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Check availability on Chestertown Romantic Hotels

Top Chestertown Romantic Hotels

Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (125)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is 3.302.031 ₫
4.587.925 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (427)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is 4.844.332 ₫
6.047.552 ₫ total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1896)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (876)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is 4.224.386 ₫
4.815.747 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Annapolis Waterfront Hotel, Autograph Collection
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (29)
"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
Property amenity
Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
Locust Point
9.0 out of 10, Wonderful, (694)
"Parking was easy. The property is very nice and the personel very friendly."
United States
Katia
The price is 3.533.535 ₫
4.151.903 ₫ total
includes taxes & fees
24 Nov - 25 Nov
Courtyard by Marriott Baltimore Downtown/McHenry Row
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
Fells Point
9.2 out of 10, Wonderful, (750)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is 3.770.685 ₫
4.954.920 ₫ total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1000)
"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "
United States
Carmen
The price is 3.048.432 ₫
3.581.907 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Hotel & Conference Center
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

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Frequently asked questions

Searching for romantic hotels in Chestertown?
Are you looking for a romantic getaway? You might consider checking out some of the nearby sights and attractions such as Historical Society of Kent County Maryland, Chestertown Historic District or Rolphs Wharf Marina. If you're interested in staying close to a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chestertown?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to do in Chestertown?
There's nothing better than wandering around a new place with your sweetheart, so consider checking out all that Chestertown has to offer. A visit to Historical Society of Kent County Maryland, Chestertown Historic District or Rolphs Wharf Marina might be just the ticket when you're checking out the sights.
What's the best way to get to Chestertown and around town during my romantic getaway?
These transportation options in Chestertown might help your romantic getaway go off without a hitch: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), which is the closest major airport, located 20.3 mi (32.7 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.