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

Find Chestertown motels from $68

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19
In one month
Jul 31 - Aug 2
In two months
Aug 28 - Aug 30

Our top choices for Chestertown motels

Front of property - evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
$64 nightly
The price is $70
Jul 1 - Jul 2
Total with taxes and fees
Driftwood Inn
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
"The room was very nice, clean and quiet. Great location"
United States
William
$83 nightly
The price is $95
Jul 6 - Jul 7
Total with taxes and fees
Village Inn Annapolis MD
Restaurant

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
Jul 13 - Jul 14
Total with taxes and fees
White Marsh Motel
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (883 reviews)
"Room was dirty, housekeeping ignored the do not disturb sign and barged in when trying to get dressed and would not leave. Roaches in room."
United States
Farrah
$60 nightly
The price is $68
Jul 28 - Jul 29
Total with taxes and fees
Super 8 by Wyndham Aberdeen MD
Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (988 reviews)
"It's better than Red Roof but definitely spend the money for better if with the Family"
United States
Christopher
$71 nightly
The price is $80
Jul 5 - Jul 6
Total with taxes and fees
Days Inn by Wyndham Aberdeen
Exterior

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (480 reviews)
"SPOTLESSLY CLEAN ROOM BIG WORKING TV, EASY CHECK-IN & CHECK-OUT Premises Could Be Better Kept A bit Noisy"
United States
Jared
$90 nightly
The price is $104
Jul 7 - Jul 8
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"The hotel was very clean. The breakfast was ok. The items were not checked frequently for being hot and replenished. The staff was very helpful when asked for assistance even at breakfast. I would definitely stay again. We plan to come back in September. It was a convenient location to get to the Harbor area. The parking was convenient and free."
Florence 3-night trip
Posted 8 hours ago
Hampton Inn Baltimore Bayview Campus

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,528
Accommodation
10 Motels
Lowest Price
$68
Highest Price
$104

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 $68 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.

Explore a world of travel with Expedia