Cheshire Historic District Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Cheshire Historic District vacation rentals

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)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
$226 nightly
The price is $256
Feb 23 - Feb 24
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "
United States
Robb F.
$305 nightly
The price is $326
Feb 22 - Feb 23
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
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.
$271 nightly
The price is $288
Feb 17 - Feb 18
Total with taxes and fees
All New 1BR with tons of Charm
Interior

New England Tiny Home Experience: Coffee & More!

New England Tiny Home Experience: Coffee & More!
3.0 star property
Main Street Historic District
$290 nightly
The price is $334
Feb 18 - Feb 19
Total with taxes and fees
New England Tiny Home Experience: Coffee & More!
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
$304 nightly
The price is $345
Feb 17 - Feb 18
Total with taxes and fees
Angelica’s safe haven @ west haven
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.
$257 nightly
The price is $267
Feb 18 - Feb 19
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
2 bedrooms, WiFi, bed sheets

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.
$238 nightly
The price is $270
Feb 18 - Feb 19
Total with taxes and fees
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
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.
$182 nightly
The price is $206
Feb 17 - Feb 18
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Smart TV

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (5 reviews)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
United States
Amal A.
$133 nightly
The price is $149
Feb 24 - Feb 25
Total with taxes and fees
Cozy East Haven Home • Near Beach & Yale
Exterior

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.
$197 nightly
The price is $223
Feb 24 - Feb 25
Total with taxes and fees
Family Stays: Middletown, CT
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)
"Everything was great and just as charming as the photo indicated. "
United States
Nancy F.
$232 nightly
The price is $252
Feb 17 - Feb 18
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
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
$191 nightly
The price is $216
Feb 17 - Feb 18
Total with taxes and fees
Cozy Guest Suite in Historic Home
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$107 nightly
The price is $121
Feb 17 - Feb 18
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
$325 nightly
The price is $349
Mar 7 - Mar 8
Total with taxes and fees
#23 *COMFORT & LUXURY* 3 BR/2 BA House
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
$134 nightly
The price is $151
Feb 17 - Feb 18
Total with taxes and fees
One private bedroom with work space and shared home with spa.
Private kitchen

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.
$376 nightly
The price is $425
Feb 17 - Feb 18
Total with taxes and fees
Welcoming 4-bedroom house in charming Hamden
1 bedroom, iron/ironing board, WiFi, bed sheets

Downtown New Haven Escape

Downtown New Haven Escape
Dwight
8.0 out of 10, Very Good, (6 reviews)
"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.
$244 nightly
The price is $252
Feb 17 - Feb 18
Total with taxes and fees
Downtown New Haven Escape
Desk, WiFi

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
$399 nightly
The price is $426
Feb 19 - Feb 20
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat | Fire Pit
Fridge, microwave, oven, stovetop

All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
$271 nightly
The price is $288
Feb 23 - Feb 24
Total with taxes and fees
All New Studio apartment in center of town
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)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
$485 nightly
The price is $516
Feb 23 - Feb 24
Total with taxes and fees
The Jewel of The Cove - Historic Coastal Retreat
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Historic District Hotel Reviews

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

10/10 Excellent
"Yes"
Yasar 2-night trip
Posted 3 days ago
Holiday Inn Cheshire - Southington by IHG

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire Historic District vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire Historic District vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cheshire Historic District in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation 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 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 Roaring Brook Park. 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.