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

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug

Our top choices for Chestertown romantic hotels

Sun loungers, beach towels

1. 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, (155 reviews)
"Kitchen was fully equipped for a large family, beautiful views and perfect family getaway! "
United States
Kshama C.
The price is AED 1,150
AED 2,165 total
includes taxes & fees
1 Sep - 2 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Marina

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (83 reviews)
"Very clean and comfortable home conveniently located near Main St. Great communication as well make this a place I highly recommend!"
United States
Matt R.
The price is AED 1,065
AED 1,939 total
includes taxes & fees
12 Aug - 13 Aug
Cozy 2br home w/ parking in downtown Annapolis
Property grounds

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,469
AED 2,613 total
includes taxes & fees
17 Aug - 18 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina

4. 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, (208 reviews)
"Appreciated the privacy."
United States
Marie
The price is AED 209
AED 815 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Wonderful stay! Excellent location on the water. Had a room with a balcony. Staff and restaurants were all very nice."
Stacey 1-night trip
Posted 3 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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, Rolphs Wharf Marina, 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 Chestertown Historic District, Rolphs Wharf Marina, 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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