An aerial view of a town with a river, buildings, and surrounding greenery.

Find Romantic Hotels in Chestertown, MD from CA $87

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Check availability on Chestertown Romantic Hotels

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chestertown romantic hotels

A two-story house with a covered porch, a staircase, and a garden area.
A garden with a lawn and a table with chairs under a canopy.
A row of stationary bicycles with green frames and white seats, parked outdoors.
A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

1. Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall
United States
Joe
CA $191
CA $212 total
includes taxes & fees
Oct 14 - Oct 15
Haven Point Inn and Gallery
A large, two-story barn-style building with a covered front porch and a garage.
A large, two-story white house with a porch and multiple windows.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

2. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
CA $173
CA $239 total
includes taxes & fees
Oct 28 - Oct 29
Kent Island Resort
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

3. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
United States
Sharon
CA $170
CA $188 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield Inn & Suites by Marriott Middletown
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.
A hotel room with a dining area, a TV, a dresser, and a tray table.
A hotel dining area with a buffet setup, multiple dining tables, chairs, and a ceiling fan.

4. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
United States
Jennifer
CA $144
CA $162 total
includes taxes & fees
Nov 1 - Nov 2
Homewood Suites by Hilton Bel Air
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A traditional house with a covered porch, white picket fence, and lush greenery.

5. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
CA $250
CA $280 total
includes taxes & fees
Oct 18 - Oct 19
Vandiver Inn
A hotel lobby with a reception desk, a coffee station, and a view of the garden through the window.
A hotel lobby with a large entrance, multiple hanging pendant lights, and potted plants.
The exterior of a Hilton Garden Inn with a prominent logo, a brick facade, and large glass doors.
A buffet setup with food and drinks, a fireplace, and a menu sign.

6. Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
Aberdeen
United States
Philip
CA $139
CA $156 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Aberdeen
A modern kitchen with a large island, pendant lights, and a view to the outside.
A golf course with water hazards, surrounded by residential houses.
A row of white single-story houses with dark roofs, a paved driveway, and a grassy lawn.
A covered outdoor seating area with tables and chairs, a pathway leading to it, and a landscaped garden.

7. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
Queenstown
CA $462
CA $527 total
includes taxes & fees
Nov 2 - Nov 3
Queenstown Harbor Golf Resort
A Super 8 hotel with a prominent sign, a large building with multiple windows, and a well-lit entrance.
A kitchen with a dining table and chairs, a microwave, a coffee machine, and a refrigerator.
A bathroom with a shower, toilet, sink, and a mirror.
A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

8. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
Aberdeen
United States
Piyush
CA $78
CA $87 total
includes taxes & fees
Nov 10 - Nov 11
Super 8 by Wyndham Aberdeen MD
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.
A marina with boats docked, a sunset over the water, and trees in the foreground.
A modern living room with a sofa, a wooden coffee table, and a view of the outdoors.
A room with a TV, a plant, a wicker chair, a wooden table, and a view of boats through large windows.

9. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
United States
Maria D.
CA $269
CA $665 total
includes taxes & fees
Oct 18 - Oct 19
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A lobby with a central seating area featuring sofas and armchairs, a coffee table, and potted plants.
A hotel with a modern design, featuring a prominent 'Best Western Plus' sign, a parking area, and a flagpole with a flag.
A hotel dining area with multiple tables and chairs, a kitchen in the background, and a staircase leading to an upper level.
A spacious lobby with a reception desk, seating areas, and large windows offering views of the outdoors.

10. Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center
Medford
United States
Jovaris
CA $158
CA $185 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Plus Hotel & Conference Center
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"all good. Very good when it comes to parking during a boat show."
George 3-night trip
Posted 3 hours ago
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."
Craig 1-night trip
Posted 6 hours ago
The Inn at Chesapeake Bay Beach Club
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"Our stay was quite un eventful and very restful with the following exception; I had checked the wrong date on the arrival and called Expedia to correct it which they said they would do, then beyond that my brother in law passed away and we had to leave a day early, which the hotel was very understanding and only charged for the nights we stayed. BUT Expedia has not refunded any of the excessive charges for either of the two nights involved. They sent a letter saying the hotel would not accept refunding the two nights, which is completely not true as I have a copy of the bill from the hotel and it only covers the two nights we actually spent. At this time I can never trust Expedia again to book anything!"
Steve 3-night trip
Posted 20 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

8/10 Good
"A good location. Many stores and restaurants within walking distance and many more a short drive away."
Justin 2-night trip
Posted 2 days ago
Hampton Inn Baltimore/Glen Burnie

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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