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Find Historic Hotels in Chestertown, MD

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Check availability on Chestertown Historic Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Chestertown Historic Hotels

Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1854)
"Great location "
United States
Karyl
Historic Inns of Annapolis
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (28)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
View from room
The Inn at Henderson's Wharf, an Ascend Collection Hotel
The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0 star property
9.2 out of 10, Wonderful, (745)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is AED 531
AED 697 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Marina
Hidden Fells Point Gem / Private Courtyard Patio
Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (88)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is AED 228
AED 755 total
includes taxes & fees
2 Nov - 3 Nov
Hidden Fells Point Gem / Private Courtyard Patio
Marina
Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (198)
"Great place all around "
United States
Sophia F.
The price is AED 228
AED 751 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Fells Point Gem / In The Heart of Fells Point
Fridge, microwave, oven, stovetop
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
9.8 out of 10, Exceptional, (65)
"Cute and quiet neighborhood with a beautiful view of the park. The host made it a stress free stay with great tips."
United States
Anonymous traveler
The price is AED 544
AED 1,044 total
includes taxes & fees
2 Nov - 3 Nov
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Marina
Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
United States
Vincent W.
The price is AED 430
AED 1,135 total
includes taxes & fees
3 Nov - 4 Nov
Cozy 2br home w/ parking in downtown Annapolis
Exterior
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique Hotel
2.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is AED 1,171
AED 1,334 total
includes taxes & fees
27 Oct - 28 Oct
86 State Circle - Luxury Boutique Hotel
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
Pendry Baltimore
Pendry Baltimore
5.0 star property
9.4 out of 10, Exceptional, (1000)
"Great hotel"
United States
kimberly
The price is AED 1,175
AED 1,532 total
includes taxes & fees
17 Nov - 18 Nov
Pendry Baltimore
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
27 Oct - 28 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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 Chestertown Hotel Reviews

Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent
"Perfect stay! from the light lavendar fresh painted walls to the fluffy white bed pillows, it was an excellent choice of hotels to stay. The breakfast room has plenty of room to enjoy the morning freshly grinded and brewed coffee and the variety of breakfast items! Loved the whole hotel experience!"
Dawn 1-night trip
Posted 4 days ago
Garner Hotel Glen Burnie BWI Airport Area by IHG

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Frequently asked questions

What can I expect on my historical trip to Chestertown?
You'll probably want to seek out the places with historical relevance during your vacation in Chestertown. You can also enjoy the many sights including the sporting events and university setting
How many historical hotels will I find in Chestertown?
Chestertown is home to 38 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the must-see historical places and other sights to visit in Chestertown?
Chestertown is notable for landmarks like Historical Society of Kent County Maryland. The picturesque setting of Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater.
What is a historic hotel like in Chestertown?
When you choose a historic hotel, you'll stay someplace that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel as long as it has special significance. Traditional architecture and period features can be admired within the guestrooms or public spaces of these historic hotels in Chestertown, 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. but overall the terms are quite similar. The architecture and actual building of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value and how it influenced the community.
Do historic hotels in Chestertown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found at a contemporary hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Chestertown, you won't find yourself staying at a place that's uncomfortable or rundown.