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Cheshire Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Holiday Rentals in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop

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 HK$738
HK$1,365 total
includes taxes & fees
29 Aug - 30 Aug
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Luxury Furnished Apartments by Hyatus Downtown at Yale
In-room dining

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

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
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (124)
"We had a magical stay in this truly enchanting home the beds were comfortable. The kitchen well equipt for entertaining a large crowd. The fire place and piano were the backdrop for many intimate moments. The gardens were beautiful with azaleas and many perennials. The location directly across from the beach allowed for many walks and playtime together and the waves sung us to sleep at night. We would love to make a new family tradition for visiting here again and again."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Cozy Home Near New Haven
Microwave, oven, stovetop, dishwasher

Cozy Home Near New Haven

10.0 out of 10, Exceptional, (1)
"So comfy for the dog and I for a night. Just what we needed!"
The price is HK$938
HK$1,235 total
includes taxes & fees
9 Sept - 10 Sept
Cozy Home Near New Haven
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (139)
"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
Cozy apartment in charming Hartford with AC, WiFi
Microwave

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 HK$898
HK$1,324 total
includes taxes & fees
14 Sept - 15 Sept
Cozy apartment in charming Hartford with AC, WiFi
New!Quaint & Convenient Hideaway: Great Location
Fridge, microwave, oven, stovetop

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
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Living area

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (1)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Totally Private Cozy studio in awesome Hartford with WiFi, AC
WiFi, bed sheets

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 HK$852
HK$1,271 total
includes taxes & fees
31 Aug - 1 Sept
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Dining

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
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (59)
"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. "
The price is HK$2,032
HK$3,550 total
includes taxes & fees
28 Aug - 29 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

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
Terrace/patio

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
Family Gem on Dyer Street
Dining

Family Gem on Dyer Street

The price is HK$3,285
HK$7,279 total
includes taxes & fees
3 Sept - 4 Sept
Family Gem on Dyer Street
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

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

9.0 out of 10, Wonderful, (22)
"We love being there do we extended our stay. Would have liked to stay even longer. Very relaxing and peaceful."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Litchfield County Four Season Country Paradise
Outdoor pool, a heated pool

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (48)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Microwave, electric kettle, cookware/dishes/utensils, paper towels

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

10.0 out of 10, Exceptional, (3)
"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."
The price is HK$1,055
HK$1,874 total
includes taxes & fees
27 Aug - 28 Aug
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Waterfront Cottage in Branford
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (95)
"Stunning cottage! Great location. Well-equipped kitchen! Comfy beds. Loved the views! Truly a special place!"
Waterfront Cottage in Branford
Direct Waterfront Private Beach Escape
Outdoor dining

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (17)
"Thank you so Much, the family had a great time. Found some good seaglass"
Direct Waterfront Private Beach Escape
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Booking my next stay now!"
Christina 2-night trip
Posted 2 days ago
Cambria Hotel New Haven University Area

Find out more about Cheshire

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:

  • View our selection of featured holiday rentals in Cheshire
  • Use the map to find apartments and other holiday homes in the Cheshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheshire while they last

Look no further and take a look at our great range of rental properties in Cheshire!

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Frequently asked questions

Can I find a holiday rental in Cheshire?

Yes, there are holiday rentals in Cheshire close to Barker Character, Comic and Cartoon Museum, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Cheshire has to offer?

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views: This holiday home rental outside of Cheshire is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 holiday rental in Cheshire like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cheshire. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.