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Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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Our top choices for Rolling Road Park hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a sofa, a bed, a round table, and a TV mounted on the wall.
A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.
A reception desk with a flat-screen TV, a cash register, and a payment terminal. There are two pendant lights above the desk, and a large abstract painting on the wall.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
1.1 km from Rolling Road Park
United States
Amy
₩134,526
₩149,323 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A multi-story brick building with a covered entrance and a parking lot.
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.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
1 km from Rolling Road Park
United States
Kate
₩96,576
₩107,200 total
includes taxes & fees
Oct 13 - Oct 14
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A two-story building with a brick facade, large windows, and a sloped roof.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

3. Driftwood Inn

Driftwood Inn
0.7 km from Rolling Road Park
United States
Kathy
₩85,185
₩94,562 total
includes taxes & fees
Oct 7 - Oct 8
Driftwood Inn
A two-story house with a covered porch, a staircase, and a garden area.
A row of stationary bicycles with green frames and white seats, parked outdoors.
A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

4. Haven Point Inn and Gallery

Haven Point Inn and Gallery
19 km from Rolling Road Park
United States
Joe
₩179,136
₩198,842 total
includes taxes & fees
Nov 4 - Nov 5
Haven Point Inn and Gallery
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 campfire in a stone fire pit by a lakeside at sunset.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.1 km from Rolling Road Park
United States
Sandra
₩144,882
₩165,643 total
includes taxes & fees
Oct 8 - Oct 9
The Lodge at Great Oak Landing
A boat deck with a white bench and a view of a calm lake and distant trees.
A sunflower field with a white barn and a large house in the background.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

6. Inn at Huntingfield Creek

Inn at Huntingfield Creek
19.1 km from Rolling Road Park
United States
Christine
₩215,002
₩238,653 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek
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Compare popular hotels close to Rolling Road Park

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
Comfort Inn & Suites Chestertown
8.6
Excellent
989 reviews
View
A hotel room with a sofa, two beds, a painting, and a lamp.
Red Roof Inn & Suites Chestertown
7.2
Good
508 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
5.4
183 reviews
View
A two-story house with a covered porch, a staircase, and a garden area.
Haven Point Inn and Gallery
9.6
Exceptional
16 reviews
View
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
The Lodge at Great Oak Landing
8.0
Very good
116 reviews
View

Top Rolling Road Park Hotel Reviews

Other attractions near Rolling Road Park

Washington College

8.6/10 (87 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.
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Larrabee Arts Center

Enjoy an outing to Larrabee Arts Center during your stay in Chestertown. Experience the area's festivals and art scene.
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Chestertown Farmers Market

You can browse for the perfect souvenirs at Chestertown Farmers Market during your stay in Chestertown. Experience the area's festivals and art scene.
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Historical Society of Kent County Maryland

7.4/10 (6 reviews)
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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River Arts Chestertown

7.4/10 (6 reviews)
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
You can get tickets for a performance 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 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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Sumner Hall

You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene.
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Frequently asked questions

What's the area like around Rolling Road Park?
Rolling Road Park is located in Chestertown. Travelers like the surrounding area for its university setting. If you're looking for a convenient place to stay, check out the 15 hotels and other accommodations you'll find within a mile.
What's the best place to stay near Rolling Road Park?
The Lodge at Great Oak Landing is one of the top choices for your stay based on our traveler data, and this lodge offers a golf course and 2 restaurants. You'll find it 8.1 mi (13.1 km) from Rolling Road Park. Other good options in the area include Quality Inn Grasonville near Kent Island and Hilton Garden Inn Kent Island Marina.
How many hotels should I expect to find close to Rolling Road Park?
Expedia has 15 hotels and other accommodations within a mile from Rolling Road Park.
If I need to cancel the hotel reservation for my stay near Rolling Road Park, will I receive a refund?
Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to view top deals close to Rolling Road Park.
Where can I learn more about changing or cancelling my trip in the area near Rolling Road Park?
To find more details about rescheduling or cancelling your stay near Rolling Road Park, head over to our customer service page.
What can I see and do near Rolling Road Park?
You can wander around Chestertown Dog Park, Urieville Park, or Urieville Lake Fish Management Area if you want a dose of fresh air. You'll have countless hours of family fun at Larrabee Arts Center, Garfield Center for the Arts at the Prince Theater, and Schooner Sultana. Washington College and Historical Society of Kent County Maryland are both worth a visit while you're checking out the area.