Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Keith Mox on trover

Find Hotels in Chestertown, MD

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Chestertown hotels and places to stay

Quality Suites
2.5 out of 5
160 Scheeler Rd, Chestertown, MD
Get Rates
2.01 mi from city center
4/5Very Good! (106 reviews)
Great Stay

"The room was nice and clean. I was surprised by the size of the unit. I had enough room to move around. The staff was great, especially the ones working the breakfast."…"

Reviewed on Jul 28, 2016

Quality Suites
Hampton Inn Baltimore/White Marsh
2.5 out of 5
8225 Town Center Drive, Baltimore, MD
Free CancellationReserve now, pay when you stay
The price is $93 per night
22.72 mi from city center
4.2/5Very Good! (632 reviews)

"The only thing I can comment on was that there was no fan in the bathroom. I told the clerk when we checked out so that someone was advised. Other than that we had a great short stay"…"

Reviewed on May 25, 2020

Hampton Inn Baltimore/White Marsh
Home2 Suites by Hilton Baltimore/White Marsh
2.5 out of 5
10465 Philadelphia Road, White Marsh, MD
The price is $103 per night
21.87 mi from city center
4.2/5Excellent! (843 reviews)

"It advertised a jacuzzi and there wasnt one. The pool was extremely dirty, looked like it hadnt been cleaned in a long time.....this was extremely disappointing because i only booked this hotel for the pool and the jacuzzi. I couldve stayed downtown baltimore for the same or lower rate if i wasnt ..."…"

Reviewed on Mar 8, 2020

Home2 Suites by Hilton Baltimore/White Marsh
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
Free CancellationReserve now, pay when you stay
The price is $70 per night
1.84 mi from city center
2.2/5 (128 reviews)

"Convenient for Rock Hall triathlon event. Quiet (apart from triathletes talking outside). Room was clean and bed comfortable. Room had a microwave and bathroom was in good order."…"

Reviewed on Sep 29, 2019

Driftwood Inn
Inn at Mitchell House
3 out of 5
8796 Maryland Pkwy, Chestertown, MD
The price is $150 per night
7.39 mi from city center
4.8/5Exceptional! (19 reviews)
Wonderful and relaxing stay

"Lovely place, gracious owners, beautiful and spacious room, and fantastic breakfasts. I definitely want to go back! A particularly delightful place if you are a history buff, or into wildlife, as the national wildlife refuge is nearby."…"

Reviewed on Jan 12, 2020

Inn at Mitchell House
John L Stam House
3 out of 5
114 Washington Ave, Chestertown, MD
The price is $190 per night
1.6 mi from city center
4.9/5Exceptional! (23 reviews)

"T"…"

Reviewed on Nov 3, 2019

John L Stam House
Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD
The price is $159 per night
7.2 mi from city center
4.7/5Exceptional! (22 reviews)

"Great, friendly staff; building and grounds were excellently-maintained, room was comfy."…"

Reviewed on Jan 1, 2020

Great Oak Manor
Contemporary Waterfront House With Private Dock & Kayaks!
Get Rates
5.85 mi from city center
5/5Exceptional! (23 reviews)
Beautiful spot

"Lovely setting and wonderful house"…"

Reviewed on Oct 17, 2019

Contemporary Waterfront House With Private Dock & Kayaks!
Chester River Waterfront, Magnificent Views, Dock, Beach
Get Rates
3.1 mi from city center
4.8/5Exceptional! (43 reviews)
Bringing back memories!

"Loved our stay! The house was great, the views were great. Wish we had more time to be there. Had a wonderful time reminiscing of when I was a kid and coming down to Rock Hall area to my grandparents summer shack for many years on the Davis Creek. Tried looking for it but obviously not there anymore. ..."…"

Reviewed on Sep 24, 2019

Chester River Waterfront, Magnificent Views, Dock, Beach
Stunning Home on 25-acre Woodland Estate W/pool, Hot Tub&sauna. 5 BR, Sleeps10
4.9/5Exceptional! (55 reviews)
Fantastic getaway

"My friends and I had SUCH a fun getaway at Highfield Manor. Both house and grounds are gorgeous. Would absolutely stay again."…"

Reviewed on May 26, 2020

Stunning Home on 25-acre Woodland Estate W/pool, Hot Tub&sauna. 5 BR, Sleeps10
Can't find the place you want?
See all available properties in Chestertown
View all properties
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.

Visiting Chestertown

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art.

  • There are 9 hotels and other accommodations in Chestertown
  • The closest major airport is in Baltimore, MD (MTN-Martin State), 19.5 mi (31.4 km) from the city center
  • The next closest is in Easton, MD (ESN-Easton - Newnam), 27.3 mi (43.9 km) away

Sightseeing and Staying in Chestertown

The city's cultural venues include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. The university setting is a highlight of the city and Washington College is worth a campus tour. A couple of additional sights to add to your agenda are Wilmer Park and Rolphs Wharf Marina.

As you plan your vacation, you'll find 9 hotels and other lodging options available to select from in Chestertown. Below are highly ranked ones based on our user reviews:

  • John L Stam House - With a stay at this 3-star bed & breakfast, guests can enjoy access to free breakfast and free parking, along with free WiFi. It's a favorite with Expedia travelers for its breakfast and proximity to shopping.
  • Holiday Inn Express Hotel & Suites Chestertown - Our customers like the breakfast and quiet location at this hotel. With a stay at this 2.5-star hotel, guests can enjoy access to free breakfast and an indoor pool, along with free WiFi.
  • Quality Suites - This 2.5-star hotel features free breakfast, an indoor pool, and free WiFi.

Dressing for Chestertown

  • Between January and March, you can expect the daytime average to be around 58°F and the nighttime average to be 25°F
  • From April to June, temperatures average about 85°F during the day and 39°F at night
  • July through September averages 87°F during the day and 53°F at night
  • In October-December, the average temperature is 73°F during the day and 28°F at night
  • Chestertown gets about 1.42 inches of rain per year
  • Hottest months are usually July and August with an average temperature of 85°F, while the coldest months are January and February with an average of 28°F

Frequently asked questions

Where is the best place for a stay in Chestertown?
Great Oak Manor is a favorite property for Expedia customers. This 3.5-star B&B offers a private beach and free breakfast. Reviews from our site also recommend Holiday Inn Express Hotel & Suites Chestertown and Driftwood Inn as top options for your trip.
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. Plug in your dates, click on “Search”, then filter by “free cancellation” to review the best deals available 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 place to stay on a budget in Chestertown?
Based on reviews, Holiday Inn Express Hotel & Suites Chestertown is a popular 2.5-star hotel for our travelers looking for an economical choice, and features free buffet breakfast and free WiFi. Another top choice for your budget-friendly stay is Driftwood Inn.
What's the best hotel for families in Chestertown?
Driftwood Inn is a property with free parking and free WiFi, and it’s a top choice on Expedia for families. Holiday Inn Express Hotel & Suites Chestertown is another good choice for your kid-friendly vacation.
What's the best accommodation for a romantic vacation to Chestertown?
Great Oak Manor is a favorite 3.5-star B&B for couples, and features premium bedding and bathrobes. Another choice for your romantic getaway is Inn at Mitchell House.
What's the best pet-friendly hotel in Chestertown?
Great Oak Manor is a top B&B for people traveling with their pets, and offers a private beach and a fitness center for its human guests. Other good options to stay with your pet include Holiday Inn Express Hotel & Suites Chestertown and Driftwood Inn.
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 WiFi and free parking. Other good choices within a short distance include Holiday Inn Express Hotel & Suites Chestertown and John L Stam House.
What about the best place to stay near Rolphs Wharf Marina?
One of the top choices for your stay is Holiday Inn Express Hotel & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free WiFi. John L Stam House and Driftwood Inn are two other good choices within 5 miles.
What's the best hotel to stay near the beach in Chestertown?
Great Oak Manor is a top hotel for a beach vacation, and features free buffet breakfast and free WiFi. Other good choices to stay near the beach include Inn at Mitchell House and Great Oak Manor. Head to Earle Landing or Betterton Beach for some quality time by the water.
What's the best place to stay in Chestertown to absorb the local history?
Based on our travel expertise, Chester River Waterfront, Magnificent Views, Dock, Beach is a top historic vacation home bookable on our site and it features in-room kitchens. If you’re interested in local history, another option for your visit is Quality Suites.
What are some accommodations with pools in Chestertown?
Quality Suites is a top hotel with an indoor pool, free buffet breakfast, and free WiFi.

Recent reviews of Chestertown hotels

More trip options