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We offer guests outstanding service and a comfortable stay all at the most affordable prices in town. We are the most budget friendly motel in town to give you the most bang for your buck while visiting Chestertown. This 28-room Inn conveniently located in peaceful Chestertown, a historic colonial town by the sparkling waters of the Chester River. This motel is located just within walking distance from Washington College. It offers free Wi-Fi and a 24-hour front desk. Downtown Chestertown, Maryland is 1 mile from the motel. The Driftwood Inn has colonial rooms decorated in rustic wood and soft neutral colors. All rooms include a cable TV with HBO channels, a microwave, refrigerator, and free parking right in front of your room.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Non-smoking hotel
Pets Allowed ( Dog / Pet Friendly )
Public Wifi
Wheelchair access
Room features
Air conditioning
Refrigerator in room
Family Rooms
Non-smoking rooms
Smoking rooms available
Good to know


Full view
42Car recommended
Grade: 42 out of 100
21Restaurantswithin 0.75 miles
0Attractionswithin 0.75 miles
11Room tips
Traveler rating
  • 4
  • 2
  • 5
  • 6
  • 30
Time of year
Traveler type
  • Filter
  • English
I stay in motels and hotels all over the world. I’ve stayed in many places in third world countries that were not so good. The Driftwood Inn shouldn’t even be open, it should be condemned. Missing window in bathroom, hair on the bed, wall outlets hanging out, missing lightbulbs
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If you are looking for an affordable no-frills, quiet, clean and comfortable place to get a good night’s sleep, you’ll be happy. What you get: a clean bed with a new and comfortable mattress, new carpeting, bathrooms that are renovated and clean, a mini fridge, microwave, TV,
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Came home with a case of bed bugs. Did not feel safe sleeping at night as there was no sliding lock on the door that opened to the outside. Room was dirty and toilet had wrong size seat on it. Bathtub was painted and the rest of the room had paint splatters all over.
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I stayed here the night before racing a half Ironman triathlon. My race schedule takes me to some pretty 'interesting' places off the well trodden path and I've spent the night in some motels and hotels that barely deserve the title. So truthfully I wasn't expecting much from
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Response from Jay D, Manager at Driftwood Inn
Responded Jan 8, 2018
Thank you for choosing our establishment for your stay while in Chestertown. We have done a major renovation to the motel from the past and have also upgraded our wifi infrastructure. We have updated our pictures online from the past and we are happy we exceeded your expectations! We hope to see you again during your future visits to Chestertown!
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Management is friendly, and you can tell they are upgrading and improving. Room was clean and housekeeping came daily. Plenty of parking. Town is very close and shopping center, including Acme for food in plaza right next door.
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Response from Jay D, Manager at Driftwood Inn
Responded Jan 8, 2018
Thank you for choosing our establishment during your stay in Chestertown. We have uploaded new pictures of our motel and are continuing more improvements. We hope to see you again soon! Thanks!
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Album Categories
All photosRoom & Suite
Photo provided by managementDriftwood Inn
King Bed Room
Photo provided by managementDriftwood Inn
Photo provided by managementDriftwood Inn
Double Bed Room
Photo provided by managementDriftwood Inn
Double Bed Room
Photo provided by managementDriftwood Inn
King Room
Hello, We do no have a pool at our establishment anymore as the demand did not suffice for the amount of pool users. There are numerous restaraunts within walkin distance from delis to an italian restaurant to pubs.
0 votes
"I had room 21 on the end. It was a little bigger, I think and in good condition."
"You're better off sleeping in your car at the strip mall up the road."
"It is a good place to sleep,shower and move on. Not for long term or business stays."
"Don't stay here. And if you do, bring a sleeping bag for on-top of the beds. And don't bring valuables. And really just stay away."
"Just stay away - comfort inn and holiday inn express nearby use them."
$63 - $144 (Based on Average Rates for a Standard Room)
United StatesMarylandChestertown
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