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

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chestertown romantic hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (997 reviews)
"Good hotel"
United States
Michael
The price is AED 361
AED 400 total
includes taxes & fees
29 Nov - 30 Nov
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 reviews)
"Friendly staff, plenty of parking spaces,family friendly. The building is old but would do some renovation. Furniture needs replacement."
United States
Mary
The price is AED 264
AED 294 total
includes taxes & fees
8 Nov - 9 Nov
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

3. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is AED 233
AED 259 total
includes taxes & fees
1 Nov - 2 Nov
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (124 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is AED 397
AED 454 total
includes taxes & fees
1 Nov - 2 Nov
The Lodge at Great Oak Landing
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Historic authenticity and plaques were very charming. Location was excellent."
Marie 2-night trip
Posted 10 hours ago
Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Easy access to downtown, Great waterside restaurants."
John 1-night trip
Posted 8 days 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 Historical Society of Kent County Maryland, Chestertown Historic District, or Rolphs Wharf Marina. 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 Rolphs Wharf Marina 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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