Cheshire Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Cheshire holiday rentals

Smart TV

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (16 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
The price is HK$915
HK$1,569 total
includes taxes & fees
22 Mar - 23 Mar
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV, fireplace, books, music library

Apartment in Haddam

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is HK$978
HK$1,979 total
includes taxes & fees
10 Mar - 11 Mar
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Smart TV

Apartment in Southington

#23 *COMFORT & LUXURY* 3 BR/2 BA House
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is HK$1,188
HK$2,712 total
includes taxes & fees
9 Mar - 10 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
TV

Holiday Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$989
HK$2,366 total
includes taxes & fees
4 Mar - 5 Mar
Once the old Schools house now a newly furnished Apartment
Cookware/dishes/utensils

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.8 out of 10, Exceptional, (14 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is HK$1,298
HK$2,700 total
includes taxes & fees
14 Mar - 15 Mar
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$989
HK$2,366 total
includes taxes & fees
4 Mar - 5 Mar
All New 1BR with tons of Charm
Exterior

Apartment in West Haven

Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is HK$1,021
HK$2,572 total
includes taxes & fees
4 Mar - 5 Mar
Angelica’s safe haven @ west haven
1 bedroom, desk, iron/ironing board, WiFi

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
The price is HK$743
HK$1,596 total
includes taxes & fees
15 Mar - 16 Mar
One bedroom apartment in United States of America, New Haven
Marina

Holiday Home in Fair Haven

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is HK$1,322
HK$2,482 total
includes taxes & fees
9 Mar - 10 Mar
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Terrace/patio

Holiday Home in East Shore

The Jewel of The Cove - Historic Coastal Retreat
9.8 out of 10, Exceptional, (7 reviews)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
The price is HK$1,619
HK$4,036 total
includes taxes & fees
10 Mar - 11 Mar
The Jewel of The Cove - Historic Coastal Retreat
Marina

Holiday Home in Fair Haven

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is HK$901
HK$1,787 total
includes taxes & fees
4 Mar - 5 Mar
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Interior

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is HK$1,154
HK$1,680 total
includes taxes & fees
8 Mar - 9 Mar
Cozy Guest Suite in Historic Home
Private kitchen

Holiday Home in The Hill

Cozy Room in charming New Haven near Yale/Hospitals!
10.0 out of 10, Exceptional, (1 review)
"Super great communication and help getting situated in the room!"
United States
Glenn
The price is HK$563
HK$1,209 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Room in charming New Haven near Yale/Hospitals!
1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Dwight

Downtown New Haven Escape
8.0 out of 10, Very good, (6 reviews)
"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."
United States
Michael H.
The price is HK$1,024
HK$1,887 total
includes taxes & fees
5 Mar - 6 Mar
Downtown New Haven Escape
Interior

Apartment in West New Haven

The Nest At Elm City Flats.
9.6 out of 10, Exceptional, (9 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
The price is HK$697
HK$1,812 total
includes taxes & fees
15 Mar - 16 Mar
The Nest At Elm City Flats.

Condo in Downtown New Haven

Bright Downtown Studio near Yale & East Rock!
9.0 out of 10, Wonderful, (13 reviews)
"Everything was great and just as charming as the photo indicated. "
United States
Nancy F.
The price is HK$867
HK$2,044 total
includes taxes & fees
4 Mar - 5 Mar
Bright Downtown Studio near Yale & East Rock!

Apartment in East Rock

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
10.0 out of 10, Exceptional, (4 reviews)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is HK$1,486
HK$3,471 total
includes taxes & fees
4 Mar - 5 Mar
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
Interior

Apartment in Milford

Beach Apartment in Woodmont Milford
9.0 out of 10, Wonderful, (2 reviews)
"Had a great stay!"
United States
Garry G.
The price is HK$676
HK$2,369 total
includes taxes & fees
4 Mar - 5 Mar
Beach Apartment in Woodmont Milford
TV

Apartment in Dwight

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
8.0 out of 10, Very good, (2 reviews)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is HK$1,075
HK$1,824 total
includes taxes & fees
4 Mar - 5 Mar
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Exterior

Apartment in Downtown Hartford

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
9.4 out of 10, Exceptional, (6 reviews)
"Great location. Clean property"
United States
Sue R.
The price is HK$899
HK$1,783 total
includes taxes & fees
4 Mar - 5 Mar
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
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

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Clean , quiet and friendly staff !! Excellent stay "
Theresa 2-night trip
Posted 2 hours ago
Hampton Inn & Suites Hartford/Farmington

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
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  • 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!

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?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: This holiday home rental outside of Cheshire is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 balcony, a garden and a selection of books 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 Roaring Brook Park and Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Drazen Orchards 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.