An aerial view of a town with a river, buildings, and surrounding greenery.

Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
3 Sep - 4 Sep
Tomorrow
4 Sep - 5 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Chestertown romantic hotels

Sun loungers, beach towels
Smart TV, DVD player, books, video library
Interior
Exterior

1. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
United States
Teresa M.
AED 975
AED 1,980 total
includes taxes & fees
8 Sep - 9 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Marina
Coffee/tea maker, fridge, microwave, oven
1 bedroom, desk, iron/ironing board, WiFi (free)
Smart TV, DVD player

2. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
United States
Tammy
AED 231
AED 853 total
includes taxes & fees
13 Sep - 14 Sep
Cozy Fells Point Gem / In The Heart of Fells Point
Property grounds
Coffee/tea maker, fridge, microwave, oven
Marina
Property grounds

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
United States
Buu T.
AED 1,322
AED 2,345 total
includes taxes & fees
7 Sep - 8 Sep
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina
Coffee/tea maker, fridge, microwave, oven
Exterior detail
Smart TV, books

4. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
United States
Nancy N.
Cozy 2br home w/ parking in downtown Annapolis
On the beach, sun loungers, beach towels
On the beach, sun loungers, beach towels
Interior
Outdoor dining

5. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
AED 2,755
AED 4,865 total
includes taxes & fees
7 Sep - 8 Sep
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Exterior
Interior
Dining
Exterior

6. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
AED 2,938
AED 5,096 total
includes taxes & fees
7 Sep - 8 Sep
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
View all properties

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"My visit was great I have no complaints also the complimentary breakfast was really good alot of options and great food choices in also liked the fact that check out time was at 12 noon I'll definitely stay next time I visit the area thank you"
Iam 1-night trip
Posted 2 days ago
Best Western Plus Hotel & Conference Center
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

8/10 Good
"Only one elevator working and it was the slowest elevator ever, especially since there is only 5 floors! The lobby is bright and welcoming, but the room, while clean, had dark furniture and dark carpeting and are generally just not very bright and cheery. We have stayed here before and had no issues either the room but this time the air conditioner seemed to blow bad smelling air. It might have been due to the standing water on the flat roof outside our window."
Leigh 2-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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 Chestertown Historic District, Northern Chesapeake Bay, or Chesapeake Bay. 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 Chestertown Historic District, Northern Chesapeake Bay, 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 center. If you'd like to explore around the area, consider renting a car to take in more sights.

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