Cheshire Historic District Vacation Rentals

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Check prices for these dates

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

Our top choices for Cheshire Historic District vacation rentals

Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining
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, (60)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale
4 bedrooms, iron/ironing board, free WiFi, bed sheets
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
Terrace/patio
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
Fridge, microwave, oven, stovetop
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.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop
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 ￥18,227
￥49,237 total
includes taxes & fees
Dec 14 - Dec 15
Private Apartment in Berlin
TV
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 ￥17,526
￥38,383 total
includes taxes & fees
Dec 14 - Dec 15
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
1 bedroom, desk, iron/ironing board, WiFi
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 ￥14,800
￥32,248 total
includes taxes & fees
Dec 11 - Dec 12
One bedroom apartment in United States of America, New Haven
Fridge, microwave, oven, stovetop
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 ￥21,421
￥47,848 total
includes taxes & fees
Dec 18 - Dec 19
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale

Stunning Apt W/ Parking and Gym | Downtown at Yale

The Hill
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale
1 bedroom, iron/ironing board, WiFi, bed sheets
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 ￥21,421
￥38,672 total
includes taxes & fees
Dec 11 - Dec 12
Downtown New Haven Escape
Seasonal outdoor pool
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
Dining
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
Beach nearby, beach towels
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.
Interior
Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements

Main Street Historic District
The price is ￥112,169
￥145,041 total
includes taxes & fees
Dec 11 - Dec 12
Conference Room Rental no sleeping arrangements
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

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 ￥14,021
￥19,240 total
includes taxes & fees
Dec 11 - Dec 12
New One Bedroom Apartment Centrally Located in Southbury
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

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 ￥14,956
￥33,028 total
includes taxes & fees
Dec 11 - Dec 12
Charming Studio| Near Yale| Downtown New Haven
1 bedroom, WiFi, bed sheets
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 ￥12,463
￥20,136 total
includes taxes & fees
Dec 16 - Dec 17
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Fridge, microwave, oven, stovetop
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
Smart TV, fireplace, video games
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 ￥91,137
￥148,039 total
includes taxes & fees
Dec 14 - Dec 15
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Shared Dormitory, 1 Bedroom | Outdoor dining
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
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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Everything was great 👍 "
Janet 3-night trip
Posted 1 day ago
Courtyard by Marriott Waterbury Downtown

Find out more about Cheshire Historic District

Search for holiday rentals in Cheshire Historic District on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire Historic District using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cheshire Historic District!

Frequently asked questions

Can I find vacation rentals in Cheshire Historic District?

Yes, there are vacation rentals near popular sights in Cheshire Historic District, or you can go with a 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 vacation home rentals in Cheshire Historic District?

Private Apartment in Berlin: This vacation 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 larger area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are vacation rentals like in Cheshire Historic District?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Cheshire Historic District. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.