Holiday Rentals in Cheshire Historic District

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Our top choices for Cheshire Historic District holiday rentals

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (6 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is €225
includes taxes & fees
7 Apr - 8 Apr
Private Apartment in Berlin

Cozy Room in charming New Haven near Yale/Hospitals!

Cozy Room in charming New Haven near Yale/Hospitals!
The Hill
9.4 out of 10, Exceptional, (3 reviews)
"Very nice house and very clean I really love it "
United States
Peterson
The price is €137
includes taxes & fees
4 Apr - 5 Apr
Cozy Room in charming New Haven near Yale/Hospitals!

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)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is €223
includes taxes & fees
13 Apr - 14 Apr
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

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)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveller
The price is €227
includes taxes & fees
6 Apr - 7 Apr
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

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 €160
includes taxes & fees
9 Apr - 10 Apr
Spacious 2 Bedroom apartment close to Yale Bowl

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (23 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 €195
includes taxes & fees
13 Apr - 14 Apr
Family Stays: Middletown, CT

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 €251
includes taxes & fees
1 May - 2 May
Once the old Schools house now a newly furnished Apartment

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.
One bedroom in United States of America, New Haven

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is €282
includes taxes & fees
3 Apr - 4 Apr
Angelica’s safe haven @ west haven

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 €212
includes taxes & fees
7 Apr - 8 Apr
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

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 €251
includes taxes & fees
1 May - 2 May
All New 1BR with tons of Charm

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is €242
includes taxes & fees
3 Apr - 4 Apr
2BR Apartment Near Wesleyan 301

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 €195
includes taxes & fees
6 Apr - 7 Apr
Stocked home close to Yale, in Heart of New Haven

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)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is €273
includes taxes & fees
6 Apr - 7 Apr
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

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 €443
includes taxes & fees
13 Apr - 14 Apr
The Jewel of The Cove - Historic Coastal Retreat

Modern Studio Retreat

Modern Studio Retreat
Dwight
The price is €233
includes taxes & fees
8 Apr - 9 Apr
Modern Studio Retreat

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 €201
includes taxes & fees
6 Apr - 7 Apr
Bright Downtown Studio near Yale & East Rock!

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"This apartment was the perfect base for visiting family in Wallingford. It had everything we needed, was very clean, and super convenient to downtown cafes and restaurants. The train is a bit loud but to be expected! Will definitely stay again. "
United States
Kelsey S.
The price is €251
includes taxes & fees
1 May - 2 May
New Railside Residents

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is €406
includes taxes & fees
6 Apr - 7 Apr
Welcoming 4-bedroom house in charming Hamden

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
The price is €251
includes taxes & fees
3 May - 4 May
All new 1BR apartment with all the features you are looking for
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, apart-hotels, 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 €115 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?

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.