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

Find Romantic Hotels in Chestertown, MD

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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
26 Aug - 27 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, (471 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
Front of property - evening/night

3. 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
Private beach nearby, sun loungers, beach volleyball

4. 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
9 Aug - 10 Aug
The Lodge at Great Oak Landing
Exterior

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.8 out of 10, Exceptional, (9 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is AED 440
AED 489 total
includes taxes & fees
5 Aug - 6 Aug
Haven Point Inn and Gallery
Lake

6. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (69 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is AED 663
AED 736 total
includes taxes & fees
5 Aug - 6 Aug
Inn at Huntingfield Creek
Exterior

7. 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, (1,004 reviews)
"Very clean hotel,beautiful view and great staff."
United States
Jackie
The price is AED 433
AED 481 total
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby lounge

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (893 reviews)
"The was very clean."
United States
KaTerra
The price is AED 393
AED 454 total
includes taxes & fees
9 Aug - 10 Aug
SpringHill Suites Baltimore White Marsh/Middle River
Terrace/patio

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (799 reviews)
"Great location"
United States
jeanette
The price is AED 621
AED 689 total
includes taxes & fees
16 Aug - 17 Aug
Hyatt Place Kent Narrows & Marina
Exterior

10. 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, (629 reviews)
"Very clean room. Good breakfast. Friendly staff. Very convenient to I-95. Would return."
United States
Carolyn
The price is AED 305
AED 341 total
includes taxes & fees
1 Sep - 2 Sep
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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

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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