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Search Motels in Chestertown

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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, (789)
"Clean and quiet. Bed sheets and blanket can be in better condition. Reception staff was not friendly. Seemed annoyed she had to be there. It served its one night purpose. "
The price is HK$443
HK$496 total
includes taxes & fees
17 Dec - 18 Dec
Days Inn by Wyndham Aberdeen
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (467)
"Clean and cozy"
The price is HK$584
HK$665 total
includes taxes & fees
24 Nov - 25 Nov
Village Inn
Super 8 by Wyndham Aberdeen MD
Exterior

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (755)
"Met expectations for a good low priced accommodation."
The price is HK$390
HK$437 total
includes taxes & fees
4 Dec - 5 Dec
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, (331)
"Mold on the bathroom ceiling. No electricity in the bathroom for the hair dryer. I should have paid less for my stay. However, the price was the lowest of the owner hotels Woman at the desk during the evening is fantastic. The woman at the desk during the morning is a sweetheart also. "
The price is HK$662
HK$811 total
includes taxes & fees
24 Nov - 25 Nov
Super 8 by Wyndham Baltimore/Essex Area
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 HK$494
HK$549 total
includes taxes & fees
24 Nov - 25 Nov
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 HK$1,119
HK$1,242 total
includes taxes & fees
24 Nov - 25 Nov
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
Games 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
Hillside Motel
Lobby lounge

Hillside Motel

2.0 star property
4.8 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
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
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

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Outdoor pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.
Beautiful view of the beach with palm trees

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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 43 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. Super 8 by Wyndham Aberdeen MD: A 24-hour front desk 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. Days Inn by Wyndham Aberdeen: Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi and self-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 centre along with freebies such as WiFi, self-parking and a cruise ship terminal shuttle are available during your stay. Hilltop Motel: 20.5 mi (33.1 km) from the heart of Chestertown. Enjoy access to the snack bar/deli, and freebies including WiFi and self-parking.
What can I do in Chestertown?
Some outdoorsy places nearby include Wilmer Park, Betterton Beach and Miami Beach. 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 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.