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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

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

Waterfront Cottage in Branford
Exterior

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (90)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford
Historic Whitneyville Cottage
Exterior detail

Historic Whitneyville Cottage

9.6 out of 10, Exceptional, (14)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville 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, (29)
"Vladimir and Cristina's Plymouth listing is such a great find! It was a great home base for visiting family in the area for the holidays. I don't think I've ever been to a rental that had everything you could possibly need. All this plus an amazing view - we'll be back!"
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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
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
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
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!
Direct waterfront cottage on private sandy beach
Beach

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (2)
"Enjoyed our stay very much. Cute cottage, rustic. Only downside was the airport is close "
Direct waterfront cottage on private sandy beach
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, (9)
"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!
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
Charming 3 Bedroom Beach Front Cottage
Living room with view of ocean

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (2)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
Charming 3 Bedroom Beach Front Cottage
Charming Branford Cottage Steps to Beach, Cozy Retreat with Grill, Fire Pit, Beach Gear, and More!
Beachside Bliss: Just steps away from the sand

Charming Branford Cottage Steps to Beach, Cozy Retreat with Grill, Fire Pit, Beach Gear, and More!

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Charming Branford Cottage Steps to Beach, Cozy Retreat with Grill, Fire Pit, Beach Gear, and More!
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!
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
Family Friendly Cottage for 8 with Arcade Games!!
Eat in Kitchen

Family Friendly Cottage for 8 with Arcade Games!!

10.0 out of 10, Exceptional, (4)
"We had a wonderful family Thanksgiving gathering. The space is very open and welcoming. The basement games are a fun addition. The beds were comfortable and the linens of good quality. Nancy was very quick and supportive with any questions we had. Although it's close to the Tweed New Haven airport, we were not bothered by the planes and at night they don't seem to fly. "
Family Friendly Cottage for 8 with Arcade Games!!
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!

9.0 out of 10, Wonderful, (4)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
Modern Terryville Cottage w/ Deck & Lake View!
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
Guilford Carriage House at Granite Lodge!
Living area

Guilford Carriage House at Granite Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
Available July 1, 2024 2 week or monthly July /August
The Enchanted Cottage

Available July 1, 2024 2 week or monthly July /August

Available July 1, 2024 2 week or monthly July /August
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, (2002)
"The room layout, amenities and cleanliness were excellent. Think about adding a continental breakfast."
The price is AED 324
AED 373 total
includes taxes & fees
16 Feb - 17 Feb
New Haven Village Suites
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, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Exterior image

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
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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