Cheshire Historic District Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Cheshire Historic District holiday rentals

Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.6 out of 10, Exceptional, (10)
"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 AU$382
includes taxes & fees
17 Dec - 18 Dec
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior
Family Stays: Middletown, CT

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (18)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is AU$328
includes taxes & fees
15 Dec - 16 Dec
Family Stays: Middletown, CT
Property grounds
#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home in Middletown

#24 *Serenity* A Lakefront Cottage Retreat
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is AU$443
includes taxes & fees
14 Dec - 15 Dec
#24 *Serenity* A Lakefront Cottage Retreat
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is AU$422
includes taxes & fees
14 Dec - 15 Dec
Soothing 2-bedroom lower-level apartment in Berlin
Interior
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (2)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is AU$359
includes taxes & fees
8 Jan - 9 Jan 2026
Westville Stay • 2BR • Near Yale • Free Parking
Exterior
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Apartment in East Rock

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is AU$569
includes taxes & fees
14 Dec - 15 Dec
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Exterior
Angelica’s safe haven @ west haven

Apartment in West Haven

Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (6)
"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 AU$508
includes taxes & fees
12 Dec - 13 Dec
Angelica’s safe haven @ west haven
Smart TV, fireplace, books, music library
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Apartment in Haddam

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (27)
"Overall wonderful experience, would highly recommend."
United States
Steven R.
The price is AU$388
includes taxes & fees
18 Dec - 19 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Bar (on property)
Modern Studio Stay On Howe

Apartment in Dwight

Modern Studio Stay On Howe
2.0 star property
9.0 out of 10, Wonderful, (4)
"Cute, clean property good for a visit to New Haven for a single or couple. The area is a little noisy, but that's the price you pay for being in close walking distance to everything you'd want to be in close walking distance to! Would definitely stay again. "
United States
Robin A.
The price is AU$440
includes taxes & fees
15 Dec - 16 Dec
Modern Studio Stay On Howe
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is AU$248
includes taxes & fees
15 Dec - 16 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Interior
Charming New England Tiny Home in Cromwell, CT

Apartment in Main Street Historic District

Charming New England Tiny Home in Cromwell, CT
10.0 out of 10, Exceptional, (1)
"It was the perfect escape- close enough to home but just far enough to feel like a vacation, the whole process was 10 out of 10 and def worth a 2nd stay!"
United States
Amanda G.
The price is AU$326
includes taxes & fees
18 Dec - 19 Dec
Charming New England Tiny Home in Cromwell, CT
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is AU$365
includes taxes & fees
14 Dec - 15 Dec
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
8.8 out of 10, Excellent, (11)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is AU$267
includes taxes & fees
17 Dec - 18 Dec
Charming Studio| Near Yale| Downtown New Haven
Interior
Private Apartment in Berlin

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is AU$478
includes taxes & fees
14 Dec - 15 Dec
Private Apartment in Berlin
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Holiday Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (1)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is AU$729
includes taxes & fees
18 Dec - 19 Dec
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Dining
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Apartment in New Britain

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
7.6 out of 10, Good, (7)
" Not bad for the price "
United States
Audrey L.
The price is AU$563
includes taxes & fees
12 Dec - 13 Dec
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Fridge, microwave, oven, stovetop
All New Fully Furnished Cozy Studio

Apartment in Wallingford Center

All New Fully Furnished Cozy Studio
9.8 out of 10, Exceptional, (8)
"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 AU$437
includes taxes & fees
14 Dec - 15 Dec
All New Fully Furnished Cozy Studio
3 bedrooms, iron/ironing board, WiFi, bed sheets
Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr

Apartment in East Rock

Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr
9.0 out of 10, Wonderful, (10)
"Great 4 day visit to New Haven. We enjoyed the neighborhood and proximity to Yale."
United States
Todd L.
The price is AU$477
includes taxes & fees
14 Dec - 15 Dec
Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr
Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$188
includes taxes & fees
14 Dec - 15 Dec
New One Bedroom Apartment Centrally Located in Southbury
Microwave, oven, stovetop, dishwasher
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Apartment in West New Haven

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
9.4 out of 10, Exceptional, (3)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is AU$197
includes taxes & fees
11 Jan - 12 Jan 2026
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
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 Historic District Hotel Reviews

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

10/10 Excellent
"Clean, spacious and the staff is great! Second time there in the last 6 months and will continue to stay there every time I go to CT. "
Frances 3-night trip
Posted 2 days ago
Home2 Suites by Hilton East Haven New Haven

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire Historic District holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire Historic District holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cheshire Historic District holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire Historic District. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire Historic District holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire Historic District holiday rentals we have selected for you start as low as AU$188 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cheshire Historic District rentals

At Expedia, we put the best Cheshire Historic District holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cheshire Historic District rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire Historic District holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire Historic District. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Cheshire Historic District?

Yes, there are holiday rentals close to the most popular sights in Cheshire Historic District, or you can select a more secluded option if you're looking for a relaxing stay. Cheshire Historic District is known for its churches and university setting.

What are some of the best holiday rentals that Cheshire Historic District has to offer?

Private Apartment in Berlin: This holiday home rental outside of Cheshire Historic District is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Cheshire Historic District?

Explore the area and family-friendly sights such as Lake Compounce, or get out into nature at a spot like Mount Carmel. In the wider area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are holiday rentals like in Cheshire Historic District?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire Historic District. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.