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Find properties with these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
Next weekend
May 17 - May 19

Browse Select Chestertown Motels

Lobby
Days Inn by Wyndham Aberdeen
2.0 star property
6.8 out of 10, (722)
"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 £62
includes taxes & fees
12 May - 13 May
Days Inn by Wyndham Aberdeen
Exterior
Super 8 by Wyndham Aberdeen MD
2.0 star property
6.8 out of 10, (680)
"It was very nice and relaxing and close to all the restaurants. "
The price is £49
includes taxes & fees
22 May - 23 May
Super 8 by Wyndham Aberdeen MD
Exterior
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.0 out of 10, (296)
"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 £86
includes taxes & fees
27 May - 28 May
Super 8 by Wyndham Baltimore/Essex Area
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Lobby sitting area
Hilltop Motel
2.0 star property
4.8 out of 10, (714)
"The girls are very friendly and always ready to help you I really felt at home here "
The price is £53
includes taxes & fees
12 May - 13 May
Hilltop Motel
TV
Village Inn
2.0 star property
6.2 out of 10, (432)
"I have stayed here multiple times and have always enjoyed it"
The price is £87
includes taxes & fees
19 May - 20 May
Village Inn
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"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 £56
includes taxes & fees
20 May - 21 May
Driftwood Inn
Outdoor pool
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 £148
includes taxes & fees
12 May - 13 May
Mariners Motel
Exterior detail
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
Games room
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
Lobby lounge
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
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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

Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (50)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is £1,162
includes taxes & fees
16 May - 17 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Beach nearby, sun-loungers
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.

Chestertown Motels information

Number of reviews
3,553
Accommodation
11 Motels
Lowest Price
£49
Highest Price
£148

Frequently asked questions

What can I expect from a motel trip to Chestertown?
If you can’t find 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. Just use our search tools to filter by nightly room rate or cost-saving amenities such as free breakfast and free airport transport.
What's it like to stay in a motel?
At most motels, you’re likely to find a free parking spot and an outdoor pool. When you stay at a motel, you’ll often have access to your room from an outside corridor overlooking the car park. Motels began in the 1920s as a place to stay for the weary traveller driving along America’s major roadways.
What are the best motels in Chestertown?
Here are some of our customers’ top motels to book in the larger area. Driftwood Inn: Enjoy access to the 24-hour front desk, and freebies including WiFi and self-parking. Super 8 by Wyndham Aberdeen MD: A 24-hour front desk along with freebies such as breakfast, WiFi and self-parking are available during your stay. Central Chestertown is 21.8 mi (35.1 km) away. Days Inn by Wyndham Aberdeen: Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi and self-parking. Located 21.8 mi (35.1 km) from the heart of Chestertown. Super 8 by Wyndham Baltimore/Essex Area: Central Chestertown is 21.8 mi (35 km) away. A business centre along with freebies such as WiFi, self-parking and a cruise ship terminal shuttle are available during your stay. Hilltop Motel: 20.5 mi (33.1 km) from the heart of Chestertown. Enjoy access to the snack bar/deli, and freebies including WiFi and self-parking.
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 road trip, 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What are my options for getting around Chestertown while staying in a motel?
We’ve gathered some information about getting around 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 city centre. Otherwise, you can search for flights to 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.

Chestertown Hotel Reviews
Expedia verified reviews

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

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

5/5 Excellent
"Amazing hotel people that work there very friendly very clean safe "
A verified traveller stayed at Quality Inn & Suites Bel Air I-95 Exit 77A
Posted 1 day ago
Quality Inn & Suites Bel Air I-95 Exit 77A