaches in North Fork require Resident parking Passes. We really enjoyed our stay and found it very Relaxing.Thank you Carl for a nice home to hang out for a few days.."
Walk to Breakwater Beach in Heart of Wine Country
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
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
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!
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

Montauk Manor
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1069)
"Absolutely everything my girlfriend and I could have asked for. Will be happy to return one day!"
The price is SAR 549
SAR 700 total
includes taxes & fees
26 Nov - 27 Nov
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (338)
"All very good!"
The price is SAR 433
SAR 531 total
includes taxes & fees
26 Nov - 27 Nov
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is SAR 474
SAR 623 total
includes taxes & fees
3 Dec - 4 Dec
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.

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