Compare Chestertown Guest House Rentals
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Featured Guest Houses in Chestertown
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include local meal delivery service, barbecue grills, and a garden.
Pool
Hot Tub
Calico Cottage Guest House
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Air conditioning
Parking available
Top Floor East Handicap Accessible
60 Sandy Cove Road, North East, MD
The price is $499 per night
$499
includes taxes & fees
$471 per night
May 4 - May 5
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
Center Parlor Room at Sandy Cove
60 Sandy Cove Road, North East, MD
The price is $527 per night
$527
includes taxes & fees
$497 per night
May 6 - May 7
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
First Floor Bay View Deluxe Suite
60 Sandy Cove Road, North East, MD
The price is $569 per night
$569
includes taxes & fees
$537 per night
May 11 - May 12
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
Top Floor Deluxe Suite Bay View
60 Sandy Cove Road, North East, MD
The price is $569 per night
$569
includes taxes & fees
$537 per night
May 26 - May 27
At Top Floor Deluxe Suite Bay View, guests enjoy a marina, an outdoor pool, and a gym. You can put free parking to good use if you drive. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.
Pool
Parking included
Top Floor Handicap Accessible Bay View
60 Sandy Cove Road, North East, MD
The price is $527 per night
$527
includes taxes & fees
$497 per night
May 14 - May 15
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.
Pool
Parking included
First Floor Family Deluxe Suite
60 Sandy Cove Road, North East, MD
The price is $499 per night
$499
includes taxes & fees
$471 per night
May 4 - May 5
Guests of First Floor Family Deluxe Suite enjoy 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
Top Floor Standard Deluxe
60 Sandy Cove Road, North East, MD
The price is $499 per night
$499
includes taxes & fees
$471 per night
May 6 - May 7
At Top Floor Standard Deluxe, guests enjoy a marina, an outdoor pool, and a gym. You can put free parking to good use if you drive. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.
Pool
Parking included
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
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
The price is $76 per night from May 7 to May 8
$76
includes taxes & fees
$68 per night
May 7 - May 8
7.2/10 Good! (345 reviews)
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is $122 per night from May 7 to May 8
$122
includes taxes & fees
$110 per night
May 7 - May 8
8.4/10 Very Good! (758 reviews)
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
The price is $163 per night from May 6 to May 7
$163
includes taxes & fees
$147 per night
May 6 - May 7
7.6/10 Good! (48 reviews)
Chestertown Guest Houses essential information
Accommodation | 16 Guest Houses |
|---|---|
Lowest Price | $76 |
Highest Price | $569 |
Popular accommodation | Island Life! Kent Island Waterfront with Pool-Bring your boat!, Calico Cottage Guest House, Top Floor East Handicap Accessible, Center Parlor Room at Sandy Cove, First Floor Bay View Deluxe Suite, Top Floor Deluxe Suite Bay View, Top Floor Handicap Accessible Bay View, First Floor Family Deluxe Suite, Top Floor Standard Deluxe |
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