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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Cheshire apartments

Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is AED 547
AED 886 total
includes taxes & fees
21 Jul - 22 Jul
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV, fireplace, books, music library

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (33 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is AED 544
AED 1,019 total
includes taxes & fees
15 Jul - 16 Jul
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Interior

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is AED 2,645
AED 3,420 total
includes taxes & fees
4 Jul - 5 Jul
Conference Room Rental no sleeping arrangements
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is AED 446
AED 1,134 total
includes taxes & fees
5 Jul - 6 Jul
2BR Apartment Near Wesleyan 301
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.0 out of 10, Very Good, (1 review)
"Excellent beds and clean."
United States
DANIEL M.
The price is AED 617
AED 1,256 total
includes taxes & fees
6 Jul - 7 Jul
2BR Apartment Near Wesleyan 102
Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
The price is AED 716
AED 1,474 total
includes taxes & fees
29 Jul - 30 Jul
3 BR Apartment Near Wesleyan 201
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is AED 500
AED 1,210 total
includes taxes & fees
7 Jul - 8 Jul
Private Apt in Middletown-Wesleyan 101
3 bedrooms, free WiFi

Location, is the key for this 3 bedroom!

Location, is the key for this 3 bedroom!
Frog Hollow
9.4 out of 10, Exceptional, (6 reviews)
"It was nice and close to where we had a wedding. Plenty of room for us all. Host was very easy to contact. "
United States
Shawn R.
The price is AED 681
AED 1,681 total
includes taxes & fees
7 Jul - 8 Jul
Location, is the key for this 3 bedroom!
Dining

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New Britain
7.6 out of 10, Good, (7 reviews)
" Not bad for the price "
United States
Audrey L.
The price is AED 506
AED 1,366 total
includes taxes & fees
11 Jul - 12 Jul
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Terrace/patio

The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (18 reviews)
"Great location and pleasant area to walk to area restaurants and shops. Prompt and friendly communication with host who was very accommodating to our needs. We enjoyed our stay."
United States
Laurie R.
The Blue Back Bungalow
Terrace/patio

West Hartford Center: Cozy New England Apartment

West Hartford Center: Cozy New England Apartment
West Hartford
10.0 out of 10, Exceptional, (11 reviews)
"Great comfortable spot- great location!"
United States
Sara H.
The price is AED 869
AED 1,679 total
includes taxes & fees
5 Jul - 6 Jul
West Hartford Center: Cozy New England Apartment
Interior

West Hartford Center: Charming New England Apt

West Hartford Center: Charming New England Apt
West Hartford
10.0 out of 10, Exceptional, (7 reviews)
"Immaculate, nice decor, very comfortable beds, every detail is well thought out. "
United States
Cathryna B.
West Hartford Center: Charming New England Apt
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AED 433
AED 1,071 total
includes taxes & fees
5 Jul - 6 Jul
All New 1BR with tons of Charm
Interior

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
The price is AED 433
AED 1,071 total
includes taxes & fees
21 Jul - 22 Jul
New Railside Residents
TV

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 AED 433
AED 1,071 total
includes taxes & fees
10 Jul - 11 Jul
All New Private and Cozy in great location
Fridge, microwave, oven, stovetop

Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is AED 433
AED 1,071 total
includes taxes & fees
22 Jul - 23 Jul
Fully Furnished 1BR Apartment
TV

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 AED 433
AED 1,060 total
includes taxes & fees
28 Jul - 29 Jul
Newly Remodeled with deck. Close to town center
TV

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is AED 433
AED 1,071 total
includes taxes & fees
6 Jul - 7 Jul
All new 1BR apartment with all the features you are looking for
Interior

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
East Shore
10.0 out of 10, Exceptional, (2 reviews)
"Had a Great stay at the nauti nook!"
United States
David D.
The price is AED 584
AED 1,799 total
includes taxes & fees
6 Jul - 7 Jul
Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
TV

Relaxing 3-bedroom apartment in New Haven

Relaxing 3-bedroom apartment in New Haven
New Haven
8.0 out of 10, Very Good, (1 review)
"To be honest with you overall the stay was decent. The host was very accommodating for us as we wanted to check in early due to our flight, arriving in the morning. When we had issues with the linens needing to be changed I called our host she was super responsive and immediately had housekeeping there to rectify our issues. The only thing I could say about the property is the furniture, especially in the living area needs to be updated. Also, the property could use some TLC when it comes to the...
United States
S F.
The price is AED 661
AED 1,425 total
includes taxes & fees
6 Jul - 7 Jul
Relaxing 3-bedroom apartment in New Haven
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

Hilton Garden Inn Milford

Hilton Garden Inn Milford

10/10 Excellent
"Easy access from highway.. excellent staff. Very good food. 10 out of 10"
Adrian 1-night trip
Posted less than an hour ago
Hilton Garden Inn Milford

Frequently asked questions

What's it like to stay at an apartment in Cheshire?
There might not be many choices centrally in Cheshire, but Expedia can help you locate accommodations within the larger area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as vacation homes, condos, or guest houses. Any visit to a new destination can be a culinary trip so why not visit the local restaurants?
Why choose an apartment over a traditional hotel room?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and is often more spacious than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, and also for families who want the conveniences of home.
What's the best apartment I should consider for a stay in Cheshire?
Below are some of the more popular apartments in the area: Landing in Downtown Hartford Near Dunkin' Park: Located in Hartford, 21.9 mi/35.3 km from the heart of Cheshire. Includes laundry facilities and Smart TVs. Free parking and a fitness center are on site. Landing Apartments New Haven Near Dixwell: Located 12.9 mi/20.7 km away in New Haven. Stocked home close to Yale, in Heart of New Haven: Located in New Haven, 13.7 mi/22.1 km away. Includes free WiFi, sofa beds, and Smart TVs. Access to onsite laundry facilities is available on site. Luxurious 3BR Apartment with Premium Amenities: Located 14.3 mi/23.1 km away in New Haven. Free WiFi, private balconies, and separate dining areas are included. Onsite laundry facilities and a game room are on site. 1ST FLR APT Your Private Resort, now FAMILY-ized: 1 BR + LR suitable for 2 kids: Located in Shelton, 19.4 mi/31.2 km from Cheshire. Includes a private pool, free WiFi, and private patios. Access to an outdoor pool is available on site.
What will the weather be like when I travel to Cheshire?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Cheshire. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Cheshire is 54 inches.
What should I see in Cheshire?
Cheshire is known for its restaurants. Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, whereas Roaring Brook Park and Drazen Orchards are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Bartlem Park are other places worth a visit.
What's the best way to get to and around Cheshire?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Oxford, CT (OXC-Waterbury - Oxford), which is located 12 mi (19.3 km) from the heart of the city. Otherwise, look for flights into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.5 mi (26.6 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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