Find Historic Hotels in Chester, CT

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Our top choices for Chester historic hotels

Exterior
Holiday Inn New London - Mystic Area by IHG

Holiday Inn New London - Mystic Area by IHG

Holiday Inn New London - Mystic Area by IHG
3.0 star property
New London
8.4 out of 10, Very Good, (1003)
"The young lady at the front desk that welcomed us was absolutely the best."
United States
Corey
$77 nightly
The price is $89
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn New London - Mystic Area by IHG
Exterior
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (39)
"Great property, would stay here again."
United States
charles b.
$449 nightly
The price is $508
Dec 15 - Dec 16
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Indoor spa tub
The Spa at Norwich Inn

The Spa at Norwich Inn

The Spa at Norwich Inn
3.5 star property
Norwich
8.8 out of 10, Excellent, (1001)
"Great place!"
United States
Jill
$210 nightly
The price is $242
Dec 17 - Dec 18
Total with taxes and fees
The Spa at Norwich Inn
Fridge, microwave, oven, stovetop
Cozy Coastal Cottage New London

Cozy Coastal Cottage New London

Cozy Coastal Cottage New London
New London
9.4 out of 10, Exceptional, (10)
"It was the perfect little place for a night away from the kids. "
United States
Tonya B.
$391 nightly
The price is $442
Dec 15 - Dec 16
Total with taxes and fees
Cozy Coastal Cottage New London
2 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy Upper 2 bedroom apartment >Free Wi-Fi and parking - 2nd floor-private space

Cozy Upper 2 bedroom apartment >Free Wi-Fi and parking - 2nd floor-private space

Cozy Upper 2 bedroom apartment >Free Wi-Fi and parking - 2nd floor-private space
New London
6.6 out of 10, (4)
"Was a great time ."
United States
Linda L.
$232 nightly
The price is $263
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Upper 2 bedroom apartment >Free Wi-Fi and parking - 2nd floor-private space
Interior
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

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.
$511 nightly
The price is $579
Dec 15 - Dec 16
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Terrace/patio
Historic New England home ,Reunions Beach pass

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.
$362 nightly
The price is $410
Dec 22 - Dec 23
Total with taxes and fees
Historic New England home ,Reunions Beach pass
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 Chester Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Holiday family tradition!"
Donald 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

Frequently asked questions

What should a history buff expect from a stay in Chester?
Significant historical sites in Chester are probably at the top of your travel itinerary. You can also discover all there is to see and do such as the waterfront and parks
How many historical hotels will I find in Chester?
In Chester, you'll find 7 hotels and other lodging options bookable on Expedia but not many designated as historic hotels.
What are the must-see historical places and other sights in Chester?
Chester is notable for landmarks like Connecticut Valley Railroad State Park Trail. A couple of additional sights to add to your agenda are Connecticut River and Norma Terris Theater.
What is a historic hotel like in Chester?
By choosing a historic hotel, you can enjoy a vacation in a place that has an official historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel provided that it's a place of special interest. Traditional architecture and period features can be admired in the communal spaces and guestrooms of such hotels in Chester, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. though overall the terms are quite similar. The physical building and architecture of a historic hotel is generally the most significant aspect. For a heritage hotel, often it's the cultural value as well as how it shaped the community.
Do historic hotels in Chester have modern facilities?
Hotels have the safety features and modern conveniences you might expect, though efforts have been made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, 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 choose a historic hotel in Chester, you won't be staying at a place that's uncomfortable for guests or simply rundown.

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