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Find Chestertown motels from $65

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Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Motels in Chestertown

Days Inn by Wyndham Aberdeen
Two spacious beds with white linens flank dark headboards, offering a serene view of a bridge and water.

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (874)
"Great price, nice staff. "
$66 nightly
The price is $74
Sep 1 - Sep 2
Total includes taxes and fees
Days Inn by Wyndham Aberdeen
Super 8 by Wyndham Aberdeen MD
Simple, functional design with a central entrance and well-maintained surroundings.

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (827)
"Everything is good for a business trip, simply sleep"
$58 nightly
The price is $65
Sep 1 - Sep 2
Total includes taxes and fees
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Baltimore/Essex Area
Stay at this two-story motel with a brick facade, featuring air conditioning units and a parking lot with designated spaces.

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
5.4 out of 10, (379)
"My every need was meet and the staff was pleasant.."
$101 nightly
The price is $117
Aug 11 - Aug 12
Total includes taxes and fees
Super 8 by Wyndham Baltimore/Essex Area
Village Inn
Relax in a spacious room with a large bed, nightstand, and comfortable armchair.

Village Inn

2.0 star property
6.2 out of 10, (490)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
$81 nightly
The price is $93
Aug 10 - Aug 11
Total includes taxes and fees
Village Inn
Mariners Motel
Docked in the marina, a sleek yacht awaits your arrival.

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
$155 nightly
The price is $172
Aug 10 - Aug 11
Total includes taxes and fees
Mariners Motel
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
$64 nightly
The price is $70
Aug 6 - Aug 7
Total includes taxes and fees
Driftwood Inn
White Marsh Motel
Enjoy a formal dining experience in our restaurant with a warm atmosphere, elegant decor, and modern amenities.

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
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
Regal Inn & Suites
Combined shower/tub, free toiletries, towels, soap

Regal Inn & Suites

2.0 star property
3.4 out of 10, (397)
Regal Inn & Suites
Hillside Motel
Porch

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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Top Chestertown Hotel Reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Check in took a few extra minutes since there was only one staff member and several checking in. "
Wendy 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh

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 $65 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.