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Check availability on Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (934 reviews)
"Room excellent, very clean, well stocked breakfast, nice outdoor pool with lots of privacy, great restaurants walking distance"
United States
Davis
The price is AED 394
AED 437 total
includes taxes & fees
5 Aug - 6 Aug
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (462 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is AED 264
AED 294 total
includes taxes & fees
21 Jul - 22 Jul
Red Roof Inn & Suites Chestertown
Front of property - evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is AED 233
AED 259 total
includes taxes & fees
16 Jul - 17 Jul
Driftwood Inn
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very Good, (91 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is AED 486
AED 556 total
includes taxes & fees
16 Jul - 17 Jul
The Lodge at Great Oak Landing
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,001 reviews)
"It's a smaller hotel but it did the job. The hotel was clean."
United States
Scott
The price is AED 405
AED 449 total
includes taxes & fees
12 Aug - 13 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (618 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
The price is AED 327
AED 366 total
includes taxes & fees
12 Aug - 13 Aug
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Lobby

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,011 reviews)
"We had a very nice stay."
United States
Aimee
The price is AED 351
AED 393 total
includes taxes & fees
19 Jul - 20 Jul
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (787 reviews)
"Good place"
Canada
Uri
The price is AED 621
AED 689 total
includes taxes & fees
23 Jul - 24 Jul
Hyatt Place Kent Narrows & Marina
Exterior

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (702 reviews)
"Very clean enjoyed my stay"
United States
Yahira
The price is AED 353
AED 392 total
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express & Suites Middletown by IHG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 reviews)
"Good hotel for the price"
United States
Brenda
The price is AED 483
AED 536 total
includes taxes & fees
22 Jul - 23 Jul
Best Western Kent Narrows Inn
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
"I enjoyed my beautiful, functional, appropriately sized (i.e., small) room in the stately Maryland House. Though the street outside was bustling, the interior was quiet and peaceful. The staffers I met were lovely and helpful, and everything was tasteful. (Except the lobby coffee. That was godawful.)"
Caroline 1-night trip
Posted 10 hours ago
Historic Inns of Annapolis

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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 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.