A stone tower with a metal gate, surrounded by trees and a stone wall.

Cheshire Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cheshire vacation rentals

A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is ￥19,145
￥32,653 total
includes taxes & fees
Sep 29 - Sep 30
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A spacious living area with a sofa, a dining table, and a kitchen in the background.

2. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is ￥43,482
￥87,788 total
includes taxes & fees
Oct 6 - Oct 7
#43- Modern Luxury Log Cabin Retreat - Fire Pit
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

3. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is ￥18,733
￥44,562 total
includes taxes & fees
Oct 5 - Oct 6
Newly Remodeled 1-BR Close to Everything yet Very Private
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

4. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is ￥18,559
￥44,148 total
includes taxes & fees
Oct 27 - Oct 28
Newly Remodeled with deck. Close to town center

5. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is ￥18,559
￥44,148 total
includes taxes & fees
Oct 19 - Oct 20
All New 1BR with tons of Charm
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

6. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is ￥18,559
￥44,148 total
includes taxes & fees
Oct 19 - Oct 20
Once the old Schools house now a newly furnished Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

7. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥18,559
￥44,148 total
includes taxes & fees
Oct 16 - Oct 17
All New Studio apartment in center of town
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

8. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is ￥18,559
￥44,148 total
includes taxes & fees
Oct 19 - Oct 20
All New Private and Cozy in great location
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

9. #23 COMFORT & LUXURY 3 BR/2 BA House

#23 COMFORT & LUXURY 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 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 ￥27,416
￥56,135 total
includes taxes & fees
Oct 7 - Oct 8
#23 COMFORT & LUXURY 3 BR/2 BA House
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

10. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is ￥18,559
￥44,148 total
includes taxes & fees
Oct 16 - Oct 17
All New Fully Furnished Cozy Studio
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

11. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is ￥23,592
￥59,216 total
includes taxes & fees
Oct 2 - Oct 3
1-bedroom vacation home 22 minutes from Quinnipiac University
A two-story house with a porch, a front door with a wreath, and a small garden area.

12. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is ￥18,402
￥49,630 total
includes taxes & fees
Oct 8 - Oct 9
Bear Retreat - 2-bedroom house in Waterbury
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

13. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is ￥42,466
￥95,194 total
includes taxes & fees
Sep 27 - Sep 28
The Cottage by the Woods -private getaway to relax
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

14. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is ￥34,750
￥71,872 total
includes taxes & fees
Oct 5 - Oct 6
#27- Luxury Collection
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

15. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥14,942
￥20,329 total
includes taxes & fees
Oct 26 - Oct 27
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

16. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is ￥10,954
￥38,692 total
includes taxes & fees
Oct 7 - Oct 8
The Sun Filled Cozy Creamery
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

17. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
8.8 out of 10, Excellent, (3 reviews)
"Convenient location & hosts"
United States
Northeast C.
The price is ￥15,431
￥39,058 total
includes taxes & fees
Sep 27 - Sep 28
Stylish Westville Apartment near Yale Campus
A modern kitchen with white cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

18. #26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
#26 Beautifully Renovated 2 BR Home
A deck with a white chair and a table, a sliding glass door, and a potted plant.

19. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is ￥27,524
￥49,353 total
includes taxes & fees
Sep 28 - Sep 29
Bristol Condo Near Espn HQ & Lake Compounce!
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

20. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is ￥17,780
￥33,068 total
includes taxes & fees
Sep 28 - Sep 29
Spacious 2 Bedroom apartment close to Yale Bowl
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

New Haven Hotel

New Haven Hotel

8/10 Good
"The staff members at check-in & check-out were warmly professional and attentive. What a gorgeous & spacious living room area with appealing decor. The breakfast options were fantastic for self-serve options. The room was immaculate. Two points that led me to rate it a 4.7 out of 5 = the extremely hard bed & non-working light & electric fixtures on the side of the bed by the window."
Maria Luisa 1-night trip
Posted 5 hours ago
New Haven Hotel

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!

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Cheshire Hollow Farm, 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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Cheshire vacation home rental. It is located on the beach and has a balcony, a barbecue grill, and air-conditioning 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 you can cook with friends or family.

What’s there to see and do in Cheshire?

Family-friendly attractions include Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, 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.