Compare Chestertown Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Chestertown
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville MD
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include local meal delivery service, a garden, and barbecue grills.
Pool
Hot Tub
Second Floor East Standard Deluxe
60 Sandy Cove Road North East MD
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
Top Floor Family Deluxe Bay View
60 Sandy Cove Road North East MD
Top Floor Family Deluxe Bay View features a marina, an outdoor pool, and a gym. You can take advantage of free parking if you drive. Additional amenities include an outdoor tennis court, an arcade/game room, and a convenience store.
Pool
Parking included
Top Floor East Handicap Accessible
60 Sandy Cove Road North East MD
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
Top Floor Standard Suite
60 Sandy Cove Road North East MD
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.
Pool
Parking included
The Shallow Creek Shore Shack on the Chesapeake Bay
Sparrows Point MD
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
First Floor Family Deluxe Suite
60 Sandy Cove Road North East MD
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
Second Floor Standard Deluxe Bay View
60 Sandy Cove Road North East MD
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
First Floor Bay View Deluxe Suite
60 Sandy Cove Road North East MD
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
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
$101 nightly
The price is $112 total per night from Feb 25 to Feb 26
$112 total
Feb 25 - Feb 26
Total with taxes and fees
8.4/10 Very Good! (870 reviews)
Historic Inns of Annapolis
58 State Circle Annapolis MD
$229 nightly
The price is $261 total per night from Feb 26 to Feb 27
$261 total
Feb 26 - Feb 27
Total with taxes and fees
9/10 Wonderful! (1,879 reviews)
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
$65 nightly
The price is $75 total per night from Feb 8 to Feb 9
$75 total
Feb 8 - Feb 9
Total with taxes and fees
7/10 Good! (1,149 reviews)
Chestertown Guest Houses essential information
Accommodation | 16 Guest Houses |
|---|---|
Lowest Price | $75 |
Highest Price | $261 |
Popular accommodation | Island Life! Kent Island Waterfront with Pool-Bring your boat!, Second Floor East Standard Deluxe, Top Floor Family Deluxe Bay View, Top Floor East Handicap Accessible, Top Floor Standard Suite, The Shallow Creek Shore Shack on the Chesapeake Bay, First Floor Family Deluxe Suite, Second Floor Standard Deluxe Bay View, First Floor Bay View Deluxe Suite |