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Check prices for these dates

Tonight
16 Jan - 17 Jan
Tomorrow
17 Jan - 18 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

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Our top choices for Chestertown hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (866 reviews)
"Everything was well!"
United States
Ahmed
The price is AU$166
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 reviews)
"Clean and friendly staff. Good location."
United States
Robert
The price is AU$119
includes taxes & fees
22 Jan - 23 Jan
Red Roof Inn & Suites Chestertown
Free daily continental breakfast

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

Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1,029 reviews)
"Decent place not loud quiet and out of the way."
United States
Tarrell
The price is AU$87
includes taxes & fees
25 Jan - 26 Jan
Quality Inn & Suites Bel Air I-95 Exit 77A
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (333 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is AU$168
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Middletown
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,003 reviews)
"Great stay as always"
United States
Linda
The price is AU$136
includes taxes & fees
22 Jan - 23 Jan
Hampton Inn & Suites Edgewood/Aberdeen-South
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,001 reviews)
"Great stay"
United States
Edward
The price is AU$117
includes taxes & fees
15 Feb - 16 Feb
Quality Inn Smyrna
Exterior

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (656 reviews)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is AU$152
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express & Suites Middletown by IHG
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (613 reviews)
"Everything looks great. Staff is very nice."
United States
David
The price is AU$141
includes taxes & fees
23 Jan - 24 Jan
Hampton Inn & Suites Baltimore/Aberdeen
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,001 reviews)
"Room was great and staff excellent. "
United States
Robert
The price is AU$142
includes taxes & fees
30 Jan - 31 Jan
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
United States
Jerry
The price is AU$248
includes taxes & fees
19 Jan - 20 Jan
Kent Island Resort
Reception

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (635 reviews)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is AU$145
includes taxes & fees
29 Jan - 30 Jan
Hilton Garden Inn Aberdeen
Indoor pool

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
2.5 star property
Edgewood
7.2 out of 10, Good, (1,000 reviews)
"Room was great for the price, friendly staff"
United States
Gary
The price is AU$92
includes taxes & fees
23 Jan - 24 Jan
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Bar (on property)

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (240 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is AU$163
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Bel Air
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
7.8 out of 10, Good, (829 reviews)
"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 AU$126
includes taxes & fees
30 Jan - 31 Jan
Comfort Inn & Suites Aberdeen near APG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870 reviews)
"Amazing stay"
United States
Katiana
The price is AU$158
includes taxes & fees
27 Jan - 28 Jan
Hampton Inn Middletown
Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is AU$147
includes taxes & fees
19 Jan - 20 Jan
Quality Inn Grasonville near Kent Island
Terrace/patio

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (432 reviews)
"Claudia at the front desk was awesome!! Clean room amd great location. Only downside was the loud traffic you could hear from the road in the room."
United States
Steven
The price is AU$175
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn Express Aberdeen by IHG
Lobby

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,007 reviews)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is AU$137
includes taxes & fees
11 Feb - 12 Feb
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Studio Suite, 1 King Bed with Sofa bed, Non Smoking

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very good, (1,002 reviews)
"Delicious breakfast and very spacious rooms. "
United States
Jen
The price is AU$112
includes taxes & fees
20 Jan - 21 Jan
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Standard Room, 2 Queen Beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (971 reviews)
"There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!"
United States
Carleen Lyden
The price is AU$89
includes taxes & fees
25 Jan - 26 Jan
Super 8 by Wyndham Havre De Grace Aberdeen 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.
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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

Wilmer Park

Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.
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

Recent Reviews in Chestertown

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Clean room, staff was very friendly and kept in touch throughout stay, to see if I needed anything. Highly recommended staying here"
raymond 2-night trip
Posted 4 days ago
Historic Inns of Annapolis

More cheap accommodation in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is AU$85 per night from 18 Jan to 19 Jan
AU$85
18 Jan - 19 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?
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of Chestertown is located on the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. 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 40 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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