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Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Chestertown Romantic Hotels

Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (118)
"Great INN super nice staff"
United States
Eric
The price is AED 685
AED 898 total
includes taxes & fees
27 Oct - 28 Oct
Kent Island Resort
Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1854)
"Great location "
United States
Karyl
Historic Inns of Annapolis
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (423)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is AED 712
AED 884 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn
Vandiver Inn
3.5 star property
9.4 out of 10, Exceptional, (525)
"Vandiver Inn was wonderful. Incredibly hospitable and welcoming staff. Lovely room and common areas. Delicious breakfast. I will definitely be visiting again."
United States
Barbara Lindsay
Vandiver Inn
View from room
The Inn at Henderson's Wharf, an Ascend Collection Hotel
The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0 star property
9.2 out of 10, Wonderful, (745)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is AED 531
AED 697 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (28)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Property amenity
Courtyard by Marriott Baltimore Downtown/McHenry Row
Courtyard by Marriott Baltimore Downtown/McHenry Row
3.0 star property
9.0 out of 10, Wonderful, (682)
"Great location "
United States
Kimberley
The price is AED 493
AED 579 total
includes taxes & fees
2 Nov - 3 Nov
Courtyard by Marriott Baltimore Downtown/McHenry Row
Marina
Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (198)
"Great place all around "
United States
Sophia F.
The price is AED 228
AED 751 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Fells Point Gem / In The Heart of Fells Point
Lobby
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center
2.5 star property
7.8 out of 10, Good, (1003)
"Stayed here and went to Lil Duval show, very nice place...would absolutely stay again"
United States
Stacey
The price is AED 392
AED 461 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Hotel & Conference Center
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (872)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is AED 746
AED 851 total
includes taxes & fees
9 Nov - 10 Nov
Annapolis Waterfront Hotel, Autograph 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.
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Top Chestertown Hotel Reviews

Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent
"Perfect stay! from the light lavendar fresh painted walls to the fluffy white bed pillows, it was an excellent choice of hotels to stay. The breakfast room has plenty of room to enjoy the morning freshly grinded and brewed coffee and the variety of breakfast items! Loved the whole hotel experience!"
Dawn 1-night trip
Posted 4 days ago
Garner Hotel Glen Burnie BWI Airport Area by IHG

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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 Historical Society of Kent County Maryland, Rolphs Wharf Marina, 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 Historical Society of Kent County Maryland, Rolphs Wharf Marina, 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.