Cheshire Historic District Holiday Rentals

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Our top choices for Cheshire Historic District holiday rentals

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.
Once the old Schools house now a newly furnished Apartment
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is AU$361
includes taxes & fees
23 Mar - 24 Mar
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and very clean I really love it "
United States
Peterson
The price is AU$224
includes taxes & fees
17 Mar - 18 Mar
Cozy Room in charming New Haven near Yale/Hospitals!

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is AU$308
includes taxes & fees
17 Mar - 18 Mar
Cozy Guest Suite in Historic Home

Holiday Home in Middletown

Family Stays: Middletown, CT
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 AU$343
includes taxes & fees
13 Apr - 14 Apr
Family Stays: Middletown, CT

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$416
includes taxes & fees
8 Apr - 9 Apr
All New 1BR with tons of Charm
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 AU$259
includes taxes & fees
22 Mar - 23 Mar
Spacious 2 Bedroom apartment close to Yale Bowl
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is AU$456
includes taxes & fees
18 Mar - 19 Mar
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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 AU$744
includes taxes & fees
22 Mar - 23 Mar
The Jewel of The Cove - Historic Coastal Retreat
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 AU$503
includes taxes & fees
17 Mar - 18 Mar
Angelica’s safe haven @ west 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 AU$354
includes taxes & fees
17 Mar - 18 Mar
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
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 AU$356
includes taxes & fees
23 Mar - 24 Mar
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
The price is AU$219
includes taxes & fees
17 Mar - 18 Mar
One private bedroom with work space and shared home with spa.
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is AU$292
includes taxes & fees
22 Mar - 23 Mar
Stocked home close to Yale, in Heart of New Haven
8.6 out of 10, Excellent, (4 reviews)
"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 AU$270
includes taxes & fees
22 Mar - 23 Mar
One bedroom in United States of America, New Haven
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 AU$615
includes taxes & fees
18 Mar - 19 Mar
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
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 AU$302
includes taxes & fees
17 Mar - 18 Mar
Bright Downtown Studio near Yale & East Rock!

Holiday Home in West Haven

McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is AU$760
includes taxes & fees
17 Mar - 18 Mar
McAngel Haven: 5 mins from Yale
The price is AU$298
includes taxes & fees
17 Mar - 18 Mar
Cozy 2-bedroom apartment in charming New Haven near Downtown and Yale Hospital
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

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$182 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. 

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?

Oceanfront Getaway - Quiet, Firepit + Pvt Beach: This holiday home rental outside of Cheshire Historic District is located on the beach, and has a balcony, a garden and a BBQ 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 that 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 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.