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Oct 10 - Oct 12
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Featured Motels in Chestertown

Days Inn by Wyndham Aberdeen
In-room safe, desk, soundproofing, iron/ironing board

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (893)
"Was a great place to stay for 8 hours"
The price is P4,147
P4,644 total
includes taxes & fees
Oct 12 - Oct 13
Days Inn by Wyndham Aberdeen
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
7.0 out of 10, Good, (849)
"Parking was easy. Bed was super comfy. "
The price is P3,512
P3,934 total
includes taxes & fees
Oct 8 - Oct 9
Super 8 by Wyndham Aberdeen MD
Village Inn Annapolis MD
Coffee service

Village Inn Annapolis MD

2.0 star property
6.2 out of 10, (502)
"The room was very nice, clean and quiet. Great location"
The price is P4,831
P5,507 total
includes taxes & fees
Nov 2 - Nov 3
Village Inn Annapolis MD
Super 8 by Wyndham Baltimore/Essex Area
Exterior

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.4 out of 10, (393)
"Just a nice quiet cool place clean rooms and the bed is away from the door lol"
The price is P4,249
P4,907 total
includes taxes & fees
Oct 5 - Oct 6
Super 8 by Wyndham Baltimore/Essex Area
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is P8,359
P9,279 total
includes taxes & fees
Nov 2 - Nov 3
Mariners Motel
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
The price is P3,693
P4,099 total
includes taxes & fees
Nov 2 - Nov 3
Driftwood Inn
White Marsh Motel
Restaurant

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
Combined shower/tub, free toiletries, towels, soap

Regal Inn & Suites

2.0 star property
3.4 out of 10, (397)
Regal Inn & Suites
Rodeway Inn
Lobby

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
Porch

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
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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Top Chestertown Hotel Reviews

Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

10/10 Excellent
"Didn’t have made to order breakfast. They’re many shops nearby. Room was clean and fresh. "
Renee 3-night trip
Posted 1 day ago
Courtyard by Marriott Baltimore Downtown/McHenry Row

Find out more about Chestertown

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,898
Accommodation
11 Motels
Lowest Price
P3,934
Highest Price
P9,279

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 42 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. Village Inn: Enjoy access to the laundry facilities, and freebies including WiFi and parking. Located 25.6 mi (41.1 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. Super 8 by Wyndham Baltimore/Essex Area: 21.8 mi (35 km) from the heart of Chestertown. Enjoy the in-room free WiFi, and freebies including breakfast, parking, and a cruise ship terminal shuttle.
What can I do in Chestertown?
These are some of the parks and outdoorsy places: Chestertown Dog Park, Urieville Park, and Urieville Lake Fish Management Area. 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.

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