Holiday rentals near Roundtop Park

We found 48 holiday rentals — enter your dates for availability

Find the perfect private holiday rental that's close to Roundtop Park. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Roundtop Park

Showing deals for:26 Dec - 2 Jan

Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Exterior
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, MD

17% off
Price is AU$4,412
for 7 nights, 1 cottage
AU$630 per night
includes taxes & fees
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value