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Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Top Chestertown Romantic Hotels

Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (856)
" Very clean, spacious room, friendly staff"
The price is NT$7,114
NT$8,109 total
includes taxes & fees
Aug 24 - Aug 25
Annapolis Waterfront Hotel, Autograph Collection
134 Prince - Luxury Boutique Hotel
Exterior

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (24)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
134 Prince - Luxury Boutique Hotel
The Inn at Henderson's Wharf, Ascend Hotel Collection
View from room

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (712)
"Second time staying here - absolutely lovely. "
The price is NT$4,059
NT$5,367 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Henderson's Wharf, Ascend Hotel Collection
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.

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Excellent hotel"
Francine 2-night trip
Posted 2 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, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater. 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.
What's the best hotel for couples in Chestertown?
Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking.
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, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater 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.