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Search Cottages in Sheffield Island

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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Cottages in Sheffield Island

Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (40)
"beautiful cottage with all the amenities you need.. charming historic property.. would highly recommend "
Adorable 1-Bedroom Cottage in Weston, CT
Beachfront cottage located in the heart of Fairfield Beach!!
On the beach

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (15)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Fridge, microwave, stovetop, dishwasher

Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

7.8 out of 10, Good, (6)
"We felt very cozy in the home. We were comfortable letting our dogs run around the back yard. Excellent location to all our favorite places. We will stay again. "
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (86)
"Had the best time. Walked to the beach. Great local restaurants as well."
Westport "Gold Coast" across from Southport beach
Second floor cottage apartment located in a private community.
Miscellaneous

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"What a lovely apartment hidden away on a private street. It is very clean and well-kept, and extra attention is given to making sure guests have what they need. Communication with hosts was easy and straightforward. We were very pleased with our stay. "
Second floor cottage apartment located in a private community.
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (10)
"We really enjoyed this place and location. Everything as advertised. Clean, safe area with great parking, convenient to 95 and all of Stamford, comfortable bed, W/D steps away. "
Trendy 1 bedroom +loft apartment w/ parking
Beach house cottage steps to private beach in the heart of Bayville
Interior

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (9)
"Very cute house within walking distance to the beach and restaurants. Great place to stay when we visited daughter at LIU!"
Beach house cottage steps to private beach in the heart of Bayville
Beach cottage on private beach!
Beach nearby, sun loungers, beach towels

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington

10.0 out of 10, Exceptional, (2)
"We stayed here for a hockey tournament, very nice and cozy!"
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Terrace/patio

Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC

9.0 out of 10, Wonderful, (7)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
South Salem Vacation Rental w/ Furnished Deck!
Miscellaneous

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!
Charming 2 Bedroom Cottage in Peaceful New Canaan
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan
Cozy Riverside Cottage
Outdoor dining

Cozy Riverside Cottage

10.0 out of 10, Exceptional, (3)
"Check-in was very simple. The neighborhood very quiet and walkable along the bay. All the amenities were available plus extras. The host was super and always reachable, much appreciated. We plan on staying again soon!!"
Cozy Riverside Cottage
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Dining

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (31)
"Gerard was very responsive and helpful and the rental was lovely and in a great location. The beach access was great as were the beach accessories we could borrow! The house stayed nice and cool in during the hot days! Would stay again."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Exterior

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

10.0 out of 10, Exceptional, (9)
"Wonderful stay!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Smart TV, computer monitors, printers

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"I spent 2 serene weeks here and hope to return some day! With modern creature comforts in the kitchen, the rest of this home is very rustic. If you are looking for peace and quiet, and are into drawing, cooking or reading books to the sounds of trees rustling and water flowing across the street, you will be in heaven here. For summer months, note that there is only a small portable AC unit in the sunroom. There are several fans and it was manageable in early summer, but I imagine it is quite...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Sun and Fun on the beach!!
TV

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (15)
"Perfect beach and outdoor life for young kids! Such a great relaxing long weekend - the house had everything we needed. Hoping for another stay soon!"
Sun and Fun on the beach!!
Ridgefield Cottage: Walk to Town & Movie Theater!
Fridge, microwave, oven, stovetop

Ridgefield Cottage: Walk to Town & Movie Theater!

Ridgefield Cottage: Walk to Town & Movie Theater!
Charming 1-bedroom Stony Brook cottage -walking distance to village & university
Microwave, dishwasher

Charming 1-bedroom Stony Brook cottage -walking distance to village & university

Charming 1-bedroom Stony Brook cottage -walking distance to village & university
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Terrace/patio

Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

3.0 star property
Quiet Commack Cottage w/ Pool, 8 Mi to 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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Frequently asked questions

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