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Search Motels in Chestertown

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

Days Inn by Wyndham Aberdeen
2.0 star property
6.8 out of 10, (723)
"Brandi was very helpful and professional GIVE HER A RAISE SHE WAS THE 5 PLUS STAR I RATED TO A decent location "
The price is AED 248
AED 275 total
includes taxes & fees
9 Jun - 10 Jun
Days Inn by Wyndham Aberdeen
Super 8 by Wyndham Aberdeen MD
2.0 star property
6.8 out of 10, (692)
"It was clean and good for the price "
The price is AED 206
AED 229 total
includes taxes & fees
11 Jun - 12 Jun
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.0 out of 10, (301)
"Room was very clean and comfy. Staff was great. Location was great for an event at Rocky Point. One issue - and I've never complained about noise at a hotel in my life. But my room was the closet to the lobby desk. And for a long while around midnight - there was a lengthy conversation in the lobby - with one voice being a very loud male voice. I recommend a sign posted in the lobby asking people to keep conversations at a minimum volume late at night. One more thing - since I couldn't sleep...
The price is AED 323
AED 395 total
includes taxes & fees
6 Jun - 7 Jun
Super 8 by Wyndham Baltimore/Essex Area
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Village Inn
2.0 star property
6.2 out of 10, (436)
"It’s extremely affordable and for the price the room was basic and clean. Parking is directly in front of your room and there wasn’t much around the motel, so it feels safe. The room had a smell which we think was cleaning products that was a little strong."
The price is AED 354
AED 404 total
includes taxes & fees
10 Jun - 11 Jun
Village Inn
Driftwood Inn
2.0 star property
5.0 out of 10, (160)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is AED 233
AED 259 total
includes taxes & fees
9 Jun - 10 Jun
Driftwood Inn
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (85)
"Really cute property and rooms. The rooms are small but exceptionally clean and nicely decorated. Pretty grounds with a pool, fire pit, hammocks and yard games available. Easy walking distance to a few restaurants. Staff was very pleasant. "
The price is AED 612
AED 680 total
includes taxes & fees
10 Jun - 11 Jun
Mariners Motel
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
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
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
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
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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.

Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (5)
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is AED 2,310
AED 5,280 total
includes taxes & fees
7 Jun - 8 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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 43 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 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 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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