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Search Cottages in Shelter Island

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

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 AED 753
AED 1,450 total
includes taxes & fees
30 Nov - 1 Dec
Beach Bungalow, large porch, 1/2 mile to the water.

Shalom Cottage with private beach rights.

9.0 out of 10, Wonderful, (17)
"The cottage was adorable and beautifully and comfortably furnished and appointed. We had a last-minute change to our reservation and the owner was very helpful in accommodating us, as well as guiding us to the property which was a little tricky to find. We had everything we needed including fresh fruit to our preference. Only wish the bathroom were a little bigger."
The price is AED 338
AED 652 total
includes taxes & fees
3 Dec - 4 Dec
Shalom Cottage with private beach rights.

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

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

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

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.

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

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

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

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

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 Cottage w/ Patio & Grill - Walk to Beach!

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

2.0 star property
"I couldn’t wait to leave a review…to rave about this house. Our hosts met us upon arrival and took the time to show us around. The house was absolutely gorgeous, spacious with state-of-the-art, appliances, tech, and beautifully decorated with attention paid to every detail. It was spa-like. Since the weather was mild for November, they even set up the outdoor patio set and fire pit for us. The house had everything we needed. We know the area so we knew it was conveniently located to shops,...
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

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!

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!

"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

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.

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

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

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1069)
"Property was beautiful, view overlooking the area was great! Parking was convenient and there were charging spots for electric cars! "
The price is AED 537
AED 685 total
includes taxes & fees
2 Dec - 3 Dec
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (338)
"All very good!"
The price is AED 423
AED 520 total
includes taxes & fees
29 Nov - 30 Nov
Montauk Oceanside Suites

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 AED 464
AED 609 total
includes taxes & fees
1 Dec - 2 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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