Cheshire Historic District Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Cheshire Historic District vacation rentals

TV

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥21,961
￥48,330 total
includes taxes & fees
Apr 17 - Apr 18
Once the old Schools house now a newly furnished Apartment
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, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is ￥19,893
￥40,104 total
includes taxes & fees
Mar 24 - Mar 25
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Private kitchen

Cozy Room in charming New Haven near Yale/Hospitals!

Cozy Room in charming New Haven near Yale/Hospitals!
The Hill
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and very clean I really love it "
United States
Peterson
The price is ￥11,458
￥24,595 total
includes taxes & fees
Mar 18 - Mar 19
Cozy Room in charming New Haven near Yale/Hospitals!
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is ￥23,489
￥34,174 total
includes taxes & fees
Mar 23 - Mar 24
Cozy Guest Suite in Historic Home
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (22 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is ￥19,893
￥37,836 total
includes taxes & fees
Apr 13 - Apr 14
Family Stays: Middletown, CT
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥18,301
￥44,121 total
includes taxes & fees
Apr 8 - Apr 9
All New 1BR with tons of Charm
Dining

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, (70 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is ￥14,004
￥28,438 total
includes taxes & fees
Mar 22 - Mar 23
Spacious 2 Bedroom apartment close to Yale Bowl
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"Clean, quiet, as advertised. "
United States
Anonymous traveler
The price is ￥24,205
￥46,933 total
includes taxes & fees
Mar 18 - Mar 19
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Terrace/patio

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
9.8 out of 10, Exceptional, (7 reviews)
"This was a great place to stay in New Haven, and a lot of care has gone into making it a welcoming house."
United States
Geoffrey H.
The price is ￥32,942
￥82,442 total
includes taxes & fees
Mar 24 - Mar 25
The Jewel of The Cove - Historic Coastal Retreat
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"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 ￥23,075
￥54,983 total
includes taxes & fees
Mar 20 - Mar 21
Angelica’s safe haven @ west haven
Marina

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is ￥20,370
￥37,748 total
includes taxes & fees
Mar 30 - Mar 31
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (14 reviews)
"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 ￥12,254
￥38,905 total
includes taxes & fees
Mar 23 - Mar 24
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Microwave, oven, stovetop, dishwasher

One private bedroom with work space and shared home with spa.

One private bedroom with work space and shared home with spa.
Rocky Hill
The price is ￥16,471
￥23,955 total
includes taxes & fees
Mar 18 - Mar 19
One private bedroom with work space and shared home with spa.
Dining

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is ￥17,187
￥31,915 total
includes taxes & fees
Mar 22 - Mar 23
Stocked home close to Yale, in Heart of New Haven
Fridge, microwave, oven, stovetop

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
8.6 out of 10, Excellent, (4 reviews)
"Good location "
United States
Christopher S.
The price is ￥12,731
￥29,719 total
includes taxes & fees
Mar 23 - Mar 24
One bedroom in United States of America, New Haven
Exterior

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is ￥28,751
￥68,085 total
includes taxes & fees
Mar 18 - Mar 19
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (13 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is ￥15,556
￥36,079 total
includes taxes & fees
Mar 19 - Mar 20
Bright Downtown Studio near Yale & East Rock!
Dining

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is ￥36,523
￥83,697 total
includes taxes & fees
Mar 22 - Mar 23
McAngel Haven: 5 mins from Yale
WiFi, bed sheets

Cozy 2-bedroom apartment in charming New Haven near Downtown and Yale Hospital

Cozy 2-bedroom apartment in charming New Haven near Downtown and Yale Hospital
The Hill
The price is ￥25,462
￥32,464 total
includes taxes & fees
Mar 18 - Mar 19
Cozy 2-bedroom apartment in charming New Haven near Downtown and Yale Hospital
Desk, iron/ironing board, WiFi, bed sheets

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
1 Min to I-91 - Newly Renovated Modern 2 BR Home
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Ok"
reggie 1-night trip
Posted 10 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Cheshire Historic District

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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?

Oceanfront Getaway - Quiet, Firepit + Pvt Beach: This vacation home rental outside of Cheshire Historic District is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.