Chestertown hotels

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Chestertown, MD
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Good to know

Low season

November Cheapest month to stay with an average 12% drop in price.

High season

September Most expensive month to stay with an average 67% rise in price.

Average price (weeknight)

$134 Average Sun - Thu price over the last 2 weeks.

Average price (weekend night)

$191 Average Fri & Sat price over the last 2 weeks.

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Where to stay in Chestertown?

Our Heatmaps tool will help you find the perfect place to stay in Chestertown by showing you how close hotel options are to major activities
Best Chestertown hotels

Most recommended Chestertown hotels

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Holiday Inn Express Hotel & Suites Chestertown - Chestertown - Bedroom
When you stay at Holiday Inn Express Hotel & Suites Chestertown in Chestertown, you'll be 12 minutes by foot from Washington College. Featured amenities include a business center, complimentary newspapers in the lobby, and a 24-hour front desk. Free self parking is available onsite.
Free Wi-Fi
Pet friendly
Check availability
Check availability
Quality Suites - Chestertown - Building
Quality Suites
7.2 Good
$87+
$87+
Get more value for your hard-earned money at the 100 percent smoke-free Quality Suites hotel in Chestertown, MD, which lets you relax and focus on the people and experiences that you came for. We are near Washington College, Chesapeake College, Betterton Beach and Eastern Neck Wildlife Refuge. Amenities include free WiFi, free ample parking, free hot breakfast, free coffee, free weekday newspaper, meeting room, indoor heated pool, sundeck and guest laundry facilities. Guest rooms feature a coffee maker, hair dryer, HDTV, premium bedding, iron and ironing board. Also, earn rewards including free nights and gift cards with our Choice Privileges Rewards program.
Free Wi-Fi
Pool
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Driftwood Inn - Chestertown - Building
Driftwood Inn
6.7 Good
$72+
$72+
When you stay at Driftwood Inn in Chestertown, you'll be 5 minutes by foot from Washington College. Free self parking is available onsite.
Free Wi-Fi
Pet friendly
Check availability
Check availability
Brampton Bed and Breakfast Inn - Chestertown - Building
Brampton Bed and Breakfast Inn
9.8 Excellent
$287+
$287+
The Brampton Bed and Breakfast Inn provides a great place for travelers to relax after a busy day. The hotel is located close to many of Chestertown's attractions including Schooner Sultana and Kent County Visitors Center. In their spare time, guests can explore the hotel's surroundings. There's never a dull moment at this hotel, our guests indicate that the facilities are excellent.
Free Wi-Fi
Check availability
Check availability

Best rooms in Chestertown

Brampton Bed and Breakfast Inn - Chestertown - Building
Brampton Bed and Breakfast Inn
9.8 Excellent
$287+
$287+
The Brampton Bed and Breakfast Inn provides a great place for travelers to relax after a busy day. The hotel is located close to many of Chestertown's attractions including Schooner Sultana and Kent County Visitors Center. In their spare time, guests can explore the hotel's surroundings. There's never a dull moment at this hotel, our guests indicate that the facilities are excellent.
Free Wi-Fi
Check availability
Check availability
Great Oak Manor - Chestertown - Outdoors view
Great Oak Manor
9.6 Excellent
$231+
$231+
With a stay at Great Oak Manor in Chestertown, you'll be next to a golf course, and 9.1 mi (14.6 km) from Washington College and 12.6 mi (20.2 km) from Rock Hall Harbor. Featured amenities include luggage storage, laundry facilities, and a library. Free self parking is available onsite.
Free Wi-Fi
Pet friendly
Spa
Check availability
Check availability
Holiday Inn Express Hotel & Suites Chestertown - Chestertown - Bedroom
When you stay at Holiday Inn Express Hotel & Suites Chestertown in Chestertown, you'll be 12 minutes by foot from Washington College. Featured amenities include a business center, complimentary newspapers in the lobby, and a 24-hour front desk. Free self parking is available onsite.
Free Wi-Fi
Pet friendly
Check availability
Check availability
Driftwood Inn - Chestertown - Building
Driftwood Inn
6.7 Good
$72+
$72+
When you stay at Driftwood Inn in Chestertown, you'll be 5 minutes by foot from Washington College. Free self parking is available onsite.
Free Wi-Fi
Pet friendly
Check availability
Check availability