Chestertown
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Top 10 Hotels in Chestertown

Image for Stunning Home on a 25-acre Private Woodland Estate
8221 Broad Neck Rd, Chestertown, MD
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4.9/5Exceptional! (18 reviews)
Beautiful, immaculately clean property

"This house really is the perfect getaway. The house is very smartly designed and decorated. The grounds are stunning as are the views of them. The pictures really don’t do it justice. This is the perfect place to unwind. And this is by far the cleanest house we’ve ever rented. We couldn’t recommend ..."…"

Reviewed on 5 Dec 2018

Stunning Home on a 25-acre Private Woodland Estate
Image for Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town
4.7/5Exceptional! (7 reviews)
Great for a family

"We had a great time. The house was very clean and comfortable. The grandkids had a lot of room inside and out. Already want to return. Thank you for a great vacation spot."…"

Reviewed on 7 Aug 2018

Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town
Image for Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
5/5Exceptional! (21 reviews)
Great Family Spot!

"Another great vacation for our family at this wonderful home on the Chester River. An inviting and relaxing atmosphere; so much so that we have returned for another year to this clean, well-appointed and terrific location."…"

Reviewed on 15 Jul 2019

Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
Image for Chester River Waterfront, Magnificent Views, Dock, Beach
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4.6/5Exceptional! (14 reviews)
Peaceful gem on the Chester river

"This was a perfect place to recuperate from a busy summer. I told the owner she may need to have me surgically removed from the dock when our stay was over. It was quiet and relaxing, yet never strayed into boring, Chestertown and the vicinity has plenty to see and do- there are a lot of cute shops ..."…"

Reviewed on 10 Sep 2018

Chester River Waterfront, Magnificent Views, Dock, Beach
Image for Contemporary Waterfront House With Private Dock & Kayaks!
10751 Kasota Rd, Chestertown, Maryland
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5/5Exceptional! (11 reviews)
Relaxing few days away from the city

"My wife and I had a quiet and relaxing time here last week. We were surprised at the variety of birds we saw - about 20 we could identify at the bird feeder here and at the Eastern Neck wildlife sanctuary. We kayaked slowly around Worton Creek to appreciate the natural environment, and took in the ..."…"

Reviewed on 22 Apr 2019

Contemporary Waterfront House With Private Dock & Kayaks!
Image for Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD
£177/night
22 Sep-23 Sep
4.7/5Exceptional! (16 reviews)

"If you are looking for a peaceful, relaxing and restful vacation, this is the place. Breakfasts are phenomenal!!! Holly is the exceptional host. Rooms are nice, clean and taken care of. I loved the history of the house. Great local restaurants. We had an amazing time!!!"…"

Reviewed on 30 Aug 2019

Great Oak Manor
Image for Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
Free cancellationReserve now, pay when you stay
£75/night
17 Sep-18 Sep
2.1/5 (104 reviews)

"Rooms were clean and site has great internet. This isn’t a large chain so don’t expect a continental breakfast and free coffee. It was a place to stay the night and it was perfect for that."…"

Reviewed on 24 Jun 2019

Driftwood Inn
Image for Inn at Mitchell House
3 out of 5
8796 Maryland Pkwy, Chestertown, MD
£133/night
22 Sep-23 Sep
4.9/5Exceptional! (12 reviews)

"Lovely historic house – very congenial innkeepers."…"

Reviewed on 22 Aug 2019

Inn at Mitchell House
Image for John L Stam House
3 out of 5
114 Washington Ave, Chestertown, MD
Free cancellationReserve now, pay when you stay
£169/night
17 Sep-18 Sep
4.9/5Exceptional! (19 reviews)

"This review comes with a note of caution. It is a lovingly restored old Victorian house, operated as a B&B. If you like that sort of thing, you will absolutely love it. The people who own it are great (friendly, accommodating and interesting, as well as good cooks!), as is the "breakfast" part of ..."…"

Reviewed on 19 Apr 2019

John L Stam House
Image for Best Western Plus Hotel & Conference Center
3 out of 5
5625 O'Donnell Street, Baltimore, MD
Free cancellationReserve now, pay when you stay
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3.6/5Good! (1,743 reviews)

"That there was a eating place. The property was hidden in such a way to hide your real surrounding."…"

Reviewed on 9 Sep 2019

Best Western Plus Hotel & Conference Center
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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 11 hotels and other accommodation options in Chestertown
  • The closest major airport is in Baltimore, MD (MTN-Martin State), 19.5 mi (31.3 km) from the city centre
  • 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 holiday, you'll find 11 hotels and other lodging options available to select from in Chestertown. Below are highly ranked ones based on our user reviews:

  • Holiday Inn Express Hotel & Suites Chestertown - With a stay at this 2.5-star hotel, guests can enjoy access to free breakfast and free parking, along with free WiFi. It's a favourite with Expedia travellers for its convenient parking and proximity to shopping.
  • Driftwood Inn - Our customers like the overall value and WiFi at this motel. With a stay at this 2-star motel, guests can enjoy access to free parking and a 24-hour front desk, along with free WiFi.

A top sight outside the city is Chesapeake Bay Bridge, located 21.4 mi (34.5 km) from the centre of the city.

Dressing for Chestertown

  • Between January and March, you can expect the daytime average to be around 15°C and the night-time average to be -4°C
  • From April to June, temperatures average about 30°C during the day and 4°C at night
  • July to September averages 30°C during the day and 12°C at night
  • Between October and December, the average temperature is 23°C during the day and -2°C at night
  • Chestertown gets about 36 millimetres of rain per year
  • Hottest months are usually July and August with an average temperature of 29°C, while the coldest months are January and February with an average of -2°C

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