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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

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, (42)
"Loved our stay. We'll be back I am sure."
The price is AED 716
AED 1,092 total
includes taxes & fees
31 Jul - 1 Aug
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!!
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 comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (89)
"Very cute spot in a great location. "
Westport "Gold Coast" across from Southport beach
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Fridge, microwave, stovetop, dishwasher

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

7.6 out of 10, Good, (7)
"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!
Second floor cottage apartment located in a private community.
Smart TV

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"This was a great property - location was perfect and the hosts were so easy to communicate with. It was exactly as pictured and was a great stay!"
Second floor cottage apartment located in a private community.
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, (3)
"Brand new, state-of-the art temperature control system; spacious, private little cottage. Large kitchen area with dining room, pleasant tv room; located minutes from the village of Huntington. Large bathroom located on ground floor, bedrooms upstairs. A chill host, who did not get angry at me for locking myself out, very kind. Felt very welcome there, no fuss, easy-peasy. I would gladly rent that property again."
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
House (3 Bedrooms) | Interior

Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!

3.0 star property
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
Charming 1 bedroom Stony Brook cottage -walking distance to village & university
Microwave, dishwasher

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

10.0 out of 10, Exceptional, (3)
"Loved the property. Clean small space. Perfect for a couple! "
Charming 1 bedroom Stony Brook cottage -walking distance to village & university
South Salem Vacation Rental w/ Furnished Deck!
Fridge, microwave, stovetop, dishwasher

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
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"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)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
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, fireplace, computer monitors, printers

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Sun and Fun on the beach!!
Dining

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (16)
"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!
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

Why book your cottage in Sheffield Island with Expedia?
Reserving a cottage in Sheffield Island is as simple as deciding on your travel dates and picking your ideal place for a vacation in the outdoors. From high-end retreats to affordable properties and cottages that feature perks like a hot tub, Expedia has something for all styles and tastes. As for unbeatable deals? We've got them as well!
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Expedia is here to help you easily source cheap cottages in Sheffield Island. To discover a fantastic stay in a few quick clicks, try out the filter tool to refine your search by star rating, amenities and budget.