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Check availability on Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

Marina

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (205 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is AED 209
AED 823 total
includes taxes & fees
25 May - 26 May
Cozy Fells Point Gem / In The Heart of Fells Point
Sun loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (152 reviews)
"This is the second time my group of friends has stayed here. The house is very comfortable and well-appointed, and the view is gorgeous! "
United States
Melinda S.
The price is AED 1,045
AED 2,038 total
includes taxes & fees
27 May - 28 May
5-bedroom vacation home 5 minutes from historic Charlestown
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 771
AED 1,566 total
includes taxes & fees
25 May - 26 May
Cozy 2br home w/ parking in downtown Annapolis
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
21 May - 22 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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.
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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Yes"
Cleopetra 1-night trip
Posted 20 hours ago
Pendry Baltimore

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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 Rolphs Wharf Marina, 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 Rolphs Wharf Marina, 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.