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Chestertown Hotel Guide - Historic Hotels in Chestertown, Maryland

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Check availability on Chestertown Historic Hotels

Top Chestertown Historic Hotels

86 State Circle - Luxury Boutique Hotel
Exterior

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is €287
includes taxes & fees
24 Aug - 25 Aug
86 State Circle - Luxury Boutique Hotel
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1835)
"Great stay"
Historic Inns of Annapolis
The Inn at Henderson's Wharf, Ascend Hotel Collection
View from room

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (712)
"Second time staying here - absolutely lovely. "
The price is €153
includes taxes & fees
1 Sept - 2 Sept
The Inn at Henderson's Wharf, Ascend Hotel Collection
Historic Row Home 1 Block from Gate 1 at USNA!
Interior

Historic Row Home 1 Block from Gate 1 at USNA!

10.0 out of 10, Exceptional, (1)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
Historic Row Home 1 Block from Gate 1 at USNA!
Hidden Fells Point Gem / Private Courtyard Patio
Marina

Hidden Fells Point Gem / Private Courtyard Patio

9.6 out of 10, Exceptional, (87)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is €179
includes taxes & fees
20 Aug - 21 Aug
Hidden Fells Point Gem / Private Courtyard Patio
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (193)
"Great place close to eveything"
The price is €179
includes taxes & fees
25 Aug - 26 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is €584
includes taxes & fees
20 Aug - 21 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.4 out of 10, Exceptional, (8)
"Property description is accurate, host is quickly responsive."
The price is €317
includes taxes & fees
20 Aug - 21 Aug
18th Cent. Charm in Historic Downtown Annapolis
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
On the beach, sun-loungers, beach towels

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is €1,216
includes taxes & fees
25 Aug - 26 Aug
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Fridge, microwave, oven, stovetop

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is €1,216
includes taxes & fees
20 Aug - 21 Aug
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
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.

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Excellent hotel"
Francine 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

What should a history buff expect from a stay in Chestertown?
You'll probably want to seek out the places with historical relevance while you're staying in Chestertown. You can also explore the many sights including the sporting events and university setting.
How many historical hotels will I find in Chestertown?
In Chestertown, you'll find 44 lodging options bookable on Expedia though you won't find many designated historic hotels.
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. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater.
What is a historic hotel like in Chestertown?
Guests who choose a historic hotel can enjoy a holiday in a building that has a national historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of such hotels in Chestertown, 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 architecture and building of a historic hotel tends to be what's most significant. For a heritage hotel, it's often the cultural value along with how it shaped the community.
Do historic hotels in Chestertown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, though efforts have been made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found in a hotel will be available in a historic hotel. When you choose a historic hotel in Chestertown, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown.