A calm river with boats, wooden docks, and buildings along the shore.

Historic Hotels & Resorts in Chester from AU$357

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Check availability on Chester Historic Hotels

Our top choices for Chester historic hotels

Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is AU$931
includes taxes & fees
27 July - 28 July
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A row of colorful kayaks lined up on a grassy shore by a lake, with a wooden dock extending into the water.

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
9.8 out of 10, Exceptional, (158 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
The price is AU$541
includes taxes & fees
26 July - 27 July
Go Jump in the Lake!
Indoor spa tub

The Spa at Norwich Inn

The Spa at Norwich Inn
3.5 star property
Norwich
8.8 out of 10, Excellent, (1,000 reviews)
"The staff are always go above and beyond, and it is a very clean and comfortable and beautiful place to stay"
United States
Kathryn
The price is AU$357
includes taxes & fees
26 July - 27 July
The Spa at Norwich Inn
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 reviews)
"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 AU$417
includes taxes & fees
12 Aug - 13 Aug
All New Private and Cozy in great location
Exterior

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, (49 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is AU$1,029
includes taxes & fees
27 July - 28 July
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Beach nearby, sun-loungers, beach towels

Charming Carriage House - Beach - Ocean Views - Fireplace

Charming Carriage House - Beach - Ocean Views - Fireplace
New London
10.0 out of 10, Exceptional, (196 reviews)
"Lovely ocean view and great little private beach."
United States
Laura
Charming Carriage House - Beach - Ocean Views - Fireplace
Terrace/patio

Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is AU$895
includes taxes & fees
11 Aug - 12 Aug
Historic New England home ,Reunions Beach pass
Terrace/patio

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Clinton
10.0 out of 10, Exceptional, (30 reviews)
"My family and I really enjoyed our stay here. I would recommend this property & location to others."
United States
Erwin U.
The price is AU$2,434
includes taxes & fees
31 July - 1 Aug
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Smart TV

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
East Lyme
9.8 out of 10, Exceptional, (25 reviews)
"I’ve stayed at this property for 3 summers in a row and every time it has been perfect. Lots of room, very clean and a perfect view!"
United States
Elisa N.
The price is AU$2,434
includes taxes & fees
31 July - 1 Aug
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Friendly staff"
Heather 1-night trip
Posted 13 hours ago
Pier Blue Inn Old Saybrook - Essex

Frequently asked questions

What should a history enthusiast expect from a trip to Chester?
Significant historical sites in Chester are probably at the top of your sightseeing list. Also discover all there is to see and do including the waterfront and parks.
How many historical hotels are located in Chester?
In Chester, you'll find 6 hotels and other lodging options bookable on Expedia though you won't find many designated 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 itinerary are Connecticut River and Chester Creek Marina.
What is a historic hotel like in Chester?
By booking a historic hotel, guests can stay in a place that has an officially recognised historic designation. A palace, castle, stately home or even a lodge, pub or skyscraper can be identified as a historic hotel provided that it has special significance. Traditional architecture and period features can be admired in the public spaces and guestrooms of these historic 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 historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value as well as how it influenced the community.
Do historic hotels in Chester have modern facilities?
Hotel interiors feature the modern conveniences and safety features you've come to expect, while every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities and the usual amenities found in a hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Chester, you won't find a place that is rundown or uncomfortable.

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