Cheshire Vacation Rentals from CA $130: Short-Term Rentals for 2025

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Vacation Rentals in Cheshire

"Needed a place to sleep for a couple of nights and this worked for us."

CA $240 total

includes taxes & fees

Sep 1 - Sep 2

Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

"Loved the property and we will surely be coming back."

"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."

On the beach, sun loungers, beach towels

"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!"

"So comfy for the dog and I for a night. Just what we needed!"

CA $218 total

includes taxes & fees

Sep 9 - Sep 10

"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! "

"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"

CA $233 total

includes taxes & fees

Sep 14 - Sep 15

"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!"

"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. "

CA $224 total

includes taxes & fees

Aug 31 - Sep 1

"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. "

"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "

CA $615 total

includes taxes & fees

Sep 1 - Sep 2

CA $412 total

includes taxes & fees

Aug 31 - Sep 1

"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!"

"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"

CA $1,280 total

includes taxes & fees

Sep 3 - Sep 4

"We love being there do we extended our stay. Would have liked to stay even longer. Very relaxing and peaceful."

"Overall rating 5/5. I would recommend this home to other families and would stay again. "

Microwave, electric kettle, cookware/dishes/utensils, paper towels

"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."

CA $328 total

includes taxes & fees

Aug 31 - Sep 1

4 bedrooms, iron/ironing board, free WiFi, bed sheets

"Stunning cottage! Great location. Well-equipped kitchen! Comfy beds. Loved the views! Truly a special place!"

"Thank you so Much, the family had a great time. Found some good seaglass"

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Top Cheshire Hotel Reviews

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.

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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.

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Cheshire Vacation Rentals

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Vacation Rentals in Cheshire

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

Luxury Furnished Apartments by Hyatus Downtown at Yale

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

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

Cozy East Haven Home • Near Beach & Yale

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

Cozy apartment in charming Hartford with AC, WiFi

New!Quaint & Convenient Hideaway: Great Location

Totally Private Cozy studio in awesome Hartford with WiFi, AC

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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

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

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

Family Gem on Dyer Street

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Litchfield County Four Season Country Paradise

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Waterfront Cottage in Branford

Direct Waterfront Private Beach Escape

Top Cheshire Hotel Reviews

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