Holiday rentals near Rolling Road Park
We found 52 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Rolling Road Park, take a look at private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Rolling Road Park
Showing deals for:19 Dec - 26 Dec
Image gallery for Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.8 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Chestertown, MD
8% off
Price is AU$15,487
for 7 nights, 1 home
AU$2,212 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Rolling Road Park
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Sleeps 10 · 3 bedrooms · 2 bathrooms
10 out of 10
exceptional
(24 reviews)
Top rated rentals - Rolling Road Park
Fantastic place
10 out of 10
exceptional
(24 reviews)
had a great time
George B.
Stayed Apr 2025
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value