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Check availability on Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (90 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
13 Jul - 14 Jul
The Lodge at Great Oak Landing
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (1,002 reviews)
"The room was very decent and clean. The staff was very helpful. There was little housekeeper service during my 4 day stay"
United States
Anthony
The price is AED 201
AED 225 total
includes taxes & fees
20 Jul - 21 Jul
Super 8 by Wyndham Havre De Grace Aberdeen Area
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (459 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is AED 264
AED 294 total
includes taxes & fees
15 Jul - 16 Jul
Red Roof Inn & Suites Chestertown
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (156 reviews)
"Enjoyed our stay it was very quaint, beautiful surroundings very helpful and friendly staff. We would highly recommend!"
United States
Mercedes
The price is AED 600
AED 791 total
includes taxes & fees
14 Jul - 15 Jul
Kent Island Resort
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (931 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is AED 367
AED 408 total
includes taxes & fees
15 Jul - 16 Jul
Quality Inn Grasonville near Kent Island
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
20 Jul - 21 Jul
Driftwood Inn
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (930 reviews)
"Great visit"
United States
Danielle
The price is AED 379
AED 421 total
includes taxes & fees
2 Aug - 3 Aug
Comfort Inn & Suites Chestertown
Basic Single Room | Premium bedding, down comforters, individually furnished, desk

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (104 reviews)
"Stuff"
United States
matt
The price is AED 290
AED 371 total
includes taxes & fees
13 Jul - 14 Jul
Relax Inn Smyrna Dover Coastal Gateway
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, (616 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
The price is AED 382
AED 428 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (558 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is AED 531
AED 594 total
includes taxes & fees
13 Jul - 14 Jul
Vandiver 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
"Other than the very comfortable beds, the best thing about our stay here is the location. It's an easy 10 minutes walk to the wharf, market space, USNA, state capital, etc. The rooms were very clean and the valet staff was super fast."
Shelley 2-night trip
Posted 11 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.