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Check prices for these dates

Next weekend
25 Jul - 27 Jul
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1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

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, (871)
"Great price, nice staff. "
The price is AED 268
AED 300 total
includes taxes & fees
21 Jul - 22 Jul
Days Inn by Wyndham Aberdeen
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (820)
"Staff is great & rooms always good "
The price is AED 215
AED 241 total
includes taxes & fees
27 Jul - 28 Jul
Super 8 by Wyndham Aberdeen 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, (376)
"My every need was meet and the staff was pleasant.."
The price is AED 312
AED 361 total
includes taxes & fees
21 Jul - 22 Jul
Super 8 by Wyndham Baltimore/Essex Area
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (488)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is AED 310
AED 353 total
includes taxes & fees
13 Aug - 14 Aug
Village Inn
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"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 AED 570
AED 633 total
includes taxes & fees
10 Aug - 11 Aug
Mariners Motel
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AED 233
AED 259 total
includes taxes & fees
27 Jul - 28 Jul
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
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
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
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
Super 8 by Wyndham Joppa
In-room safe, desk, free cribs/infant beds, rollaway beds

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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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The Inn was the perfect location for a visit to Annapolis-right in the heart of the downtown! Friendly staff and nice accommodations! I will definitely stay there again when I return to Annapolis. "
Mary 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

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 44 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 Aberdeen MD: Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi, and parking. Located 21.8 mi (35.1 km) from the heart of Chestertown. Village Inn: Central Chestertown is 25.6 mi (41.1 km) away. Free WiFi, free parking, and laundry facilities 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.