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Oct 15 - Oct 16
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Oct 16 - Oct 17
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Oct 16 - Oct 18
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Oct 23 - Oct 25

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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 Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
1.1 km from Rolling Road Park
United States
Amy
CA $139
CA $154 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A living room with a fireplace, a television, and a stone accent 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
1 km from Rolling Road Park
United States
Kate
CA $102
CA $114 total
includes taxes & fees
Nov 4 - Nov 5
Red Roof Inn & Suites Chestertown
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 two-story building with a brick facade, large windows, and a sloped roof.
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
CA $90
CA $100 total
includes taxes & fees
Oct 17 - Oct 18
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.
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.
A sunflower field with a white barn and a large house in the background.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
19.1 km from Rolling Road Park
United States
Christine
CA $228
CA $253 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek
A two-story house with a covered porch, a staircase, and a garden area.
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 garden with a lawn and a table with chairs under a canopy.
A row of stationary bicycles with green frames and white seats, parked outdoors.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
19 km from Rolling Road Park
United States
Joe
CA $190
CA $211 total
includes taxes & fees
Oct 20 - Oct 21
Haven Point Inn and Gallery
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
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.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.1 km from Rolling Road Park
United States
Sandra
CA $154
CA $176 total
includes taxes & fees
Oct 20 - Oct 21
The Lodge at Great Oak Landing
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Compare popular hotels close to Rolling Road Park

Property
Star rating
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
510 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
5.4
183 reviews
View
A boat deck with a white bench and a view of a calm lake and distant trees.
Inn at Huntingfield Creek
10.0
Exceptional
74 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

Top Rolling Road Park Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Just like always a nice quiet place to stay"
Thomas 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

8/10 Good
"The staff answered any and all questions, were friendly and helpful. The room was spacious and clean. Breakfast was available buffet style and the coffee was hot. There were plenty of parking spaces, so parking was not a problem. There were other food options right across the street."
Phyllis 4-night trip
Posted 2 hours ago
SpringHill Suites Baltimore White Marsh/Middle River
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"Clean"
Denee 1-night trip
Posted 21 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"The breakfast is good, rooms are clean, and the staff is always friendly and helpful."
David 9-night trip
Posted 2 days ago
Home2 Suites by Hilton Baltimore/White Marsh
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good
"Nice location. Good staff. Pet friendly +++"
Laura Lee 1-night trip
Posted 2 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent
"Good"
Cruz 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."
Craig 1-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"We stay here frequently. The best hotel in a great location."
Bryan 1-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

10/10 Excellent
"The place is clean and well maintained - older but still in great shape. It was nice and quiet and is close to a lot. The staff was incredibly friendly from check-in to check-out. They made sure I enjoyed my stay, the last night as a single woman and our first night as a married couple."
Jennifer 2-night trip
Posted 3 days ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

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.
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.