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Search Cottages in Cheshire

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Compare 56 Cottages in Cheshire with updated reviews, rates, and availability.

Newly renovated cottage on the lake!
Beach
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (18)
"This cabin was perfect for a place to rest and refresh after hiking some of Litchfield area's trails. It was as described by the host and he was very easy to reach with questions. We recommend this cabin as well-located for all that Litchfield county has to offer. "
Newly renovated cottage on the lake!
Guest Cottage on Country Estate
Guest Cottage on 7 acre Estate. Two bedrooms, full bath with a laundry Sleeps 6
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (36)
"the location and size of cottage were just what we were looking for."
Guest Cottage on Country Estate
Waterfront Cottage in Branford
Exterior
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (83)
"We enjoyed our 2nd time at this house. Well-appointed and lots of space for our family to connect. Can’t beat the view!"
Waterfront Cottage in Branford
Guilford Carriage House at Granite Lodge!
Guilford Vacation Rental | 1BR | 1BA | Step-Free Access via Side Door
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (7)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!
Historic Whitneyville Cottage
Exterior
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (12)
"Very convenient for what we needed. Nice little cottage."
Historic Whitneyville Cottage
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
10.0 out of 10, Exceptional, (4)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Cozy 2-bedroom Cottage with Access to Bantam Lake
Cozy 2-bedroom Cottage with Access to Bantam Lake
9.6 out of 10, Exceptional, (17)
"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "
Cozy 2-bedroom Cottage with Access to Bantam Lake
Modern Terryville Cottage w/ Deck & Lake View!
Terryville Vacation Rental | 2BR | 1BA | 800 Sq Ft | 2 Steps to Enter
Modern Terryville Cottage w/ Deck & Lake View!
8.8 out of 10, Excellent, (3)
"The house was in pristine condition. It looked like it was just built and we were the first ones to stay in it. Located not far from stores and restaurants. The owner, (Ron,)was very responsive to any questions we had. We highly recomend this location."
Modern Terryville Cottage w/ Deck & Lake View!
Cozy Country Cottage
Private kitchen
Cozy Country Cottage
2.0 star property
8.8 out of 10, Excellent, (3)
"Get away from the hustle and bustle with this cute country cottage. Queen beds in the first floor and super cool loft, nice updates in the bathroom and kitchen. Window A/C units kept us cool on one of the hottest weeks of the year. Close to Derby and Route 15 made this a super-convenient stop-over for us as we came back from our honeymoon!"
Cozy Country Cottage
The Dream Location for Your Perfect Vacation
Property grounds
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Fall sunsets are a prize possession here at the lake!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (24)
"This is a really lovely and clean home. The owners were very responsive and clearly take great care with the property and rental process. It was very comfortable for me, my mother and my four year old daughter. The lake view is gorgeous and peaceful, however be advised that CT lakes can sometimes get high bacteria levels so it was not swim friendly when we were there "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Private Island Compound with Large Cottage and Guest House
Cut in Two East Island
Private Island Compound with Large Cottage and Guest House
10.0 out of 10, Exceptional, (20)
"The island was the perfect vacation spot for a large family group! We enjoyed the paddle boards and kayaks daily , exploring the ocean and other Thimnle Islamds. We swam off the private beach when the rose was right and off the dock. The gazebo, porches and seating on the rocks were great for reading and boat and bird watching. The single storm was even a unique experience - weather and ocean on all sides! The ferry was convenient - making of island meals possible. E"
Private Island Compound with Large Cottage and Guest House
Cozy Home near private beach , close to New Haven area colleges Hospitals
Property grounds
Cozy Home near private beach , close to New Haven area colleges Hospitals
9.6 out of 10, Exceptional, (51)
"Loved my stay at this cottage! Plenty of space, probably too much space for just me :) Wonderful little touches such as fresh filtered water, bottle of wine etc. Super convenient to the best little beach, which was what I was looking for. Definitely on a busy street though. That would be the only potential down side."
Cozy Home near private beach , close to New Haven area colleges Hospitals
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Welcome to our beach house! Enjoy our huge private backyard w/ tons of amenities
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
9.6 out of 10, Exceptional, (10)
"A/C was started for us, so it was comfortable."
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
Property grounds
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
10.0 out of 10, Exceptional, (2)
"This is a nice spot to enjoy the Long Island Sound."
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
1930s Waterfront Cottage on Tuttle's Point
View of Cottage from Lawn at Waterfront
1930s Waterfront Cottage on Tuttle's Point
9.8 out of 10, Exceptional, (27)
"We loved our time at Little White Top. The house is super clean and has large bedrooms and a really well-stocked kitchen. The big screened porch overlooking the water was a perfect place to play games, eat and just hang out. On calm days we enjoyed kayaking off the beach just down the road. We hope to stay here again!"
1930s Waterfront Cottage on Tuttle's Point
Short Beach Coastal Cottage
Short Beach Coastal Cottage
10.0 out of 10, Exceptional, (14)
"It was really evident that the hosts enjoy this project. Very nice people and everything was tip top."
Short Beach Coastal Cottage
Bright Milford Beach House w/ Outdoor Shower
Living area
Bright Milford Beach House w/ Outdoor Shower
3.0 star property
Bright Milford Beach House w/ Outdoor Shower
Charming Connecticut Retreat Near Museums & Hiking
Living area
Charming Connecticut Retreat Near Museums & Hiking
3.0 star property
Charming Connecticut Retreat Near Museums & Hiking
Wolcott Home w/ Deck: Near Connecticut Attractions
Living area
Wolcott Home w/ Deck: Near Connecticut Attractions
3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
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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 Cheshire

New Haven Village Suites
Front of property
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1925)
"Excellent! Best kept secret in New Haven. My room was spacious. Lobby was beautiful and had coffee and breakfast. I would stay again, but you must have a car."
The price is AED 364
AED 405 total
includes taxes & fees
6 Oct - 7 Oct
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Furnished Apartments by Hyatus Downtown at Yale
Room
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (28)
"Great appartment, well stocked and ready excellent for our trip to visit family "
Luxury Furnished Apartments by Hyatus Downtown at Yale
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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