An aerial view of a town with a river, buildings, and surrounding greenery.

Find Chestertown motels from $66

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Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Chestertown motels

A row of motel rooms with stone walls and red doors.

1. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
$64 nightly
The price is $70
Sep 30 - Oct 1
Total with taxes and fees
Driftwood Inn
A spacious interior with a staircase, a chandelier, a stone wall, and a Day's Inn snack bar.

2. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (1,001 reviews)
"It was a restful stay."
United States
Luis
$81 nightly
The price is $91
Sep 30 - Oct 1
Total with taxes and fees
Days Inn by Wyndham Aberdeen
Private kitchen

3. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (525 reviews)
"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."
United States
Keith
$83 nightly
The price is $95
Sep 30 - Oct 1
Total with taxes and fees
Village Inn Annapolis MD
A Super 8 hotel with a prominent sign, a large building with multiple windows, and a well-lit entrance.

4. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (905 reviews)
"Good"
United States
Piyush
$59 nightly
The price is $66
Oct 8 - Oct 9
Total with taxes and fees
Super 8 by Wyndham Aberdeen MD
A multi-story motel with a brick facade, multiple windows, and a parking lot.

5. Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (514 reviews)
"Enjoyed my stay"
United States
Brittany
$87 nightly
The price is $100
Oct 4 - Oct 5
Total with taxes and fees
Super 8 by Wyndham Baltimore/Essex Area
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good
"Decent place to stay, good price."
Antonio 4-night trip
Posted 9 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,222
Accommodation
10 Motels
Lowest Price
$66
Highest Price
$100

Frequently asked questions

What are the best Chestertown motels, based on reviews?
Driftwood Inn stands out as an excellent choice for travelers seeking value and comfort in Chestertown, MD. With its family-friendly design and thoughtful amenities, this motel is particularly appealing for those with children. Guests love the cozy beds and competitive pricing, making it an inviting option for families or anyone on a budget. The daily housekeeping ensures a clean and straightforward stay, while the child-friendly window design adds an extra layer of safety for younger guests.
What is the nightly rate for a motel in Chestertown?
You can find a great deal from $66 on Chestertown motels with Expedia. Typically, prices are higher during popular times – like weekends and holidays – while staying midweek is often cheaper. To find the best nightly rates on Chestertown motels, try to be flexible with travel dates, and sort search results by price from low to high.
Is it better to stay in a Chestertown motel or hotel?
Motels and Hotels have different perks. When you stay at a motel, you're likely to find free parking and an outdoor pool. Staying overnight at a motel, can be handy when requiring easy road access. You'll often have access to your room from outside, and directly from the parking lot. Hotels generally have room access from inside the building. Motels are also often less expensive than hotels. The word "motel" was coined in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.

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