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
15 Sep - 16 Sep
Tomorrow
16 Sep - 17 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Chestertown romantic hotels

Marina
Coffee/tea maker, fridge, microwave, oven
Smart TV, DVD player
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 776 total
includes taxes & fees
21 Sep - 22 Sep
Cozy Fells Point Gem / In The Heart of Fells Point
Sun loungers, beach towels
Interior
Smart TV, DVD player, books, video library
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 1,921 total
includes taxes & fees
16 Sep - 17 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Property grounds
Marina
Interior
Property grounds

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
United States
Buu T.
AED 1,322
AED 2,441 total
includes taxes & fees
16 Sep - 17 Sep
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina
Coffee/tea maker, fridge, microwave, oven
Smart TV, books
Exterior detail

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
22 Sep - 23 Sep
Cozy 2br home w/ parking in downtown Annapolis
Exterior
Interior
Exterior
Dining

5. 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
16 Sep - 17 Sep
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
On the beach, sun loungers, beach towels
On the beach, sun loungers, beach towels
Interior
Interior

6. 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 2,935
AED 5,084 total
includes taxes & fees
16 Sep - 17 Sep
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"This is a great hotel in a great location two great restaurants."
William 1-night trip
Posted 14 hours ago
Annapolis Waterfront Hotel, Autograph Collection
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"The room was clean and spacious, the breakfast had a good variety and was hot."
Carl 2-night trip
Posted 15 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Beautiful hotel. Very clean and nicely decorated. Staff very friendly"
Carter 3-night trip
Posted 1 day ago
Pendry Baltimore
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"The place was very quiet and not a lot going on. So if you like a more relaxed hotel, this is the place for you"
Christopher 3-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Baltimore North, MD

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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