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

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Check prices for these dates

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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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 spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
1.1 km from Rolling Road Park
United States
Amy
€97
includes taxes & fees
8 Nov - 9 Nov
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 living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
1 km from Rolling Road Park
United States
Kate
€71
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 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 living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
0.7 km from Rolling Road Park
United States
Kathy
€63
includes taxes & fees
13 Oct - 14 Oct
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.
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 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.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
19.1 km from Rolling Road Park
United States
Christine
€159
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
A two-story house with a covered porch, a staircase, and a garden area.
A garden with a lawn and a table with chairs under a canopy.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
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.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
19 km from Rolling Road Park
United States
Joe
€132
includes taxes & fees
13 Oct - 14 Oct
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.

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.1 km from Rolling Road Park
United States
Sandra
€110
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
View all properties

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 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

Hotels recommended for families near Rolling Road Park

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
€97
includes taxes & fees
8 Nov - 9 Nov
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 living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
€71
includes taxes & fees
19 Oct - 20 Oct
Red Roof Inn & Suites 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 bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.
A building with a balcony and large windows, surrounded by trees and a fence.

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
€146
includes taxes & fees
13 Oct - 14 Oct
First Floor Studio Apartment in Historic 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 laundry room with two front-loading washing machines, a drying rack, and a small cabinet above the machines.
A modern kitchen with a large island, white cabinetry, and a view of the city.

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
€313
includes taxes & fees
13 Oct - 14 Oct
Newly restored apartment in the heart of 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 campfire in a stone fire pit by a lakeside at sunset.

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
€110
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.
A living room with a glass-top coffee table, a blue sofa, a patterned armchair, and a television on a wooden stand.
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
13 Oct - 14 Oct
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 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 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.

Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
€159
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
Marina
An outdoor event area with round tables and a view of the water.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
€151
includes taxes & fees
18 Oct - 19 Oct
Hyatt Place Kent Narrows & Marina

Top Rolling Road Park Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"The room was clean, staff was helpful for the most part with a few exceptions, wasn’t able to get breakfast because the lady snatched everything up quickly even after seeing me wait for someone to finish making their waffles,and wasn’t many options for breakfast anyways"
Kashay 7-night trip
Posted 3 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

10/10 Excellent
"Stayed in October. Room was clean and had a great view of the water. No microwave or coffee in the room but it was always available at the end of the hall. Keyless entry was convenient . Cell service is terrible though had to go to the windows to have any service."
Jennifer 2-night trip
Posted 5 hours ago
The Lodge at Great Oak Landing
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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

10/10 Excellent
"Little weird driveway"
Anto 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"The checkin was smooth though we waited for the desk staff to want to move to check us in. The room was immaculate and looked newly renovated. Conveniently across the street from great restaurants"
Cynthia 1-night trip
Posted 18 hours ago
Best Western Kent Narrows Inn
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"
Shannon 1-night trip
Posted 1 day ago
The Inn at Chesapeake Bay Beach Club
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

8/10 Good
"good"
Hidenori 2-night trip
Posted 1 day ago
Hampton Inn Baltimore/White Marsh

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.
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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 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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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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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.
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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 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 exploring the galleries in Sumner Hall during your travels 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. 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.