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

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Check availability on Chestertown Romantic Hotels

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Chestertown romantic hotels

Free daily full breakfast

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (943 reviews)
"Clean and affordable amenities and a decent breakfast!"
United States
Deanna
The price is AED 394
AED 437 total
includes taxes & fees
25 Aug - 26 Aug
Comfort Inn & Suites Chestertown
Lobby lounge

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (470 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is AED 231
AED 257 total
includes taxes & fees
10 Aug - 11 Aug
Red Roof Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very Good, (94 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 397
AED 454 total
includes taxes & fees
6 Aug - 7 Aug
The Lodge at Great Oak Landing
Front of property - evening/night

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (178 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is AED 233
AED 259 total
includes taxes & fees
5 Aug - 6 Aug
Driftwood Inn
Desk, laptop workspace, iron/ironing board, WiFi (free)

5. Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,004 reviews)
"Great place for an overnight stay"
United States
Chrystal
The price is AED 312
AED 347 total
includes taxes & fees
6 Aug - 7 Aug
Quality Inn Smyrna
Basic Single Room | Premium bedding, down comforters, desk, laptop workspace

6. Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (108 reviews)
"Clean, great staff, and accessible parking."
United States
Ashley
The price is AED 327
AED 418 total
includes taxes & fees
5 Aug - 6 Aug
Relax Inn Smyrna Dover Coastal Gateway
Exterior

7. 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, (710 reviews)
"Very clean enjoyed my stay"
United States
Yahira
The price is AED 371
AED 412 total
includes taxes & fees
23 Aug - 24 Aug
Holiday Inn Express & Suites Middletown by IHG
Indoor pool

8. Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (913 reviews)
"Room was clean and nice. Breakfast is mid can do better with that"
United States
Delaine
The price is AED 383
AED 425 total
includes taxes & fees
1 Sep - 2 Sep
Hampton Inn Middletown
Property amenity

9. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (413 reviews)
"Always a great place to stay"
United States
James
The price is AED 437
AED 485 total
includes taxes & fees
9 Aug - 10 Aug
Fairfield Inn & Suites by Marriott Middletown
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), bed sheets

10. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (947 reviews)
"Great staff and breakfast crew. Extremely reasonable price, for convenient location."
United States
Jonathan
The price is AED 372
AED 413 total
includes taxes & fees
1 Sep - 2 Sep
Quality Inn Grasonville near Kent Island
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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"The proximity to the road sometimes makes the location noisy. But the friendliness of the staff, complement this noise disturbance"
Modupe 1-night trip
Posted 10 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Wonderful stay! Excellent location on the water. Had a room with a balcony. Staff and restaurants were all very nice."
Stacey 1-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 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.

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