A stone tower with a metal gate, surrounded by trees and a stone wall.

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Cheshire cottages

A two-story brick house with a white garage door, surrounded by a well-maintained lawn and a tree.

1. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is CA $383
CA $756 total
includes taxes & fees
Dec 6 - Dec 7
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

2. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
The price is CA $180
CA $289 total
includes taxes & fees
Dec 2 - Dec 3
Serene Country Cottage
A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

3. Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (86 reviews)
"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."
United States
Vincent
The price is CA $155
CA $410 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Home near private beach , close to New Haven area colleges Hospitals
Two Adirondack chairs facing a river with a grassy area and trees in the background.

4. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
10.0 out of 10, Exceptional, (1 review)
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
United States
Victoria F.
The price is CA $445
CA $796 total
includes taxes & fees
Nov 8 - Nov 9
Waterfront Lake Cottage - Lake Access -Kayaks
A two-story house with a dock extending into a lake, surrounded by trees with autumn foliage.

5. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is CA $325
CA $637 total
includes taxes & fees
Nov 8 - Nov 9
Escape to Bantam Lake- With Fireplace and Hot tub!
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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Top Cheshire Hotel Reviews

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"I never thought a motel 6 could feel like home, but they’ve done it. The staff is so caring and is always going above and beyond to ensure my disabled mother and I are comfortable. I’d choose this place again in a heartbeat!"
Kemi 2-night trip
Posted less than an hour ago
Motel 6 New Haven - Branford, CT

Find out more about Cheshire

Cheshire Cottages information

Number of reviews
104
Accommodation
74 Cottages
Lowest Price
CA $289
Highest Price
CA $796

Frequently asked questions

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What is there to do in Cheshire near my cottage?
If you want to fill up your itinerary in Cheshire, be sure to stop by Barker Character, Comic and Cartoon Museum. It's a favorite with tourists and locals alike.

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