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Find hotels in Chestertown, MD from ￥8,907

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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, (861)
Dive into a tranquil retreat in Chestertown where guests praise the serene atmosphere and helpful staff. Enjoy morning workouts at the fitness center followed by refreshing swims in the seasonal outdoor pool. Rolling Road Park and the Historical Society of Kent County Maryland await nearby.
"Everything was well!"
United States
Ahmed
The price is ￥15,708
￥17,436 total
includes taxes & fees
Jan 25 - Jan 26, 2026
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)
Discover a luxurious escape with a private beach featuring comfortable chairs and umbrellas. This Chestertown lodge offers a 9-hole golf course, outdoor pool, and 3 bars/lounges. Enjoy free WiFi and parking while exploring nearby Pooles Island Light.
"Very nice rooms, "
United States
Stephania
The price is ￥15,438
￥17,651 total
includes taxes & fees
Dec 28 - Dec 29
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
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, (421)
Located near Rolling Road Park and Historical Society of Kent County Maryland, this quiet hotel offers free WiFi and parking. The helpful staff receives consistent praise from guests, while the 24-hour front desk ensures support throughout your stay.
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is ￥11,227
￥12,463 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Red Roof Inn & Suites Chestertown
Exterior
Holiday Inn Express & Suites Middletown by IHG

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, (651)
Located near Westown and Everett Theatre, this hotel offers complimentary breakfast, WiFi, and parking. Take a refreshing morning swim or workout anytime. Clean rooms provide comfort while the exceptionally helpful staff ensures a pleasant visit.
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is ￥14,053
￥15,599 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Holiday Inn Express & Suites Middletown by IHG
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (471)
Set near Belcamp Beach and Cedar Lane Regional Park, this hotel offers complimentary WiFi and parking. After a morning swim or fitness center workout, business travelers will appreciate the convenient location just 13 minutes from Aberdeen Station.
"Good room and service "
United States
Robert
The price is ￥12,943
￥14,497 total
includes taxes & fees
Dec 29 - Dec 30
Candlewood Suites Aberdeen-Bel Air by IHG
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, (325)
This Middletown hotel offers a refreshing indoor pool and free continental breakfast daily. Nearby attractions include Westown and Everett Theatre. Guests appreciate the helpful staff, and enjoy amenities like complimentary WiFi and 24-hour front desk service.
"Clean room, great staff, recommended. "
United States
Tom
The price is ￥16,842
￥18,695 total
includes taxes & fees
Dec 30 - Dec 31
Fairfield Inn & Suites by Marriott Middletown
Free daily self-serve breakfast
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1001)
This hotel near Dover Downs Casino offers an outdoor pool and fitness center for your relaxation. Complimentary breakfast, WiFi, and parking add value while Snowland attraction waits nearby for family adventures.
"Great stay"
United States
Edward
The price is ￥10,618
￥11,786 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Quality Inn Smyrna
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (338)
This business-friendly hotel in Aberdeen offers free breakfast and parking. Take a morning swim in the indoor pool or enjoy a workout anytime. Just minutes from Cal Ripken Museum and Ripken Stadium, with attentive staff ready to assist.
"Ty"
United States
Mary
The price is ￥11,139
￥12,475 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (866)
Unwind in this Middletown retreat featuring an indoor pool, hot tub, and fitness center. Just minutes from Everett Theatre and local attractions, the hotel offers convenient dining at BOB EVANS restaurant and a welcoming bar. Helpful staff ensures a comfortable experience.
"Amazing stay"
United States
Katiana
The price is ￥14,833
￥16,464 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hampton Inn Middletown
Lobby
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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, (1003)
Within a short drive of Aberdeen Station, this hotel offers a seasonal outdoor pool and convenient dining at the on-site restaurant. Clean rooms and attentive staff create a welcoming atmosphere, while free breakfast, WiFi, and parking enhance your stay near Belcamp Beach.
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is ￥12,350
￥13,832 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (606)
"very pet friendly!!"
United States
larry
The price is ￥15,319
￥17,157 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hampton Inn & Suites Baltimore/Aberdeen
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is ￥18,636
￥26,108 total
includes taxes & fees
Dec 28 - Dec 29
Kent Island Resort
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A

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, (1009)
Escape to a peaceful environment in Edgewood where quiet rooms and helpful staff await. Just minutes from CopperPlex and Emmorton Recreation Center, this hotel offers free WiFi, parking, and daily continental breakfast between 6-9 AM.
"Room was very nice. Staff is always very nice."
United States
Peggy
The price is ￥9,277
￥10,390 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn & Suites Bel Air I-95 Exit 77A
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, (562)
This serene Edgewood hotel offers a 24-hour fitness center with complimentary parking, WiFi, and continental breakfast. Located near dining options and Interstate 95, it's minutes from CopperPlex and Emmorton Recreation Center.
"This is my forth time at this hotel. Excellent service . Not staying for breakfast but usually very good"
United States
Carolyn
The price is ￥12,787
￥14,321 total
includes taxes & fees
Dec 27 - Dec 28
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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, (1000)
Step into a welcoming atmosphere where a seasonal outdoor pool awaits after a day of exploration. Located near restaurants and major roads, this hotel offers free breakfast, WiFi and parking. Fellow travelers praise the helpful staff and quiet environment.
"Nice place"
United States
Maria
The price is ￥13,918
￥15,588 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (95)
Free daily breakfast buffet and convenient parking make this a top choice. Guests praise the attentive staff while enjoying amenities like free WiFi. Located close to Cedar Lane Regional Park with easy access to Aberdeen Station, this hotel combines comfort and practicality.
"Spotless, very good "
United States
Efrain
The price is ￥16,997
￥19,035 total
includes taxes & fees
Dec 27 - Dec 28
TownePlace Suites by Marriott Edgewood Aberdeen
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (218)
Experience comfort at this Aberdeen hotel featuring a fitness center and indoor pool. Grab a bite at the coffee shop or unwind with a drink at the bar. Located near Ripken Stadium and Cal Ripken Museum, with free WiFi and parking for convenient exploration.
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
The price is ￥13,122
￥14,696 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Courtyard Aberdeen at Ripken Stadium
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (233)
Located near a train station, this Bel Air hotel offers an indoor pool for relaxation. The helpful staff ensures a pleasant stay, and with a restaurant, bar, and fitness center, travelers have all essentials for a comfortable visit near Belcamp Beach.
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
The price is ￥15,217
￥17,043 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Hilton Garden Inn Bel Air
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1000)
Enjoy a leisurely morning swim in the indoor pool and complimentary breakfast at this Edgewood gem. Business travelers appreciate the health club, free WiFi, and helpful staff, while nearby attractions like CopperPlex offer entertainment options.
"Room was great staff friendly"
United States
Melissa
The price is ￥13,043
￥14,607 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (1001)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Center.
"Nice place "
United States
Tucker T
The price is ￥13,009
￥14,440 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Best Western Kent Narrows Inn
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)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
See properties

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The chef was amazing"
Karla 1-night trip
Posted 3 days ago
Hilton Garden Inn 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 ￥7,953 per night from Dec 28 to Dec 29
￥7,953
￥8,907 total
Dec 28 - Dec 29
includes taxes & fees
5.6/10 (1,001 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 The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your trip. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best vacation rentals that Chestertown has to offer?
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Chestertown offers a balcony, a garden, and a barbecue grill 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 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, 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 39 hotels and other accommodations to choose from. Find out more about Chestertown.
What are the top places to visit 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. 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.

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