Cheshire Historic District Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Cheshire Historic District holiday rentals

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
The Hill
9.6 out of 10, Exceptional, (61)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
New Britain
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 NZ$423
includes taxes & fees
16 Dec - 17 Dec
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont
4.0 star property
The Hill
9.4 out of 10, Exceptional, (22)
"Easily accessible, very clean and pleasant place to stay."
Canada
Kirsten
Luxury Apartments by Hyatus at Pierpont

Waterfront Cottage in Branford

Waterfront Cottage in Branford
branford
10.0 out of 10, Exceptional, (98)
"Beautiful location "
United States
Anne d.
Waterfront Cottage in Branford

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
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 NZ$544
includes taxes & fees
16 Dec - 17 Dec
Private Apartment in Berlin

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is NZ$353
includes taxes & fees
18 Dec - 19 Dec
One bedroom apartment in United States of America, New Haven

Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach
Branford
10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation!! The house was perfect, check in couldn’t have easier and the views couldn’t have been better. A perfect summer getaway."
United States
Mike S.
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
West New Haven
9.4 out of 10, Exceptional, (3)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is NZ$223
includes taxes & fees
17 Dec - 18 Dec
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
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 NZ$281
includes taxes & fees
16 Dec - 17 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is NZ$1,603
includes taxes & fees
16 Dec - 17 Dec
Conference Room Rental no sleeping arrangements

Gorgeous 4BR Beach House with Private Beach Access.

Gorgeous 4BR Beach House with Private Beach Access.
Pine Orchard
9.8 out of 10, Exceptional, (76)
"Nice property, thanks to the owners.Jackie"
United States
Jacqueline M.
Gorgeous 4BR Beach House with Private Beach Access.

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
Washington Street Historic District
6.6 out of 10, (4)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
United States
Jenn U.
The price is NZ$332
includes taxes & fees
22 Dec - 23 Dec
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
8.8 out of 10, Excellent, (11)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is NZ$289
includes taxes & fees
16 Dec - 17 Dec
Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven Escape

Downtown New Haven Escape
2.0 star property
Dwight
8.0 out of 10, Very good, (6)
"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 NZ$417
includes taxes & fees
8 Jan - 9 Jan 2026
Downtown New Haven Escape

New Cozy 2BR Stay New Haven Close to Yale

New Cozy 2BR Stay New Haven Close to Yale
2.0 star property
East Rock
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
United States
CHUCK C.
New Cozy 2BR Stay New Haven Close to Yale

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
2.0 star property
West Hartford
8.6 out of 10, Excellent, (9)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is NZ$529
includes taxes & fees
18 Dec - 19 Dec
Charming 3-Bedroom Home with Modern Comforts in West Hartford

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (24)
"As advertised. Enjoyed our stay. "
United States
Jeff C.
The price is NZ$1,636
includes taxes & fees
16 Dec - 17 Dec
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Room-plaid Room 3min From Yale Univ

Room-plaid Room 3min From Yale Univ
3.0 star property
Newhallville
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
United States
Colby
Room-plaid Room 3min From Yale Univ

Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth
9.8 out of 10, Exceptional, (40)
"Our stay was so peaceful and relaxing. The property was beautiful and exactly as described in the listing. We loved having a fire outside, sitting in the screened-in porch. Will absolutely be coming back!"
United States
Jean R.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy dog friendly updated house in quiet village adjacent to park

Cozy dog friendly updated house in quiet village adjacent to park
Northford
10.0 out of 10, Exceptional, (44)
"Perfect!We travel with our large family, several times a year, this is by far the house with the most, everything!Family friendly layout/amenities. The place is beautiful, we will definitely plan to return for a longer stay!And the host is amazing!"
United States
Christina v.
Cozy dog friendly updated house in quiet village adjacent to park
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Historic District Hotel Reviews

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 favorite 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 depends 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 NZ$223 per night. Entering your travel dates in the search wizard you might find 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. 

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.