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Search Motels in Chestertown

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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

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

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, (820)
"Cozy hotel "
The price is AED 248
AED 277 total
includes taxes & fees
31 Mar - 1 Apr
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, (768)
"Excellent service and cozy room "
The price is AED 206
AED 231 total
includes taxes & fees
10 Mar - 11 Mar
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
5.2 out of 10, (344)
"Comfortable. Very kind and welcoming staff. All the comforts needed for a restful sleep on a business trip. "
The price is AED 294
AED 339 total
includes taxes & fees
5 Mar - 6 Mar
Super 8 by Wyndham Baltimore/Essex Area
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (472)
"I love this place! All the rooms are spacious. The entire staff is great! "
The price is AED 305
AED 348 total
includes taxes & fees
5 Mar - 6 Mar
Village Inn
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.0 out of 10, (167)
"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
5 Mar - 6 Mar
Driftwood Inn
Mariners Motel
Outdoor pool

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 AED 528
AED 586 total
includes taxes & fees
5 Mar - 6 Mar
Mariners Motel
White Marsh Motel
Exterior detail

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
Game room

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
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
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
Hillside Motel
Lobby lounge

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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Other property types in Chestertown

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is AED 360
AED 579 total
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

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.
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (256)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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 41 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. Super 8 by Wyndham Baltimore/Essex Area: Central Chestertown is 21.8 mi (35 km) away. A business center along with freebies like WiFi, parking, and a cruise ship terminal shuttle 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: Kings Town Park, Rolling Road Park, and Chestertown Dog 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: Rolphs Wharf Marina, Historical Society of Kent County Maryland, 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.