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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, (870 reviews)
  • cleanliness
    Peaceful waterfront stay with outdoor pool and fitness center near Kent County sights.
"Polite and kind hotel manager"
United States
Richard
The price is ₩146,117
₩162,190 total
includes taxes & fees
Mar 1 - Mar 2
Comfort 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)
  • cleanliness
    Private beach and 9-hole golf course steps from the seasonal pool.
"Very nice rooms, "
United States
Stephania
The price is ₩156,012
₩178,369 total
includes taxes & fees
Mar 1 - Mar 2
The Lodge at Great Oak Landing
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)
  • cleanliness
    Stay peacefully close to Chestertown attractions at this welcoming hotel.
"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 ₩104,009
₩115,450 total
includes taxes & fees
Feb 8 - Feb 9
Red Roof Inn & Suites Chestertown
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, (342 reviews)
  • cleanliness
    Comfortable stay near Westown with indoor pool and complimentary breakfast.
"Clean room, great staff, recommended. "
United States
Tom
The price is ₩139,978
₩155,375 total
includes taxes & fees
Feb 8 - Feb 9
Fairfield Inn & Suites by Marriott Middletown
Studio Suite, 1 King Bed with Sofa bed, Non Smoking | Free WiFi, bed sheets

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, (1,007 reviews)
  • cleanliness
    Convenient stay near Baltimore with free breakfast and relaxing amenities.
"Delicious breakfast and very spacious rooms. "
United States
Jen
The price is ₩99,386
₩111,318 total
includes taxes & fees
Feb 3 - Feb 4
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,004 reviews)
  • cleanliness
    Modern hotel close to Emmorton Recreation & Tennis Center with indoor pool.
"Great stay as always"
United States
Linda
The price is ₩117,269
₩131,341 total
includes taxes & fees
Feb 7 - Feb 8
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (660 reviews)
  • cleanliness
    Experience a convenient stay in Middletown with an indoor pool and 24-hour fitness center.
"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"
United States
Valerie
The price is ₩130,010
₩144,311 total
includes taxes & fees
Mar 1 - Mar 2
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, (618 reviews)
"Good customer service and the room was spotless!"
United States
George
The price is ₩140,960
₩157,874 total
includes taxes & fees
Feb 8 - Feb 9
Hampton Inn & Suites Baltimore/Aberdeen
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, (1,000 reviews)
  • cleanliness
    Enjoy a relaxing poolside retreat near Cedar Lane Park in a comfortable hotel setting.
"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 ₩116,374
₩130,338 total
includes taxes & fees
Mar 1 - Mar 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (869 reviews)
  • cleanliness
    Quiet hotel near Chesapeake Bay offers convenient access to local attractions.
"Nice staff and rooms"
United States
Walter
The price is ₩122,788
₩136,295 total
includes taxes & fees
Mar 2 - Mar 3
Quality Inn Grasonville near Kent Island
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, (242 reviews)
  • cleanliness
    Riverside comfort near train station with indoor pool and fitness center.
"Very friendly staff and easy check in."
United States
Kurt
The price is ₩140,960
₩157,874 total
includes taxes & fees
Feb 13 - Feb 14
Hilton Garden Inn Bel Air
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (132 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is ₩179,940
₩250,269 total
includes taxes & fees
Feb 3 - Feb 4
Kent Island Resort
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, (1,045 reviews)
  • cleanliness
    Serene Edgewood hotel near CopperPlex with free breakfast and ample parking.
"Decent place not loud quiet and out of the way."
United States
Tarrell
The price is ₩85,807
₩96,103 total
includes taxes & fees
Feb 8 - Feb 9
Quality Inn & Suites Bel Air I-95 Exit 77A
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (309 reviews)
  • cleanliness
    Relax in Aberdeen with easy access to Ripken Stadium and a refreshing indoor pool.
"Always consistent and great staff!"
United States
Linda
The price is ₩158,150
₩177,128 total
includes taxes & fees
Feb 5 - Feb 6
Fairfield Inn & Suites by Marriott 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, (1,002 reviews)
  • cleanliness
    Experience comfort and convenience at this Aberdeen hotel near Ripken Stadium.
"Room was great and staff excellent. "
United States
Robert
The price is ₩125,243
₩140,271 total
includes taxes & fees
Feb 7 - Feb 8
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (873 reviews)
  • cleanliness
    Enjoy a relaxing stay near Westown with free breakfast and parking at this hotel.
"Amazing stay"
United States
Katiana
The price is ₩137,407
₩152,522 total
includes taxes & fees
Feb 10 - Feb 11
Hampton Inn 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, (956 reviews)
  • cleanliness
    Serene waterfront retreat with peaceful grounds and convenient bike trail access.
"Lovely location"
United States
Cheryl
The price is ₩150,234
₩166,760 total
includes taxes & fees
Mar 2 - Mar 3
Holiday Inn Express Annapolis East-Kent Island by IHG
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)
  • cleanliness
    Waterside hotel with scenic sunset views and a refreshing indoor pool.
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is ₩120,505
₩133,761 total
includes taxes & fees
Feb 8 - Feb 9
Best Western Kent Narrows Inn
Exterior

Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
3.0 star property
Belcamp
8.4 out of 10, Very Good, (753 reviews)
  • cleanliness
    Convenient hotel with fitness center near Belcamp Beach and transit connections.
"Definitely was a great stay !"
United States
Shawn
The price is ₩118,454
₩132,670 total
includes taxes & fees
Feb 5 - Feb 6
Holiday Inn Belcamp - Aberdeen Area by IHG
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, (1,004 reviews)
  • cleanliness
    Enjoy a cozy retreat near Delaware's entertainment hubs with friendly service.
"Great stay"
United States
Edward
The price is ₩104,008
₩115,449 total
includes taxes & fees
Feb 8 - Feb 9
Quality Inn Smyrna
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.
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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 harbor.

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

Top Chestertown Hotel Reviews

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"The room layout was very good. Like it was done by someone who actually traveled a lot. Nice small kitchen. Lots of counter space. Several hooks in bathroom. Counter space in bathroom. "
Michael 2-night trip
Posted 19 hours ago
Home2 Suites by Hilton Baltimore/White Marsh

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is ₩66,305 per night from Feb 8 to Feb 9
₩66,305
₩74,250 total
Feb 8 - Feb 9
includes taxes & fees
5.6/10 (1,003 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Comfort Inn & Suites Chestertown is a favorite 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 trip. 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, most hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, 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.
Where can I learn more about changing or cancelling my trip to Chestertown?
For more details about rescheduling or cancelling your trip to Chestertown, click here.
What's the best hotel for families 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 kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.
What's the best LGBTQ-friendly accommodation 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 other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best pet-friendly hotel in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a fitness center for its human guests. Other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.
Where is the best hotel to stay near Washington College?
Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.
What about the best place to stay near Rolphs Wharf Marina?
One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.
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 accommodations with pools in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, and free WiFi. View all hotels with pools in Chestertown.
What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?
Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.
How is it to stay in Chestertown?
Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 38 hotels and other accommodations to choose from. Find out more about Chestertown.
What are the top places to visit in Chestertown?
Cultural venues include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. 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. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.