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Chestertown Hotel Guide - Roundtop Park hotels in Chestertown, United States of America.

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Roundtop Park hotels

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a desk, two chairs, a flat-screen TV, and a painting on the wall.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
4.4 km from Roundtop Park
United States
Roberta
€97
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A multi-story brick building with a covered entrance and a parking lot.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
4.3 km from Roundtop Park
United States
Kate
€71
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
16.4 km from Roundtop Park
United States
Steve allen
€110
includes taxes & fees
8 Nov - 9 Nov
The Lodge at Great Oak Landing
A row of motel rooms with stone walls and red doors.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
A two-story building with a brick facade, large windows, and a sloped roof.

4. Driftwood Inn

Driftwood Inn
4.1 km from Roundtop Park
United States
Kathy
€63
includes taxes & fees
25 Oct - 26 Oct
Driftwood Inn
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Hotels recommended for families near Roundtop Park

A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A multi-story brick building with a covered entrance and a parking lot.

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
€71
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a desk, two chairs, a flat-screen TV, and a painting on the wall.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
€97
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.
A modern kitchen with white cabinets, a central island, and pendant lighting.
A modern kitchen with a large island, white cabinetry, and a view of the city.
A laundry room with two front-loading washing machines, a drying rack, and a small cabinet above the machines.

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
€317
includes taxes & fees
25 Oct - 26 Oct
Newly restored apartment in the heart of Chestertown
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A swimming pool with a curved edge, surrounded by a brick patio and a hedge.
A closet with a wooden floor, a white door, and a blue bag on top.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
€146
includes taxes & fees
26 Oct - 27 Oct
First Floor Studio Apartment in Historic Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
€110
includes taxes & fees
8 Nov - 9 Nov
The Lodge at Great Oak Landing
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.
A garden with a statue, various shrubs, and a flower bed.
A grassy outdoor seating area with Adirondack chairs and a small table, surrounded by trees.
A marina with boats docked, a building with a white facade, and a restaurant with outdoor seating.

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
€263
includes taxes & fees
22 Nov - 23 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A boat deck with a white bench and a view of a calm lake and distant trees.
A buffet with various food items including fruits, pastries, and salads.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.
A sunflower field with a white barn and a large house in the background.

Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
€139
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
€82
includes taxes & fees
15 Nov - 16 Nov
Quality Inn Grasonville near Kent Island

Top Roundtop Park Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"The rooms very clean and accommodating. Definitely will stay there again when we travel through."
Frank 1-night trip
Posted 7 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

8/10 Good
"Small room for 2 persons only one trash can Pillows were lumpy bumpy Mattress not great No iron./table Clean room had fridge microwave Breakfast is modest Good location Convenient"
andrew 1-night trip
Posted 9 hours ago
Quality Inn Grasonville near Kent Island
240' Private Beachfront @Kent Island Love Point - Great for Families

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent
"Clean, quiet property with well equipped kitchen and various inside/outside areas for groups to relax, Great view of sunrise from beach or house. Best to bring own games, bikes, outdoor activities as opposed to relying on what is there."
Kevin S. 2-night trip
Posted 1 day ago
240' Private Beachfront @Kent Island Love Point - Great for Families
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good
"Good location, easy access to local restaurants. The staff is friendly and helpful. I would recommend staying here"
Terry Kyungho 2-night trip
Posted 1 day ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"
Beth 1-night trip
Posted 2 days ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Property was quiet and clean and close to town."
Roberta 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

10/10 Excellent
"Cool spot by a marina. House felt clean and good beds."
Nathaniel Richard 4-night trip
Posted 5 days ago
The Lodge at Great Oak Landing
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

8/10 Good
"Solid for the type of accommodations. Would be nice if breakfast was served past 9"
William 1-night trip
Posted 5 days ago
Fairfield Inn & Suites by Marriott Middletown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

8/10 Good
"The place was a little better than average, I'd stay here again. The room smelled musty as if it used to be a smoking room, but not completely unbearable. The desk help was not friendly but not rude either...kind of robotic. Easy parking, roomy room. Decent shower."
Bill 1-night trip
Posted 6 days ago
Red Roof Inn & Suites Chestertown

Other attractions near Roundtop Park

Kings Town Park

Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
See properties

Rolling Road Park

Rolling Road Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
See properties

Historical Society of Kent County Maryland

7.4/10 (6 reviews)
You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Chestertown Historic District

Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.
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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
You can make plans for a show at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Chestertown Farmers Market

You can find the perfect gifts to bring home at Chestertown Farmers Market during your trip to Chestertown. Experience the area's festivals and art scene.
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Sumner Hall

You can spend time exploring the galleries in Sumner Hall during your travels in Chestertown. Experience the area's festivals and art scene.
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River Arts Chestertown

7.4/10 (6 reviews)
Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.
See properties

Frequently asked questions

What's the area like around Roundtop Park?
Roundtop Park is located in Chestertown. Travellers like the surrounding area for its university setting. You'll find 33 hotels and other accommodations within a few miles for a convenient home base.
What's the best hotel to stay near Roundtop Park?
Red Roof Inn & Suites Chestertown is one of the top choices for your stay based on our traveller data, and this hotel offers free parking and free WiFi. It's located 2.7 mi (4.3 km) from Roundtop Park. Another good choice is Comfort Inn & Suites Chestertown, located 2.7 mi (4.4 km) away.
How many hotels are there close to Roundtop Park?
Expedia has 33 hotels and other accommodation options a few miles from Roundtop Park.
If I need to cancel the hotel reservation for my stay near Roundtop Park, will I receive a refund?
Yes, the majority of hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of your booking. Enter dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals near Roundtop Park.
What can I see and do near Roundtop Park?
Spend some time exploring the the natural beauty of Chestertown Dog Park, Urieville Park and Urieville Lake Fish Management Area. You'll have countless hours of family fun at Garfield Center for the Arts at the Prince Theater, Schooner Sultana and Larrabee Arts Center. Historical Society of Kent County Maryland and Chestertown Historic District are some sights worth a visit in the area.