Holiday Rentals in Cheshire Historic District

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Our top choices for Cheshire Historic District holiday rentals

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
#2 *Beautiful 1 BR Apartment - Central CT*

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
#24 *Serenity* A Lakefront Cottage Retreat

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 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 €190
includes taxes & fees
24 Feb - 25 Feb
Family Stays: Middletown, CT

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, (11 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 €230
includes taxes & fees
12 Feb - 13 Feb
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.2 out of 10, Wonderful, (5 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.
Private Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is €266
includes taxes & fees
16 Feb - 17 Feb
Soothing 2-bedroom lower-level apartment in Berlin

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 €218
includes taxes & fees
17 Feb - 18 Feb
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

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 €294
includes taxes & fees
23 Feb - 24 Feb
Angelica’s safe haven @ west haven

Luxe Living! Apt 1 Mi to West Haven Medical Center

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
West Haven
The price is €301
includes taxes & fees
12 Feb - 13 Feb
Luxe Living! Apt 1 Mi to West Haven Medical Center

Cozy Two Bedroom Stay In Downtown New Haven!

Cozy Two Bedroom Stay In Downtown New Haven!
Dwight
10.0 out of 10, Exceptional, (1 review)
"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "
United States
Kimberly S.
The price is €232
includes taxes & fees
12 Feb - 13 Feb
Cozy Two Bedroom Stay In Downtown New Haven!

Family and pet friendly 2-bedroom apartment in the historic section Berlin

Family and pet friendly 2-bedroom apartment in the historic section Berlin
Berlin
Family and pet friendly 2-bedroom apartment in the historic section Berlin

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is €385
includes taxes & fees
2 Mar - 3 Mar
#29 - Modern 5 Bedroom/2 Bath

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, (16 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is €145
includes taxes & fees
18 Feb - 19 Feb
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"We loved this rental. The location is one you might not think is good BUT IT IS. I loved the location. Great coffee shop around the corner. Short walk to great restaurants and it was a safe location. I will stay here again. Also the two bedrooms with two bathrooms is rare and each bedroom with a king bed is super rare. I highly recommend this rental and Joshua was so great and helpful. "
United States
Sharla C.
The price is €287
includes taxes & fees
12 Feb - 13 Feb
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
8.8 out of 10, Excellent, (25 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The Sun Filled Cozy Creamery

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (2 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is €426
includes taxes & fees
14 Feb - 15 Feb
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale

Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
East Shore
10.0 out of 10, Exceptional, (1 review)
"Had a Great stay at the nauti nook!"
United States
David D.
The price is €367
includes taxes & fees
2 Mar - 3 Mar
Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New Britain
7.6 out of 10, Good, (7 reviews)
" Not bad for the price "
United States
Audrey L.
The price is €311
includes taxes & fees
12 Feb - 13 Feb
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is €268
includes taxes & fees
12 Feb - 13 Feb
Newly Remodeled with deck. Close to town center

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.6 out of 10, Exceptional, (7 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
The price is €201
includes taxes & fees
12 Feb - 13 Feb
The Nest At Elm City Flats.
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 €105 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Cheshire Historic District offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, 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 Cheshire Hollow Farm, 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.