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Find Chestertown motels from $61

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

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
Oct 23 - Oct 24
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
7.2 out of 10, Good, (1,000 reviews)
"The value for price was exceptional. Friendly and helpful staff."
United States
Daniel
$68 nightly
The price is $76
Nov 15 - Nov 16
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, (528 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
Oct 25 - Oct 26
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, (913 reviews)
"It was clean and comfortable. Breakfast had yummy waffles and yogurt. We had a good night."
United States
Jeannine
$54 nightly
The price is $61
Nov 10 - Nov 11
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, (522 reviews)
"Clean room"
United States
Michael
$89 nightly
The price is $103
Nov 16 - Nov 17
Total with taxes and fees
Super 8 by Wyndham Baltimore/Essex Area
A restaurant with wooden beams, stone walls, and a fireplace. Tables are set with red tablecloths and chairs.

6. White Marsh Motel

White Marsh Motel
2.0 star property
White Marsh
6.6 out of 10, (27 reviews)
"Starting with the checking service was friendly and accommodating "
United States
William
$80 nightly
The price is $92
Nov 9 - Nov 10
Total with taxes and fees
White Marsh 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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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Best in room dining"
Edgar 4-night trip
Posted 12 hours ago
Pendry Baltimore

Find out more about Chestertown

Chestertown Motels information

Number of reviews
711
Accommodation
10 Motels
Lowest Price
$61
Highest Price
$103

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 $61 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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