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
13 Sep - 14 Sep
Tomorrow
14 Sep - 15 Sep
Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep

Our top choices for Chestertown romantic hotels

Marina
Coffee/tea maker, fridge, microwave, oven
Exterior detail
1 bedroom, desk, iron/ironing board, WiFi (free)

1. 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 191
AED 802 total
includes taxes & fees
21 Sep - 22 Sep
Cozy Fells Point Gem / In The Heart of Fells Point
Sun loungers, beach towels
Interior
Exterior
5 bedrooms, iron/ironing board, WiFi (free), bed sheets

2. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
United States
Teresa M.
AED 945
AED 1,933 total
includes taxes & fees
16 Sep - 17 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Property grounds
Property grounds
Marina
Interior

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
United States
Buu T.
AED 1,322
AED 2,332 total
includes taxes & fees
14 Sep - 15 Sep
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina
Smart TV, books
Exterior detail
Coffee/tea maker, fridge, microwave, oven

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
United States
Nancy N.
AED 826
AED 1,633 total
includes taxes & fees
14 Sep - 15 Sep
Cozy 2br home w/ parking in downtown Annapolis
On the beach, sun loungers, beach towels
Outdoor dining
Interior
On the beach, sun loungers, beach towels

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 4,849 total
includes taxes & fees
16 Sep - 17 Sep
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Exterior
Interior
Dining
Exterior

6. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
AED 2,935
AED 5,084 total
includes taxes & fees
14 Sep - 15 Sep
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
View all properties

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Property was a historical renovation which is very well done. Best part was location. A bit pricey and we didn’t need or use the complimentary bottle of wine. Bottled water would have been preferred. Staff and housekeeping was great. Coffee was available, but no food service for breakfast."
Charles 2-night trip
Posted 15 hours ago
Historic Inns of Annapolis
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Best hotel in Fells Point, hands down!"
Charles 3-night trip
Posted 18 hours ago
Pendry Baltimore

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, Chestertown Historic District, or Northern 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 Historical Society of Kent County Maryland, Chestertown Historic District, or Northern 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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