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Find Historic Hotels in Middletown, CT

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Check availability on Middletown Historic Hotels

Our top choices for Middletown historic hotels

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.
The price is AED 422
AED 1,059 total
includes taxes & fees
10 Dec - 11 Dec
All New Private and Cozy in great location
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
The price is AED 585
AED 672 total
includes taxes & fees
21 Dec - 22 Dec
Omni New Haven Hotel at Yale
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.
The price is AED 345
AED 771 total
includes taxes & fees
10 Dec - 11 Dec
Charming Studio| Near Yale| Downtown New Haven
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.
The price is AED 545
AED 1,051 total
includes taxes & fees
10 Dec - 11 Dec
River Overlook - Check the view from your deck!
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
The price is AED 364
AED 661 total
includes taxes & fees
10 Dec - 11 Dec
Loft apartment in the heart of downtown New Haven and blocks from the Omni Hotel
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Saybrook Manor
9.6 out of 10, Exceptional, (133)
"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "
United States
Rob C.
The price is AED 918
AED 2,128 total
includes taxes & fees
10 Dec - 11 Dec
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
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.
The price is AED 955
AED 1,669 total
includes taxes & fees
10 Dec - 11 Dec
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.
The price is AED 753
AED 1,657 total
includes taxes & fees
8 Jan - 9 January 2026
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
#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 Middletown Hotel Reviews

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

10/10 Excellent
"Yes"
Julieta 1-night trip
Posted 2 days ago
Holiday Inn Cheshire - Southington by IHG

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Frequently asked questions

What should a history enthusiast expect from a trip to Middletown?
You're already probably planning a visit to sights of historical relevance while on vacation in Middletown. You can also enjoy the many sights to visit such as entertainment choices and festivals
How many historical hotels are located in Middletown?
Middletown is home to 22 hotels and other accommodations bookable on Expedia though you won't find many designated historic hotels.
What are the top historical sites and other places to visit in Middletown?
Middletown is notable for landmarks like Wadsworth Mansion, General Mansfield House, and Connecticut Valley Railroad State Park Trail. Favorite family attractions include Kidcity Children's Museum and Van Vleck Observatory. A couple of additional sights to add to your agenda are Connecticut River and Artfarm.
What is a historic hotel like in Middletown?
When you choose a historic hotel, you'll stay in a building that has an officially recognized national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel as long as it has special significance. Traditional architecture and period features can be admired in the guestrooms or communal spaces of these historic hotels in Middletown, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The physical building and architecture of historic hotels tend to be the most significant aspect. For a heritage hotel, it's mainly the cultural value along with how it shaped the community.
Do historic hotels in Middletown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you might expect, though efforts have been made to preserve the historic aspects and traditions. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found at a contemporary hotel will also be available in a historic hotel. Rest assured that when you select a historic hotel in Middletown, you won't be staying at a place that's uncomfortable for guests or simply rundown.