Photo by Tai Bui

Cheshire Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

9.6 out of 10, Exceptional, (7)
"Needed a place to sleep for a couple of nights and this worked for us."
The price is CA $130
CA $240 total
includes taxes & fees
Sep 1 - Sep 2
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (54)
"Loved the property and we will surely be coming back."
Luxury Furnished Apartments by Hyatus Downtown at Yale

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

10.0 out of 10, Exceptional, (141)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (1)
"The check in process was very easy. The home was airy and bright. My family and I felt the peace and relaxation of the home. The kitchen was large and clean."
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (124)
"The house is beautiful, and one of the most unique and homey places we have everything stayed. Very spacious with lots of artwork, and arts and crafts style woodwork. The view of the sound is so serene. We enjoyed very much sitting out on the porch and gazing at the water and the passerbys, and taking walks along the sound. It has everything you need and then some. Thank you so much for sharing your gracious and beautiful home with us!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (66)
"Delightful to be on the water, spacious house for a family, responsive owner, a worthwhile trip! "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Charming Studio| Near Yale| Downtown New Haven

10.0 out of 10, Exceptional, (3)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is CA $159
CA $308 total
includes taxes & fees
Sep 3 - Sep 4
Charming Studio| Near Yale| Downtown New Haven

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.2 out of 10, Wonderful, (9)
"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "
The price is CA $199
CA $284 total
includes taxes & fees
Sep 1 - Sep 2
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

The price is CA $210
CA $415 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (3)
"All was as advertised. The Xfinity INDOOR theatre us across the the street. Xfinity OUTDOOR theatre/ arena is only about a .8 mile walk away. We took an UBER there and walked back after our concert"
The price is CA $158
CA $233 total
includes taxes & fees
Sep 7 - Sep 8
Cozy apartment in charming Hartford with AC, WiFi

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is CA $315
CA $717 total
includes taxes & fees
Sep 2 - Sep 3
McAngel Haven: 5 mins from Yale

New!Quaint & Convenient Hideaway: Great Location

9.8 out of 10, Exceptional, (12)
"Our family of 4 stayed there while visiting Hartford for our daughter’s college graduation. Great location great property and responsive host. Would def stay again!"
New!Quaint & Convenient Hideaway: Great Location

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.8 out of 10, Exceptional, (11)
"Beautiful area, close to the beach, with a wonderfully kept house."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (6)
"Enjoyed our stay very much. Cute cottage, rustic. Only downside was the airport is close "
Direct waterfront cottage on private sandy beach

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (8)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

10.0 out of 10, Exceptional, (1)
"This place was very clean and Michael was great, answering all my questions quickly. check in was simple just a code to get in it was very updated and the beds were very comfortable. It was close to Yale and to some great pizza places"
Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

Angelica’s safe haven @ west haven

10.0 out of 10, Exceptional, (4)
"This place was perfect for our weekend trip to New Haven. Angelica was a great Host, and communicated timely and clear. I would stay again if I ever come back to New Haven. "
The price is CA $188
CA $465 total
includes taxes & fees
Sep 2 - Sep 3
Angelica’s safe haven @ west haven

Blue Back Bungalow

2.0 star property
9.4 out of 10, Exceptional, (14)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is CA $152
CA $510 total
includes taxes & fees
Sep 3 - Sep 4
Blue Back Bungalow

Family Gem on Dyer Street

The price is CA $578
CA $1,280 total
includes taxes & fees
Sep 3 - Sep 4
Family Gem on Dyer Street
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Hotel Reviews

Find out more about Cheshire

Find out more about Cheshire

Everything you need to know about Cheshire vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cheshire vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire vacation rentals we have selected for you start as low as CA $130 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cheshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Barker Character, Comic and Cartoon Museum, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best vacation home rentals in Cheshire?

Modern Beach Home - Waterview, close to restaurants, universities and hospitals: Visitors like this Cheshire vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Cheshire?

Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, whereas Drazen Orchards and Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Roaring Brook Park are other places worth a visit.

What’s a vacation rental in Cheshire like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Cheshire. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.