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Search Motels in Chestertown

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Check prices for these dates

Compare 12 Motels in Chestertown with updated reviews, rates, and availability.

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (824)
"My stay was average for hotels in this same price range. Quiet and comfortable and the location was convenient to restaurants and shopping. "
The price is SAR 233
SAR 261 total
includes taxes & fees
23 Mar - 24 Mar
Days Inn by Wyndham Aberdeen

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.2 out of 10, (348)
"Always a welcoming staff. I feel safe here, and if there is anything I need, I know I will get help."
The price is SAR 278
SAR 321 total
includes taxes & fees
23 Mar - 24 Mar
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (774)
"Good stay"
The price is SAR 204
SAR 229 total
includes taxes & fees
2 Apr - 3 Apr
Super 8 by Wyndham Aberdeen MD

Village Inn

2.0 star property
6.2 out of 10, (473)
"The road leading to the hotel was trashy and homely."
The price is SAR 311
SAR 355 total
includes taxes & fees
21 Mar - 22 Mar
Village Inn

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is SAR 539
SAR 598 total
includes taxes & fees
27 Mar - 28 Mar
Mariners Motel

Driftwood Inn

2.0 star property
5.0 out of 10, (168)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is SAR 238
SAR 264 total
includes taxes & fees
29 Mar - 30 Mar
Driftwood Inn

White Marsh Motel

2.0 star property
6.6 out of 10, (27)
"Starting with the checking service was friendly and accommodating "
White Marsh Motel

Regal Inn & Suites

2.0 star property
3.4 out of 10, (397)
"They was rude i paid for a hot tub room the hot tub didn't work and the tv was broke they wouldn't give us another room i will never go back"
Regal Inn & Suites

Rodeway Inn

2.5 star property
6.4 out of 10, (237)
"Never had to post a security deposit ($75) before to rent a room. "
Rodeway Inn

Hillside Motel

2.0 star property
5.0 out of 10, (45)
"I never had a chance to stay because the office closed at 9 pm and NO ONE would answer the phone. In fact, someone picked up the phone and hung up on me. What hotel doesnt have a person on site at all times?!! I spoke with a gentleman at the liquor store and he said he heard of this problem every weekend. If you're going to close at 9 make it in BOLD PRINT."
Hillside Motel

Super 8 by Wyndham Joppa

2.5 star property
7.2 out of 10, Good, (252)
"Entire hotel was run down and not very clean. In fact it closed down while I was staying there. Hope they return my money for the night they kicked me out."
Super 8 by Wyndham Joppa
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.
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Other property types in Chestertown

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.

Frequently asked questions

What can I expect from a motel trip to Chestertown?
If you’re having difficulty finding a motel in Chestertown, consider some of the motels we suggest around the area or let us help you find something similar from over 43 hotels and other lodging options. Simply filter using our search tools by nightly room rate or cost-effective amenities such as free parking and free breakfast.
What's it like to stay in a motel?
At most motels, you’re likely to find an outdoor pool and a free parking spot. When you stay at a motel, you’ll often have access to your room from an outside corridor overlooking the parking lot. Motels began in the 1920s as a convenient place to stay for the weary traveler taking a road trip along America’s major roadways.
What are the best motels in Chestertown?
Here you’ll find some of our customers’ favorite motels to choose from in the larger area. Driftwood Inn: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Days Inn by Wyndham Aberdeen: A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking are available during your stay. Central Chestertown is 21.8 mi (35.1 km) away. Super 8 by Wyndham Baltimore/Essex Area: Enjoy access to the business center, and freebies including WiFi, parking, and a cruise ship terminal shuttle. Located 21.8 mi (35 km) from the heart of Chestertown. Super 8 by Wyndham Aberdeen MD: Central Chestertown is 21.8 mi (35.1 km) away. A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Village Inn: 25.6 mi (41.1 km) from the heart of Chestertown. Enjoy access to the laundry facilities, and freebies including WiFi and parking.
What can I do in Chestertown?
These are some of the parks and outdoorsy places: Urieville Lake Fish Management Area, Chestertown Dog Park, and Urieville Park. You’ll find these family-friendly attractions in the area: Crumpton Auction and Hazel Miner Monument. During your trip, here are some other places to visit: Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Garfield Center for the Arts at the Prince Theater.
What's the seasonal weather like in Chestertown?
Weather can make or break a roadtrip, so we’ve gathered some data about year-round temperatures in Chestertown to help you plan yours. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What are my options for getting around Chestertown when staying in a motel?
We’ve gathered some information about local transportation options in Chestertown to help you navigate your stay: Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the heart of the city. Otherwise, look for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you’d like to explore around the area, you may want to rent a car for your trip.