Compare Chestertown Guest House Rentals

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Featured Guest Houses in Chestertown

At this guesthouse, guests have access to a garden.

Top Floor East Handicap Accessible features a marina, an outdoor pool, and a gym. There's free parking if you drive. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Pool

Parking included

Guests of Center Parlor Room at Sandy Cove enjoy a marina, an outdoor pool, and a gym. A stay here includes free parking. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Pool

Parking included

Second Floor Standard Deluxe Bay View features a marina, an outdoor pool, and a gym. Free parking is available if you drive. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Pool

Parking included

At Second Floor East Standard Deluxe, guests enjoy a marina, an outdoor pool, and a gym. If you drive, take advantage of free parking. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Pool

Parking included

At First Floor Bay View Deluxe Suite, guests enjoy a marina, an outdoor pool, and a gym. A stay here includes free parking. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Pool

Parking included

Guests of Second Floor Standard Suite Bay View enjoy a marina, an outdoor pool, and a gym. Free parking is included with your stay. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Guests of Top Floor Handicap Accessible Bay View enjoy a marina, an outdoor pool, and a gym. If you drive, put free parking to good use. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

Top Floor Standard Suite features a marina, an outdoor pool, and a gym. Free parking is included with your stay. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.

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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.

Hotel Options in Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

$118

per night

May 15 - May 16

8.4/10 Very Good! (669 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd, Chestertown, MD

$94

per night

May 19 - May 20

7.2/10 Good! (261 reviews)

Historic Inns of Annapolis

58 State Circle, Annapolis, MD

$161

per night

May 28 - May 29

8.8/10 Excellent! (1,608 reviews)

Chestertown Guest Houses essential information

Accommodation	15 Guest Houses
Lowest Price	$94
Highest Price	$161
Popular accommodation	Calico Cottage Guest House, Top Floor East Handicap Accessible, Center Parlor Room at Sandy Cove, Second Floor Standard Deluxe Bay View, Second Floor East Standard Deluxe, First Floor Bay View Deluxe Suite, Second Floor Standard Suite Bay View, Top Floor Handicap Accessible Bay View, Top Floor Standard Suite