Default HTG hotel image

Top Hotels Near Rolling Road Park in Chestertown from AU$100

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Filter by

Property class

Guest rating

Our top choices for Rolling Road Park hotels

A multi-story brick building with a covered entrance and a parking lot.
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, a sofa, a desk, and a painting on the wall.

1. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
1 km from Rolling Road Park
United States
Linda
AU$114
includes taxes & fees
19 Oct - 20 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
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.

2. Driftwood Inn

Driftwood Inn
0.7 km from Rolling Road Park
United States
Kathy
AU$100
includes taxes & fees
29 Sept - 30 Sept
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
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 marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.1 km from Rolling Road Park
United States
Jane
AU$176
includes taxes & fees
30 Sept - 1 Oct
The Lodge at Great Oak Landing
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 buffet with various food items including fruits, pastries, and salads.
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.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
19.1 km from Rolling Road Park
United States
Christine
AU$285
includes taxes & fees
19 Oct - 20 Oct
Inn at Huntingfield Creek
View all properties

Top Rolling Road Park Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"The hotel was very clean,easy to find and the staff was polite."
Leslie 1-night trip
Posted 4 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Good stay. I wish I could have used the spa. It was closed on tuesdays. I also wish they could have provided free breakfast for the price that they charge per room"
Rathna 1-night trip
Posted 11 hours ago
The Inn at Chesapeake Bay Beach Club
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

8/10 Good
"Everyone was pleasant but the hotel was older and fairly expensive for the quality and look of the hotel. It was a motel at one point."
Beth 2-night trip
Posted 11 hours ago
Best Western Kent Narrows Inn
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

10/10 Excellent
"A+"
Leah 4-night trip
Posted 14 hours ago
Quality Inn Grasonville near Kent Island
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Pet friendly. Full breakfast. Desk was accommodating for a ground floor room for my dog. Room was clean and comfortable."
Wayne 1-night trip
Posted 2 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"room was clean, and the breakfast was as expected. The only bad thing was that treadmill in the gym was out of service, which I found disappointing."
Steven 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

10/10 Excellent
"The staff at the reception was courteous. The room was clean and the treatment was excellent."
Jose 1-night trip
Posted 3 days ago
SpringHill Suites Baltimore White Marsh/Middle River
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

8/10 Good
"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."
Jane 1-night trip
Posted 5 days ago
The Lodge at Great Oak Landing

Other attractions near Rolling Road Park

Washington College

8.6/10 (87 reviews)
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
See properties

Larrabee Arts Center

Enjoy an outing to Larrabee Arts Center during your stay in Chestertown. 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.
See properties

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

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.
See properties

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.
See properties

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.
See properties

Frequently asked questions

What's the area like around Rolling Road Park?
Rolling Road Park is located in Chestertown. Travellers like the surrounding area for its university setting. If you're looking for a convenient place to stay, take a look at the 15 hotels and other accommodation options you'll find within a mile.
What's the best hotel to stay near Rolling Road Park?
The Lodge at Great Oak Landing is one of the top choices for your stay based on our traveller 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 choices 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 accommodation options 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, the majority of hotel bookings are fully refundable if you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Enter dates in and click on "Search", then you can use the "fully refundable" filter to view the best deals available near 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 out exploring.