Photo by Tai Bui

Search Cottages in Cheshire

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 57 Cottages in Cheshire with updated reviews, rates, and availability.

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, (54)
"What else can I say about this home it is absolutely beautiful They are sure to have it fully equipped they thought of everything toilet paper to coffee to wine they are the perfect hosts. I brought my dog and they have a nice little patio out in the yard he was able to run around there a little bit and do his thing. Across the street there is the beach and a trail and lighthouse Park is only a few minutes away and that was very nice as well. They are a lovely couple that on the home we are...
Cozy Home near private beach , close to New Haven area colleges Hospitals
Newly renovated cottage on the lake!
Beach

Newly renovated cottage on the lake!

10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!
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
Waterfront Cottage in Branford
Exterior

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford
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, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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, (40)
"Beautiful cottage, spectacular property, wonderful hosts. Not sure what else to say? We came up to CT with our pup to look at areas we may want to move to. The cottage was perfect for us, nice and private and lots of land for our pup to walk. Great state park a few miles away and plenty of good restaurants nearby. Very happy!"
Guest Cottage on Country Estate
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, (8)
"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 detail

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (13)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage
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, (28)
"Tuttles Point is a hidden gem of a neighborhood. I spent my summers as a child in this neighborhood, and I wanted to share my love for this area with my family. This cottage was perfect for what we needed. The view is beautiful and there is so much character in the home that you forget that you might be missing some of our modern comforts. My children loved the rocks out back, the beaches and all the activities in close proximity to this home. If you’re looking for a place to disconnect m,...
1930s Waterfront Cottage on Tuttle's Point
Short Beach Coastal Cottage
Beach

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
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!

9.6 out of 10, Exceptional, (5)
"The house on the lake is clean and very cute. A few things to keep in mind… The stairs to the loft are VERY steep and VERY narrow. So both adults and small children may struggle to get up and down, especially with any type of luggage. There are no closets or dressers for your clothes so maybe bring hangers and a hook for behind the door. Everything else was perfect. "
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Modern, cozy 3 bedroom lakeside cottage
Exterior

Modern, cozy 3 bedroom lakeside cottage

10.0 out of 10, Exceptional, (5)
"Home was beautifully decorated with a warm cozy feel especially in autumn. Perfect for a family reunion in Litchfield and would highly recommend any time of the year!!"
Modern, cozy 3 bedroom lakeside 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
Money Island Home w/ Deck, Kayak & Paddleboards!
Enjoy a getaway unlike any other at this Money Island vacation rental home!

Money Island Home w/ Deck, Kayak & Paddleboards!

10.0 out of 10, Exceptional, (15)
"This waterfront property has it all! A comfortable, well-appointed, modern, light-filled space designed to take full advantage of its location on a point. Sweeping views of the Sound and other Thimbles from a generous deck perfectly positioned for privacy. The nearby sandbar beach feels almost like your own and the sense of friendly community on this small island is evident. The owners are gracious, welcoming, and immediately attentive to every question or need. Cannot recommend more highly!"
Money Island Home w/ Deck, Kayak & Paddleboards!
Charming West Haven Home - Walk to Beach!
Living area

Charming West Haven Home - Walk to Beach!

3.0 star property
Charming West Haven Home - Walk 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.
Don't see what you're looking for?
See all available properties in Cheshire
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is SAR 368
SAR 424 total
includes taxes & fees
24 Nov - 25 Nov
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
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
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
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.

Frequently asked questions

Why book your cottage in Cheshire with Expedia?
Expedia has some superb cottages in Cheshire, so start packing for a memorable stay on nature’s doorstep. If you have a set budget, click on how much you want to spend and the star rating of your property. Or, try out our filters to search for cottages with a pool or a hot tub. We’ll help you find the right digs whatever your style of travel or plans.
How can I find cheap cottages in Cheshire?
An excellent way to compare cheap cottages in Cheshire is with Expedia’s useful filter tool. Refine your search results by amenities, star rating and budget to land unbeatable rates in just a few clicks.