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Search Romantic Hotels in Chestertown

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Check availability on Chestertown Romantic Hotels

Tonight
1 Nov - 2 Nov
Tomorrow
2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Top Chestertown Romantic Hotels

Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1872)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (423)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is ฿5,981
฿7,461 total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (123)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
United States
Chi
The price is ฿5,653
฿7,471 total
includes taxes & fees
2 Nov - 3 Nov
Kent Island Resort
Property amenity
Courtyard by Marriott Baltimore Downtown/McHenry Row
Courtyard by Marriott Baltimore Downtown/McHenry Row
3.0 star property
9.0 out of 10, Wonderful, (689)
"Great location "
United States
Kimberley
The price is ฿4,047
฿4,755 total
includes taxes & fees
10 Nov - 11 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
9.2 out of 10, Wonderful, (746)
"Beautiful location and a great stay. Eric at the front desk was great!"
United States
dena
The price is ฿4,369
฿5,777 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
7.8 out of 10, Good, (1001)
"Great stay"
United States
Diedre
The price is ฿3,740
฿4,395 total
includes taxes & fees
9 Nov - 10 Nov
Best Western Plus Hotel & Conference Center
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (28)
"Very friendly staff!"
United States
Richard
134 Prince - Luxury Boutique Hotel
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
8.8 out of 10, Excellent, (873)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is ฿6,568
฿7,487 total
includes taxes & fees
9 Nov - 10 Nov
Annapolis Waterfront Hotel, Autograph Collection
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again "
Jannelle 2-night trip
Posted 6 days ago
Best Western Plus Hotel & Conference Center

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, Rolphs Wharf Marina or Chesapeake Bay. 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, Rolphs Wharf Marina or Chesapeake Bay 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.