Chestertown Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Feb - 27 Feb
Tomorrow
27 Feb - 28 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

Filter by

Guest rating
Guest rating
Star rating

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, (879 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is €95
includes taxes & fees
8 Mar - 9 Mar
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)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is €75
includes taxes & fees
28 Feb - 1 Mar
Red Roof Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is €105
includes taxes & fees
23 Mar - 24 Mar
The Lodge at Great Oak Landing
Desk, laptop workspace, iron/ironing board, free WiFi

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (369 reviews)
"Staff was very courteous "
United States
Tina
The price is €104
includes taxes & fees
6 Mar - 7 Mar
SpringHill Suites by Marriott Edgewood/Aberdeen
Free daily continental breakfast

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, (574 reviews)
"A solid place to stay in the area!"
United States
Donald
The price is €87
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Lobby

Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
3.0 star property
Bel Air
8.8 out of 10, Excellent, (467 reviews)
"Yes we enjoyed it all staff was great felt like they really cared"
United States
Alex
The price is €93
includes taxes & fees
5 Mar - 6 Mar
Homewood Suites by Hilton Bel Air
Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (932 reviews)
"Clean rooms, great staff"
United States
Patricia
The price is €59
includes taxes & fees
1 Mar - 2 Mar
Days Inn by Wyndham Aberdeen
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is €88
includes taxes & fees
1 Mar - 2 Mar
Best Western Kent Narrows Inn
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (718 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is €103
includes taxes & fees
16 Mar - 17 Mar
Hyatt Place Kent Narrows & Marina
View from property

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.2 out of 10, Wonderful, (106 reviews)
"Clean room and attentive staff ."
United States
Stephen
The price is €125
includes taxes & fees
28 Feb - 1 Mar
TownePlace Suites by Marriott Edgewood Aberdeen
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (876 reviews)
"Nice staff and rooms"
United States
Walter
The price is €79
includes taxes & fees
8 Mar - 9 Mar
Quality Inn Grasonville near Kent Island
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, (1,003 reviews)
"We always enjoy our stay here when visiting our family as the facility is clean, comfortable and quiet. Only exception was on one of the days a fire alarm had gone off and scared us awake but it turned out to be a false alarm. "
United States
Cheryle
The price is €78
includes taxes & fees
23 Mar - 24 Mar
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Restaurant

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (226 reviews)
"Had a very pleasant check in with this hotel. Many restaurants are within a mile of the hotel. Very close to I-95. "
United States
Dennis
The price is €80
includes taxes & fees
15 Mar - 16 Mar
Courtyard Aberdeen at Ripken Stadium
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (350 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is €91
includes taxes & fees
15 Mar - 16 Mar
Fairfield Inn & Suites by Marriott Middletown
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (963 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is €89
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very good, (855 reviews)
"Room was nice area was good"
United States
Armond
The price is €70
includes taxes & fees
8 Mar - 9 Mar
Comfort Inn & Suites Aberdeen near APG
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, (245 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is €100
includes taxes & fees
8 Mar - 9 Mar
Hilton Garden Inn Bel Air
Deluxe Room | Interior detail

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
7.8 out of 10, Good, (93 reviews)
"Great location"
United States
Patrick
The price is €84
includes taxes & fees
1 Mar - 2 Mar
Relax Inn Smyrna
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,877 reviews)
"Great rooms, very clean, loved our stay "
United States
Matthew
Historic Inns of Annapolis
Basic Double or Twin Room

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.4 out of 10, Good, (10 reviews)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
The price is €47
includes taxes & fees
1 Mar - 2 Mar
Motel Edgewood
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

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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Very clean and stay was better than expected."
Daniel 1-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is €48 per night from 1 Mar to 2 Mar
€48
1 Mar - 2 Mar
includes taxes & fees
5.8/10 (1,000 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. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best holiday rentals that Chestertown has to offer?
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac: This holiday home rental outside of Chestertown is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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. The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. 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.

Explore a world of travel with Expedia