Cheshire Vacation Rentals from ￥13,917: Search Short-Term Rentals

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Vacation Rentals in Cheshire

Our top choices for Cheshire vacation rentals

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

￥25,725 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!"

￥23,371 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"

￥24,962 total

includes taxes & fees

Sep 7 - Sep 8

"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. "

￥23,946 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. "

￥66,915 total

includes taxes & fees

Aug 31 - Sep 1

￥44,468 total

includes taxes & fees

Aug 29 - Aug 30

"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"

￥137,160 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."

￥35,308 total

includes taxes & fees

Aug 29 - Aug 30

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

Search for holiday rentals in Cheshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire using one of the methods below:

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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

Our top choices for Cheshire vacation rentals

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 Home Near New Haven

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

Find out more about Cheshire

Frequently asked questions