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

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Check availability on Chestertown Luxury Hotels

Tonight
31 Aug - 1 Sept
Tomorrow
1 Sept - 2 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Chestertown luxury hotels

Front of property – evening/night
Lobby sitting area
Garden
Dining

1. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₹20,680
₹25,376 total
includes taxes & fees
28 Sept - 29 Sept
The Inn at Chesapeake Bay Beach Club
Room
Room, 1 King Bed
Exterior
Room, 1 King Bed

2. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
₹19,720
₹22,481 total
includes taxes & fees
8 Sept - 9 Sept
Annapolis Waterfront Hotel, Autograph Collection
Exterior
Interior
Outdoor pool
Restaurant

3. Pendry Baltimore

Pendry Baltimore
Fells Point
  • Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
₹33,194
₹42,927 total
includes taxes & fees
28 Sept - 29 Sept
Pendry Baltimore
View all properties

Top Chestertown Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Very clean staff was nice. Amazing coffee maker in lobby open all the time. The machine grinds the beans fresh with every cup. Major bonus."
Kristina 3-night trip
Posted 10 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"Room was clean. Max, Netflix, Apple+ available besides some channels."
Urserla 1-night trip
Posted 1 day ago
Hampton Inn Baltimore/White Marsh
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"No complaints! Place was clean, felt safe. Staff were great!"
Gary 2-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

8/10 Good
"Location was great, beds were comfortable and the room was clean."
Chris 1-night trip
Posted 2 days ago
Best Western Kent Narrows Inn
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

10/10 Excellent
"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."
Sondra 4-night trip
Posted 4 days ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to Chestertown?
Use Expedia to help you arrange a flight to Baltimore, MD (MTN-Martin State) airport or Easton, MD (ESN-Easton - Newnam) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chestertown offers. During your visit, you might want to enjoy the university which Chestertown is known for.
When can I expect good weather in Chestertown?
Planning for the weather is an important factor for making your trip to Chestertown a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What's there to see and do in Chestertown?
When you're in Chestertown, enjoy exploring the sights and attractions here including Chestertown Historic District, Northern Chesapeake Bay and Chesapeake Bay. If you have extra time while you're in the area, you might want to see Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater.

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