Find Historic Hotels in Cheshire, CT

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Our top choices for Cheshire historic hotels

Breakfast and brunch served
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4.0 star property
Downtown New Haven
8.4 out of 10, Very Good, (1007)
"Omni hotel was great. Thanks expedia"
United States
Nancy
$159 nightly
The price is $183
Dec 21 - Dec 22
Total with taxes and fees
Omni New Haven Hotel at Yale
Terrace/patio
The Abner Hotel

The Abner Hotel

3.0 star property
Litchfield Historic District
9.2 out of 10, Wonderful, (46)
"Spacious room and friendly staff "
United States
Frank
$217 nightly
The price is $250
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Abner Hotel
TV
All New Private and Cozy in great location

All New Private and Cozy in great location

Wallingford
8.8 out of 10, Excellent, (6)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
$271 nightly
The price is $288
Dec 10 - Dec 11
Total with taxes and fees
All New Private and Cozy in great location
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven
8.8 out of 10, Excellent, (11)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
$210 nightly
The price is $210
Dec 10 - Dec 11
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Interior
Loft apartment in the heart of downtown New Haven and blocks from the Omni Hotel

Loft apartment in the heart of downtown New Haven and blocks from the Omni Hotel

Downtown New Haven
$159 nightly
The price is $180
Dec 10 - Dec 11
Total with taxes and fees
Loft apartment in the heart of downtown New Haven and blocks from the Omni Hotel
Fridge, microwave, oven, stovetop
River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!

Collinsville
10.0 out of 10, Exceptional, (23)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
$253 nightly
The price is $286
Dec 10 - Dec 11
Total with taxes and fees
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville
10.0 out of 10, Exceptional, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
$401 nightly
The price is $454
Dec 10 - Dec 11
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop
Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass

Guilford
9.2 out of 10, Wonderful, (90)
"The location of this place is best!"
United States
Dr. Maureen C.
$381 nightly
The price is $432
Jan 1 - Jan 2, 2026
Total with taxes and fees
Historic New England home ,Reunions Beach pass
Fridge, microwave, oven, stovetop
#25 *Massive* 5 BR in Downtown Southington*

#25 *Massive* 5 BR in Downtown Southington*

Southington
8.8 out of 10, Excellent, (3)
"The property was perfect for my family and I. "
United States
Marguerite
$519 nightly
The price is $562
Dec 27 - Dec 28
Total with taxes and fees
#25 *Massive* 5 BR in Downtown Southington*
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 Hotel Reviews

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"Located in a safe and quiet area of Hartford and the staff was very friendly and professional so my only complaint was the carpet and sofa bed were a little outdated but overall I would definitely come back here. Keep up the great work "
Jonathan 2-night trip
Posted 2 days ago
Hampton Inn & Suites Hartford/East Hartford

Frequently asked questions

What should a history enthusiast expect from a trip to Cheshire?
You'll probably want to seek out the sights of historical relevance during your trip to Cheshire. Why not absorb the local color with a visit to the restaurants?
How many historical hotels are there in Cheshire?
Cheshire is home to 5 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the most important historical places and other sights in Cheshire?
Favorite places to visit include Barker Character, Comic and Cartoon Museum, Cheshire Hollow Farm, and Maplecroft Plaza Shopping Center. A couple of additional sights to add to your agenda are Drazen Orchards and Bartlem Park.
What is a historic hotel like in Cheshire?
By choosing a historic hotel, you can spend a night or two someplace that has an officially recognized national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be turned into a historic hotel provided that it has special significance. Traditional architecture and period features are often preserved within the guestrooms or public spaces of these historic hotels in Cheshire, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value as well as how it inspired the community.
Do historic hotels in Cheshire have modern facilities?
Hotels include modern conveniences and safety features you expect to find, though efforts have been made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the popular amenities found in most hotels should be available at a historic hotel. Rest assured that when you select a historic hotel in Cheshire, you won't find yourself staying at a place that's uncomfortable for guests or simply rundown.

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