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Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Top Chestertown Romantic Hotels

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.6 out of 10, Excellent, (4)
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "
The price is NT$6,369
NT$7,744 total
includes taxes & fees
Oct 5 - Oct 6
Inn at Haven Harbour
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (420)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is NT$5,930
NT$7,356 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is NT$5,747
NT$7,522 total
includes taxes & fees
Oct 21 - Oct 22
Kent Island Resort
Courtyard by Marriott Baltimore Downtown/McHenry Row
Property amenity

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
9.0 out of 10, Wonderful, (671)
"I liked that it was conveniently next to a grocery store. I also liked that the rooms were spacious and appeared to be soundproof. "
The price is NT$4,078
NT$4,792 total
includes taxes & fees
Oct 19 - Oct 20
Courtyard by Marriott Baltimore Downtown/McHenry Row
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1832)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1005)
"Great stay"
The price is NT$3,247
NT$3,816 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Hotel & Conference Center
134 Prince - Luxury Boutique Hotel
Exterior

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (26)
"Very friendly staff!"
134 Prince - Luxury Boutique Hotel
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.
View all properties

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Great stay"
Diedre 2-night trip
Posted 3 days ago
Best Western Plus Hotel & Conference Center

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Frequently asked questions

Searching for romantic hotels in Chestertown?
Are you looking for a romantic vacation? You might consider checking out some of the nearby sights and attractions such as Historical Society of Kent County Maryland, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, 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, check out these details about year-round temperatures in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to do in Chestertown?
There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Chestertown has to offer. A visit to Historical Society of Kent County Maryland, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater 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 center. If you'd like to explore around the area, consider renting a car to take in more sights.