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4 Jan - 5 Jan
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5 Jan - 6 Jan
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9 Jan - 11 Jan
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16 Jan - 18 Jan

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Our top choices for Chestertown hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (863)
"Everything was well!"
United States
Ahmed
The price is NZ$188
includes taxes & fees
25 Jan - 26 Jan
Comfort Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (425)
"Clean and friendly staff. Good location."
United States
Robert
The price is NZ$139
includes taxes & fees
11 Jan - 12 Jan
Red Roof Inn & Suites Chestertown
Front of property – evening/night
Driftwood Inn

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is NZ$122
includes taxes & fees
25 Jan - 26 Jan
Driftwood Inn
Free continental breakfast
Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG
2.5 star property
Nottingham
9.6 out of 10, Exceptional, (1018)
"We always stay here when we travel to Baltimore. Rooms are always spotless and front desk staff accommodates late check out to make it convenient for their guests and their travel plans. "
United States
Melisa
The price is NZ$204
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express White Marsh by IHG
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870)
"Amazing stay"
United States
Katiana
The price is NZ$183
includes taxes & fees
13 Jan - 14 Jan
Hampton Inn Middletown
Reception
Relax Inn Smyrna

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
7.8 out of 10, Good, (93)
"The staff was great, the room was great. Everything I expected. I would definitely stay here again. It was close to the college. TV worked, and AC was running properly. Nothing bad to say about the rest inn. "
United States
maurice
The price is NZ$154
includes taxes & fees
5 Jan - 6 Jan
Relax Inn Smyrna
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (533)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"Clean and friendly staff"
United States
Lisa
The price is NZ$235
includes taxes & fees
11 Jan - 12 Jan
Hilton Garden Inn Kent Island Marina
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (327)
"Clean room, great staff, recommended. "
United States
Tom
The price is NZ$208
includes taxes & fees
11 Jan - 12 Jan
Fairfield Inn & Suites by Marriott Middletown
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1002)
"Nice place "
United States
Tucker T
The price is NZ$161
includes taxes & fees
11 Jan - 12 Jan
Best Western Kent Narrows Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (692)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is NZ$223
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh
2.5 star property
Nottingham
8.6 out of 10, Excellent, (1003)
"Great place to stay"
United States
brian
The price is NZ$203
includes taxes & fees
8 Jan - 9 Jan
Fairfield Inn & Suites by Marriott White Marsh
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Exterior
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (563)
"A solid place to stay in the area!"
United States
Donald
The price is NZ$161
includes taxes & fees
6 Jan - 7 Jan
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1015)
"Great stay as always"
United States
Linda
The price is NZ$158
includes taxes & fees
11 Jan - 12 Jan
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
7.8 out of 10, Good, (823)
"I love this property very quiet and it's convenient to the shopping center and if you want other food it's connected to an IHOP you don't have to go out in the elements "
United States
Shelia
The price is NZ$147
includes taxes & fees
18 Jan - 19 Jan
Comfort Inn & Suites Aberdeen near APG
Vending machine
Red Roof Inn Edgewood

Red Roof Inn Edgewood

Red Roof Inn Edgewood
2.0 star property
Edgewood
7.2 out of 10, Good, (848)
"Room was runned down,staff was excellent,amenities ok,"
United States
Alane
The price is NZ$129
includes taxes & fees
7 Jan - 8 Jan
Red Roof Inn Edgewood
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (433)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is NZ$344
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Lobby
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (304)
"Always consistent and great staff!"
United States
Linda
The price is NZ$212
includes taxes & fees
8 Jan - 9 Jan
Fairfield Inn & Suites by Marriott Aberdeen
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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Stay near popular Chestertown attractions

Washington College

4.1/5 (45 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
See properties

Historical Society of Kent County Maryland

Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
See properties

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

More cheap accommodation in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is NZ$99 per night from 5 Jan to 6 Jan
NZ$99
5 Jan - 6 Jan
includes taxes & fees
5.6/10 (999 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Comfort Inn & Suites Chestertown is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend Red Roof Inn & Suites Chestertown and Driftwood Inn as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best holiday rentals that Chestertown has to offer?
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Chestertown.
If I need to cancel my hotel reservation in Chestertown, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.
What's the best family accommodation in Chestertown?
Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What is the top LGBTQ-friendly hotel in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.
What's the best hotel to stay near the beach in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach . See more stays near the beach in Chestertown.
What are some accommodation options with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.
How is it to stay in Chestertown?
Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 39 hotels and other accommodation options to choose from. Find out more about Chestertown.
What should I see while I'm in Chestertown?
Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Chestertown Dog Park. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. Take a look at what more there is to see and do in Expedia's Chestertown guide.
What's the seasonal weather like in Chestertown?
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.

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