Search Chestertown Flights
Change your flight without a fee on select flights
Money Saving Bundle when you purchase Hotel + Flight!
Get mobile alerts about flight delays, gate changes and more with the FREE Wotif app
Destination airport | Chestertown |
|---|
Need a Car For After Your Flight?
Economy
Chevrolet Spark
Compact
Ford Focus
Midsize
Toyota Corolla
SUV
Jeep Compass
Hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
The price is NZ$206 per night from 3 Aug to 4 Aug
NZ$206
per night
3 Aug - 4 Aug
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (933 reviews)
"Room excellent, very clean, well stocked breakfast, nice outdoor pool with lots of privacy, great restaurants walking distance"
Reviewed on 13 July 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
The price is NZ$262 per night from 23 July to 24 July
NZ$262
per night
23 July - 24 July
Stay at this beach lodge in Chestertown. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive ...
8/10 Very good! (91 reviews)
"We love this place 😀….great pool nice room,free golf!!!!….in the middle of nowhere,but that’s nice…15 minutes to Chestertown…we come every year 👍"
Reviewed on 7 July 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
The price is NZ$139 per night from 21 July to 22 July
NZ$139
per night
21 July - 22 July
Stay at this hotel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. Popular attractions ...
7.2/10 Good! (462 reviews)
"Big room,very comfortable bed,direct tv….pool was out of order,apparently has been for quite a while…..enjoyed our stay😀"
Reviewed on 11 July 2026
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.
Discover top hotels, vacation package, cheap car rental deals and more with Wotif!
More Destinations
- Aberdeen Hotels
- Abingdon Hotels
- Armistead Gardens Hotels
- Atlantis Hotels
- Bayview Hotels
- B&B in Bel Air
- Bel Air Hotels
- Belcamp Hotels
- Bowleys Quarters Hotels
- Brewers Hill Hotels
- Red Carpet Inn Hotels in Canton
- Canton Industrial Area Hotels
- Cedonia Hotels
- Charlestown Hotels
- Chester Hotels
- Chestertown Hotels
- Lodges in Chestertown
- Churchville Hotels
- Curtis Bay Industrial Area Hotels
- Denton Hotels
- Dundalk Marine Terminal Hotels
- Edgewood Hotels
- Hotels near Elk Neck State Park
- Essex Hotels
- Hotels near Fort Smallwood Park
- Frankford Hotels
- Hostels in Gibson Island
- Graceland Park Hotels
- Hotels near Harford Community College
- Havre De Grace Hotels
- Highlandtown Hotels
- Holabird Industrial Park Hotels
- Kresson Hotels
- Lake Shore Hotels
- Marydel Hotels
- Capsule Hotels in Maryland
- B&B in Massey
- Holiday Homes in Massey
- Motels in Massey
- Luxury Hotels in Nottingham
- Pet Friendly Hotels in Nottingham
- Nottingham Hotels
- O'donnell Heights Hotels
- Parkville Hotels
- Pasadena Hotels
- Perryman Hotels
- Hotels near Phillips Army Airfield
- Pomona Hotels
- Port Deposit Hotels
- Marriott Hotels & Resorts in Queenstown
- Queenstown Hotels
- Motels in Queenstown
- Hotels near Queenstown Premium Outlets
- Ridgely Hotels
- Hostels in Rosedale
- Spa Hotels in Rosedale
- Rosedale Hotels
- Rossville Hotels
- Hotels near Sandy Point State Park
- Stevensville Hotels
- Taylor Heights Hotels
- Waltherson Hotels
- Wardour Hotels
- Warwick Hotels
- White Marsh Hotels
- Hotels near White Marsh Mall
- Wye Mills Hotels
- Ace Rental Cars in North East
- Ace Rental Cars in Maryland
- Advantage Rent-A-Car Rental Cars in Greektown
- Car hire near Bay Hills Golf Club
- Car hire near Canton Waterfront Park
- Car hire Church Hill
- Car hire Dundalk
- Car hire near Elk Neck State Park
- Car hire Fallston
- Car hire near Millard Tydings Memorial Park
- Car hire near Queenstown Harbor Golf Club
- Car hire near River Arts Chestertown
- Car hire Rosedale
- Car hire near The Mainstay
- Enterprise Rental Cars in Maryland
^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.