Photo by Richard Miska

Search Cottages in Sheffield Island

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Compare 36 Cottages in Sheffield Island with updated reviews, rates, and availability.

Trendy 1 bedroom +loft apartment w/ parking
Dining
Trendy 1 bedroom +loft apartment w/ parking
10.0 out of 10, Exceptional, (1)
"My husband and I are relocating to the East Coast and after a week-long drive across the country, we were happy, tired and grateful to arrive at Leti’s lovely apartment for a 3-week stay. It was exactly what we had hoped for —in fact, better than expected. The unit had parking, a fenced yard (with patio table and grassy area), a washer-dryer (with soap provided!) and a wonderful, well-appointed full kitchen and living space. The apartment was extremely clean with new furnishings and...
Trendy 1 bedroom +loft apartment w/ parking
Cozy Riverside Cottage
Exterior
Cozy Riverside Cottage
10.0 out of 10, Exceptional, (1)
"Cottage is very comfortable and clean. Neighborhood is quiet and in natural surroundings. Be prepared for spotty reception (screenshot access code) but WiFi is excellent in home, so is the TV/music system. Over all, excellent value and great accommodations in a beautiful spot. Only needed it for the weekend, but would book as a destination for some peace and quiet."
Cozy Riverside Cottage
Adorable 1-Bedroom Cottage in Weston, CT
Living-Room view from Mezzanine
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (30)
"Very cozy cottage a little off the beaten path in Weston. Quiet & stocked with amenities for our comfort. The owner was helpful & responsive. If there was any drawback it would be helpful to air out the cottage as its an old building & investing in some new pillows would be appreciated by the next guests. Otherwise a great stay."
The price is AED 716
AED 1,114 total
includes taxes & fees
23 Sep - 24 Sep
Adorable 1-Bedroom Cottage in Weston, CT
Beach house cottage steps to private beach in the heart of Bayville
Beach
Beach house cottage steps to private beach in the heart of Bayville
10.0 out of 10, Exceptional, (8)
"This is my second time here. It is so conveniently located for us being that we have family close by. I will stay here again. Thank you."
Beach house cottage steps to private beach in the heart of Bayville
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Fairfield Cottage · Charming Fairfield Cottage By The Sea
10.0 out of 10, Exceptional, (31)
"What a wonderful find, and only an hour away from NYC. Fairfield CT is beautiful, friendly people, great restaurants, dog friendly, beautiful private beach, the list goes on and on. Thank you to Gerard for being so helpful, kind and always there to answer any questions, and give great recommendations. If you ever need a break from the city, this is the place to go to. Thanks again for such a wonderful holiday! We will be back."
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Beach cottage on private beach!
Beach
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!
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Living area
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
10.0 out of 10, Exceptional, (1)
"Charming cottage, beautiful location, wonderful hosts! Located on a beautiful stretch of river and near outstanding running and hiking.Highly recommend."
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
8.0 out of 10, Very Good, (4)
"The property is in a perfect location to visit Northport on foot and has amazing views of the harbor as you are directly on the water. Main Street of Northport and the main dock and the main park with all its shops is an easy 2 minute walk from the place."
The price is AED 698
AED 999 total
includes taxes & fees
25 Sep - 26 Sep
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Westport "Gold Coast" across from Southport beach
Exterior
Westport "Gold Coast" across from Southport beach
10.0 out of 10, Exceptional, (79)
"Very cute spot in a great location. "
Westport "Gold Coast" across from Southport beach
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Property grounds
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
🔥Fairfield County Cozy cottage , super close great adventure
Interior
🔥Fairfield County Cozy cottage , super close great adventure
9.8 out of 10, Exceptional, (6)
"Comfortable house, not huge, but nicely decorated. Host was very quick to respond when I had trouble with door code. The only con for us was lack of handrails on steps to exterior doors (front and back). Otherwise a great place to stay."
🔥Fairfield County Cozy cottage , super close great adventure
Second floor cottage apartment located in a private community.
Living Room with view towards Bedroom 1
Second floor cottage apartment located in a private community.
9.4 out of 10, Exceptional, (13)
"The cottage was as described and the photos don’t really do it justice, it is lovely and the location cannot be beat. We had good communication with the hosts and overall it was a very nice stay. Would definitely return for a future visit to Stamford!"
Second floor cottage apartment located in a private community.
Beachfront cottage located in the heart of Fairfield Beach!!
Outdoor dining
Beachfront cottage located in the heart of Fairfield Beach!!
9.6 out of 10, Exceptional, (15)
"This is my third year staying at this property. I have friends that live around the area so it is a nice quiet private space to reconnect. Paul the host is always quick to respond to any concerns I may have while staying. My dog Angel is in heaven literally 5 steps to the water . The beach and people are so kind and friendly. Love it!"
Beachfront cottage located in the heart of Fairfield Beach!!
Adirondacks in Westchester
Living area
Adirondacks in Westchester
10.0 out of 10, Exceptional, (1)
"This location is gorgeous! I could just sit on the porch all day and look out at the trees, stream, and lake. It was a perfect get away from 2 days."
Adirondacks in Westchester
California cozy cottage/studio in the middle of the Greenwich
Outdoor dining
California cozy cottage/studio in the middle of the Greenwich
10.0 out of 10, Exceptional, (1)
"This VRBO was a pleasure! Host Olga was very accommodating. This was my first VRBO experience and I will definitely do this again. So much nicer than a hotel stay. It was a wonderful 5 days! I would highly recommend Olga and her California Cottage. "
California cozy cottage/studio in the middle of the Greenwich
Sun and Fun on the beach!!
You are here!
Sun and Fun on the beach!!
9.6 out of 10, Exceptional, (15)
"Very good place on the beach….and beach walking Paul communication was very timely"
Sun and Fun on the beach!!
South Salem Vacation Rental w/ Furnished Deck!
South Salem Vacation Rental | 1BR | 1BA | Stairs Required | 950 Sq Ft
South Salem Vacation Rental w/ Furnished Deck!
10.0 out of 10, Exceptional, (1)
"Everything was easy and fine at the space. I had to stay for family reasons - so "location" was the most important factor to me. The worst thing in the unit is that the spiral stair is narrow - and a fat person or person with bad knees is NOT going to be using that stairwell easily. Otherwise, the unit had everything I needed and was perfectly appointed for an easy weekend stay. Enjoy!"
South Salem Vacation Rental w/ Furnished Deck!
Lakefront/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
Exterior
Lakefront/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
9.0 out of 10, Wonderful, (8)
"Property was exactly as advertised & in a beautiful location. Laurence was a very attentive but unobtrusive host. Recommended."
Lakefront/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Exterior
Charming Mamaroneck Home ~ 22 Mi to Manhattan
3.0 star property
6.0 out of 10, (1)
"Great quiet neighborhood, but this is only part of the home (1st floor, basement, and part of the 2nd floor) and the people upstairs are stepping loudly late into the night. The 3rd bathroom is in the basement with no shower curtain and a shower head that must be held during your entire shower. It was the 1 room that was actually dirty and I cleaned it before we used it. Internet info was inaccurate but provided when we requested. TV instructions lacking. Plenty of room for hanging out and...
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Commack Vacation Rental | 3BR | 1BA | 1,300 Sq Ft | 3 Steps Required for Access
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
8.0 out of 10, Very Good, (3)
"We had family stay here, one set of family left early in the morning and another later. The owner, who lives in the basement, woke up those staying here on their last day at 4:30 in the morning attempting to get in the house thinking we all had left. Scared my family half to death! Check-out time was not honored. Awful stay with nosy owner creeping around everywhere!"
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
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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 Sheffield Island

Stamford Suites
Property amenity
Stamford Suites
2.5 star property
6.8 out of 10, (746)
"It was more than i expected. "
The price is AED 559
AED 626 total
includes taxes & fees
4 Oct - 5 Oct
Stamford Suites
DUNE Fairfield Beach
Room
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (35)
"Enjoyed the stay in the modern suite, located a short walk to the beach. Recommend the hotel and touring in the Fairfield, CT area. "
DUNE Fairfield Beach
Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is AED 283
AED 504 total
includes taxes & fees
6 Oct - 7 Oct
Business or Weekend escape
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

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