Pittsville, Maryland holiday accommodation: short-term house rentals & properties

Discover a selection of 5 cabins and other holiday rentals in Pittsville that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include a garden and pool. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find the best place to stay - Pittsville

Large estate & cottage with private pool, firepits, & game room

Sleeps 26 · 8 bedrooms · 5+ bathrooms

Beautifully renovated bayfront home with deck, game room, fireplace & EV charger

Sleeps 13 · 6 bedrooms · 4 bathrooms

One Level Waterfront Home-Pet Friendly - 5 Pools- Golf-Sleeps 8- Self Check-In !

Sleeps 8 · 3 bedrooms · 2 bathrooms

Dog-friendly, waterfront home with dock, fireplace, pools & great location

Sleeps 6 · 3 bedrooms · 2 bathrooms

Remodeled, Waterfront Home with Beautiful View, Dock, Large Deck - 1 Dog OK

Sleeps 7 · 3 bedrooms · 2 bathrooms

Find spaces that suit your style

House

Condo/Apartment

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

Book a holiday rental for your Pittsville getaway

Learn about the unique charm of Pittsville with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Pittsville

Are you looking for attractions to see in the area? Venture out of your holiday home and check out everything that makes Pittsville a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Ocean Pines Golf and Country Club (14.4 mi / 23.3 km)
Baywood Greens Golf Course (14.6 mi / 23.5 km)
Frontier Town Water Park and Golf (16.1 mi / 25.9 km)
Bayside Resort Golf Club (17 mi / 27.3 km)
Trimper's Rides (18.2 mi / 29.3 km)
Jolly Roger at the Pier (18.3 mi / 29.5 km)

Exploring the natural features in Pittsville

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Pittsville is a great place to get out in nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

Ocean City Beach (18.4 mi / 29.6 km)
Inlet Park (18.2 mi / 29.3 km)
Assateague State Park (18.5 mi / 29.7 km)
Trap Pond State Park (9.6 mi / 15.5 km)
Assawoman Bay (17.7 mi / 28.4 km)
Pocomoke River State Park (17.7 mi / 28.5 km)

Transport to and around Pittsville

The nearest airport is in Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), located 6.7 mi (10.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Ocean City, MD (OCE-Ocean City Municipal), which is 17 mi (27.4 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Pittsville?

Length of stay, season and property type are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy cabins to expansive villas, all Stayz holiday homes offer incredible value.

How much does it cost to rent a beach house in Pittsville?

Prices for beach houses in Pittsville may vary depending on the type and size of the property and when you're travelling. All you need to do is enter your travel dates into Stayz and how many guests to see your options and prices. From there you can use the filters to tailor your search by nearby activities, amenities, ratings and more.

What are the top attractions for families in Pittsville?

There's a ton of cool things to do and see with the family in Pittsville, such as:

Eastern Shore Baseball Hall of Fame Museum
Cocos Funhouse
Ward Museum of Wildfowl Art

How old do you have to be to rent a holiday home in Pittsville?

The minimum age can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Pittsville you want to book. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Pittsville for?

How long you can book a holiday home in Pittsville is down to the property. Just enter your chosen dates to view a list of options offering extended stays. With plenty of amenities like full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover a perfect place to call your home away from home in Pittsville.