Find hotels in Chestertown, MD from ฿1,846

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Our top choices for Chestertown hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (896 reviews)
"Best place to stay always "
United States
Robert
The price is ฿3,691
฿4,097 total
includes taxes & fees
26 Apr - 27 Apr
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (434 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 ฿2,278
฿2,528 total
includes taxes & fees
26 Apr - 27 Apr
Red Roof Inn & Suites Chestertown

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 ฿3,460
฿3,956 total
includes taxes & fees
13 Apr - 14 Apr
The Lodge at Great Oak Landing

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh
3.0 star property
Nottingham
8.6 out of 10, Excellent, (1,006 reviews)
"Room clean and breakfast has a variety of food items. "
United States
William
The price is ฿3,241
฿3,743 total
includes taxes & fees
26 Apr - 27 Apr
Fairfield Inn & Suites by Marriott White Marsh

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, (1,075 reviews)
"It was a comfortable stay. "
United States
Fayaz
The price is ฿1,797
฿2,013 total
includes taxes & fees
12 Apr - 13 Apr
Quality Inn & Suites Bel Air I-95 Exit 77A

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, (1,009 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is ฿2,832
฿3,172 total
includes taxes & fees
19 Apr - 20 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,011 reviews)
"Clean room, nice staff and great breakfast "
United States
Curtis
The price is ฿2,732
฿3,060 total
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (635 reviews)
"Friendly and clean, great staff!"
United States
Sharon
The price is ฿3,021
฿3,384 total
includes taxes & fees
4 May - 5 May
Hampton Inn & Suites Baltimore/Aberdeen

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is ฿4,966
฿5,512 total
includes taxes & fees
22 Apr - 23 Apr
Haven Point Inn and Gallery

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)
"Very nice place to stay. They offer a good breakfast buffet Variety.Beds very comfortable they offer daily room service just all around good stay would recommend."
United States
Donald
The price is ฿3,117
฿3,491 total
includes taxes & fees
20 Apr - 21 Apr
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (832 reviews)
"I enjoyed my stay and everything was perfect "
United States
Castro
The price is ฿4,008
฿4,629 total
includes taxes & fees
16 Apr - 17 Apr
SpringHill Suites Baltimore White Marsh/Middle River

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very good, (878 reviews)
"Would stay again! Very great place "
United States
Mindy
The price is ฿2,588
฿2,899 total
includes taxes & fees
6 May - 7 May
Comfort Inn & Suites Aberdeen near APG

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (943 reviews)
"Very good option, friendly staff and good price "
United States
Jose
The price is ฿2,076
฿2,325 total
includes taxes & fees
12 Apr - 13 Apr
Days Inn by Wyndham Aberdeen

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center
2.5 star property
Medford
7.8 out of 10, Good, (1,003 reviews)
"Parking was absolutely good I felt safe while staying there "
United States
Emely
The price is ฿3,421
฿4,020 total
includes taxes & fees
3 May - 4 May
Best Western Plus Hotel & Conference Center

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, (585 reviews)
"Clean room, friendly staff, good food, excellent!"
United States
Dwayne
The price is ฿2,979
฿3,337 total
includes taxes & fees
11 May - 12 May
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is ฿2,595
฿2,880 total
includes taxes & fees
20 Apr - 21 Apr
Quality Inn Smyrna

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is ฿3,182
฿3,532 total
includes taxes & fees
22 Apr - 23 Apr
Best Western Kent Narrows Inn

Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
3.0 star property
Bel Air
8.8 out of 10, Excellent, (484 reviews)
"Our dog was welcomed and staff was very attentive "
United States
MARK
The price is ฿3,390
฿3,797 total
includes taxes & fees
19 Apr - 20 Apr
Homewood Suites by Hilton Bel Air

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie
2.5 star property
Glen Burnie
8.2 out of 10, Very good, (1,001 reviews)
"Nice clean rooms and staff. Good location"
United States
sherry
The price is ฿3,126
฿3,564 total
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn Baltimore/Glen Burnie

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD
3.0 star property
Rossville
7.2 out of 10, Good, (1,004 reviews)
"The room was nice and clean and the staff was nice and very helpful "
United States
carla
The price is ฿2,912
฿3,364 total
includes taxes & fees
3 May - 4 May
Country Inn & Suites by Radisson, Baltimore North, MD
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

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.

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

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveller data, Comfort Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free breakfast and free parking. Other good options for your trip to the area are Historic Inns of Annapolis and Hampton Inn Baltimore/Glen Burnie. See all available top hotels, or 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 43 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 Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. 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.