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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

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, (888)
"Good nice area "
The price is NZ$123
includes taxes & fees
21 Sept - 22 Sept
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, (844)
"Owner and MGMT really cleaning up the place."
The price is NZ$109
includes taxes & fees
2 Oct - 3 Oct
Super 8 by Wyndham Aberdeen MD
Village Inn
View from room

Village Inn

2.0 star property
6.2 out of 10, (498)
"The room was very nice, clean and quiet. Great location"
The price is NZ$173
includes taxes & fees
25 Sept - 26 Sept
Village Inn
Super 8 by Wyndham Baltimore/Essex Area
Exterior

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.4 out of 10, (391)
"Room was nice shady characters outside though"
The price is NZ$186
includes taxes & fees
28 Sept - 29 Sept
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 NZ$293
includes taxes & fees
22 Sept - 23 Sept
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 NZ$120
includes taxes & fees
14 Oct - 15 Oct
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/bathtub, 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Stayed for one night; room was nice, easy to access, and located near numerous local attractions. "
Clifton 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

Find out more about Chestertown

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,878
Accommodation
11 Motels
Lowest Price
NZ$109
Highest Price
NZ$293

Frequently asked questions

What can I expect from a motel trip to Chestertown?
If you can't find 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. Just use our search tools to filter by nightly room rate or cost-saving amenities such as free breakfast and free airport transport.
What's it like to stay in a motel?
At most motels, you're likely to find a free parking spot and an outdoor pool. When you stay at a motel, you'll often have access to your room from an outside corridor overlooking the car park. Motels began in the 1920s as a place to stay for the weary traveller driving along America's major roadways.
What are the best motels in Chestertown?
Here are some of our customers' top motels to book in the larger area. Driftwood Inn: Enjoy access to the 24-hour front desk, and freebies including WiFi and self-parking. Days Inn by Wyndham Aberdeen: A seasonal outdoor pool along with freebies such as breakfast, WiFi and self-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 self-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 such as breakfast, WiFi and self-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, self-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 road trip, 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What are my options for getting around Chestertown while staying in a motel?
We've gathered some information about getting around 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 city centre. Otherwise, you can search for flights to 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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