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Chestertown Romantic Hotel

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Check availability on Chestertown Romantic Hotel

Top Chestertown Romantic Hotel

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is HK$1,446
HK$1,778 total
includes taxes & fees
29 Sept - 30 Sept
Inn at Haven Harbour
Vandiver Inn
Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (518)
"Been to the Vandiver many times and are always pleasantly pleased."
Vandiver Inn
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, (419)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is HK$1,595
HK$1,968 total
includes taxes & fees
26 Oct - 27 Oct
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 HK$1,470
HK$1,924 total
includes taxes & fees
1 Oct - 2 Oct
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, (664)
"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 HK$1,043
HK$1,225 total
includes taxes & fees
19 Oct - 20 Oct
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, (1853)
"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, (1001)
"Free breakfast is definitely a plus."
The price is HK$900
HK$1,057 total
includes taxes & fees
29 Sept - 30 Sept
Best Western Plus Hotel & Conference Center
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, (196)
"Great place close to eveything"
The price is HK$482
HK$1,590 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Fells Point Gem / In The Heart of Fells Point
The Inn at Henderson's Wharf, an Ascend Collection Hotel
View from room

The Inn at Henderson's Wharf, an Ascend Collection Hotel

3.0 star property
9.2 out of 10, Wonderful, (728)
"Clean, convenient, personable staff."
The price is HK$1,225
HK$1,594 total
includes taxes & fees
29 Sept - 30 Sept
The Inn at Henderson's Wharf, an Ascend Collection Hotel
5-bedroom vacation home 5 minutes from historic Charlestown
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (144)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is HK$2,316
HK$4,425 total
includes taxes & fees
30 Sept - 1 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
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
"The staff were professional and friendly. "
Karen 3-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 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 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 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 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 centre. If you'd like to explore around the area, consider renting a car to explore more sights.