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Chestertown Hotels

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Check Chestertown hotel prices

Tonight
7 Nov - 8 Nov
Tomorrow night
8 Nov - 9 Nov
This weekend
8 Nov - 10 Nov
Next weekend
15 Nov - 17 Nov

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Top 10 trending Chestertown hotels

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing
3.5 star property
7.8 out of 10, Good, (44)
"Generally okay, Clean but property could use some upgrade"
The price is €104
includes taxes & fees
12 Nov - 13 Nov
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (723)
"Very clean and comfortable home away from home, and breakfast in the morning, too. Perfect place to stay to enjoy the Sultana Downrigging Festival, just a short drive away. And, Chestertown is a beautiful and friendly town, too!"
The price is €110
includes taxes & fees
4 Dec - 5 Dec
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (316)
"Room was ok, needed a little maintenance and TLC but was clean. Pool was closed indefinitely, and only 1 ice machine for the whole hotel. Doesn't appear owners are putting much $ into the place to keep it up."
The price is €82
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is €66
includes taxes & fees
11 Nov - 12 Nov
Driftwood Inn
Inn at Huntingfield Creek
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (47)
"Wonderful! Quiet and relaxing anniversary! Pool was great, dock is beautiful, room was clean, comfortable and spacious. Water bottles and cookies are such a nice touch. Breakfast was delicious. Amazing property and genuine hosts. Thank you"
The price is €199
includes taxes & fees
20 Nov - 21 Nov
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is €149
includes taxes & fees
10 Nov - 11 Nov
Mariners Motel
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is €146
includes taxes & fees
13 Nov - 14 Nov
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Exterior detail
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is €257
includes taxes & fees
8 Nov - 9 Nov
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Miscellaneous
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (17)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is €298
includes taxes & fees
10 Nov - 11 Nov
Waterfront Retreat with Private Dock and Beach
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (2)
"Thank you - towels hanging bathroom. Outside trash can was full when we got there. We took our trash with us. thank you - MBVK"
Bayside Cottage steps from Rock Hall Harbor
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (4)
"A great place to chill out and enjoy what Rock Hall has to offer. It’s always great to come back to my childhood town. Rick is a great host and takes really good care of the property! We will be back."
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Beach towels
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
9.8 out of 10, Exceptional, (60)
"Great place near the marina. Kitchen was well equipped for cooking our own meals. Nice recent updates to the bathroom and kitchen. Covered porch out back is also quite nice. We enjoyed our stay and would gladly return to this house!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Beach nearby, sun-loungers, beach towels
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
River Cottage, Chestertown
Fridge, microwave, oven, stovetop
River Cottage, Chestertown
2.0 star property
River Cottage, Chestertown
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (37)
"Love this place. It was perfect for us. Rooms are spacious. "
Serene Waterfront Cottage with dock and gorgeous views.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Fridge, microwave, oven, stovetop
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (63)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (30)
"We had my daughter's wedding at this beautiful villa. The views were absolutely amazing! The house is very spacious and accommodated our family. The sunsets were spectacular. Everyone enjoyed the pool, hot tub, and all the other activities this house had to offer"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Marina
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
10.0 out of 10, Exceptional, (13)
"We booked this home for the Waterman’s Triathlon Weekend. My wife was racing and I like to have a location close to the event so we don’t have to worry about driving/parking/commuting the morning of and this location was EXACTLY what we were looking for! This home was clean, spacious and homey! We had plenty of room for both of us to work remotely for a full day, great lounging living room and the garage access was a great perk as it gave us space to store all of my wife’s triathlon gear for...
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
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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Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favourite 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 stay. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. See all 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 accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels 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's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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 fitness centre and laundry facilities 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 located on the beach . Great Oak Manor is another good option to stay near the beach. See more stays near the beach in Chestertown.

What's the best hotel in Chestertown to learn about local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also, notable landmarks to visit include Historical Society of Kent County Maryland. See more options for historical stays 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, a private beach and 3 bars/lounges. View all hotels with pools in Chestertown.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre. See all spa hotels 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 Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Wilmer Park. 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.