Pittsville vacation rentals

We found 21 vacation rentals — enter your dates for availability

Discover a selection of 5 cabins and other vacation rentals in Pittsville that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Pittsville

Why visit Pittsville

  • Outdoor Adventures: Enjoy a variety of outdoor activities in Pittsville's scenic parks and natural areas, perfect for families and couples.
  • Charming Neighborhoods: Explore welcoming local neighborhoods filled with friendly residents and picturesque views.
  • Day Trip Access: Use Pittsville as a base for day trips to the stunning beaches of the Delmarva Peninsula.
  • Family-Friendly Activities: Discover numerous attractions and entertainment options suitable for all ages.
  • Affordable Accommodations: Choose from a range of affordable vacation rentals, including cozy homes and apartments.

Popular types of accommodation in Pittsville

Planning a getaway to Pittsville? You're in for a treat. Discover a range of affordable vacation rentals, from private homes to cozy condos and apartments. Whether you're searching for cheap apartments for rent or a charming house to call your own during your stay, Pittsville has something for every traveler. Enjoy the comfort and convenience of top-notch accommodations while exploring all that this delightful destination has to offer.

  • Houses: The top choice for visitors to Pittsville, these homes offer spacious and comfortable living for families and groups.
  • Condos: A popular option, condos provide modern amenities and convenient locations for an enjoyable stay.
  • Apartments: Ideal for solo travelers or couples, apartments offer a cozy and budget-friendly option for your trip.
  • Cottages: These quaint and charming homes are perfect for a peaceful getaway in a picturesque setting.
  • Villas: Luxurious and spacious, villas are great for those seeking a more upscale vacation experience.**

Top attractions near Pittsville

Pittsville, Maryland, is perfect for outdoor adventures and family or romantic getaways. Visitors can enjoy various attractions, including urban parks, entertainment facilities, and scenic esplanades. Whether you're seeking cultural experiences or simply exploring the charming town, Pittsville offers something for everyone. Don't miss the chance to discover local points of interest and immerse yourself in the natural beauty and community spirit of the area.

  • Ocean City Boardwalk: Located 18 miles from Pittsville, this vibrant esplanade is perfect for families and couples alike, offering stunning ocean views, amusement rides, and an array of shops and eateries, all infused with a lively beach atmosphere.
  • Salisbury University: Just 11 miles away, this historic university boasts a rich cultural vibe, featuring beautiful architecture, art galleries, and engaging events that showcase the local arts and community spirit.
  • Wor-Wic Community College: Situated 5 miles from Pittsville, this modern college offers a dynamic city feel, with a focus on career-oriented programs and community engagement, making it a hub for local learning and development.

Things to do recommended for couples

For a romantic getaway in Pittsville, visit Costa Ventosa Vineyard and Winery for a charming wine experience just 9 miles away. Enjoy a delightful meal at The Hen House, 14 miles from town. Don’t miss Bordeleau Winery, 19 miles away, for more enchanting moments together.

Things to do recommended for families

Your family can enjoy a thrilling day at Arthur W. Perdue Stadium for sports excitement, splash around at Frontier Town Water Park and Golf for adventure, or test your skills at Coco's Funhouse arcade, all within a short drive from Pittsville, Maryland.

Things to do recommended for groups

Shop and enjoy entertainment at the Centre at Salisbury, just 8 miles from Pittsville. Experience the romantic vibes at Seacrets Distilling Company, 19 miles away, or hit the greens at The Bay Club golf course, located 10 miles from town. Perfect activities for your group getaway.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pittsville

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences in the filters. Here are some helpful booking tips for using Vrbo.

  • Traveling to Pittsville with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily narrow down your options for all of these preferences and more on Vrbo.
  • Traveling to Pittsville with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference.
  • Taking your pets with you to Pittsville: For many families, a vacation isn’t truly satisfying without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pittsville: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near Pittsville

Pittsville, Maryland, offers a perfect blend of outdoor adventures and family-friendly activities. Explore the charming neighborhoods nearby, where you'll find a welcoming atmosphere filled with friendly locals and scenic views. With its central location, Pittsville serves as an ideal base for day trips to the beautiful Delmarva Peninsula and its stunning beaches. Whether you're seeking romantic spots or recreational fun, this quaint city promises an unforgettable vacation experience.

  • Parsonsburg: Located a mere 3 miles from Pittsville, Parsonsburg is a charming city ideal for those seeking outdoor adventures, romantic getaways, or family experiences. The town offers a variety of activities, including educational excursions and thrilling motor racing events. Nature enthusiasts will enjoy the nearby beaches and family-friendly beach areas, while history buffs can visit the historic college university that adds cultural depth to the locale. With its welcoming atmosphere, Parsonsburg is perfect for a day trip filled with exploration and fun.
  • Willards: Just 4 miles from Pittsville, Willards is another great destination for families and outdoor lovers. This vibrant city is known for its recreational areas and shopping opportunities. Visitors can stroll along the scenic boardwalk or relax at the esplanade while soaking up the sun. The proximity to beautiful beaches, including family-oriented options, makes Willards an excellent choice for a leisurely day spent enjoying nature and engaging in local activities. Whether you're looking for a peaceful retreat or a fun-filled day, Willards has something for everyone.
  • Powellville: Situated 5 miles away from Pittsville, Powellville is a delightful city that focuses on outdoor and beach experiences. Families can delight in the sandy shores, while water enthusiasts can explore the local marina. Powellville also features a stadium, making it a great spot for catching local events or enjoying outdoor sports. With its relaxed vibe and natural attractions, Powellville invites visitors to unwind and make lasting memories in a beautiful setting.

Best time to go to Pittsville

If you're planning a trip to Pittsville, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.9°F (2.7°C)Light RainMostly SunnyAverageSlightly Low
February39.7°F (4.3°C)Light RainMostly SunnyAverageSlightly Low
March45.7°F (7.6°C)Light RainMostly SunnyAverageSlightly Low
April55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
May64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
June72.9°F (22.7°C)Light RainMostly SunnyModerately HighSlightly High
July78.1°F (25.6°C)Light RainMostly SunnyModerately HighSlightly High
August76.3°F (24.6°C)Light RainMostly SunnyModerately HighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October61.0°F (16.1°C)Light RainMostly SunnyModerately LowAverage
November49.5°F (9.7°C)Light RainMostly SunnyModerately LowAverage
December42.6°F (5.9°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Are you eager to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy even greater savings. To discover a Vrbo property that suits your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. It's truly rewarding to take on the role of organizer. Become a part of our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on qualifying stays. Sign up today and begin enjoying the benefits.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly area for you to plan new trips, resume your previous ones, or review and organize your travel arrangements. You can easily access the properties you've saved or booked, which are sorted into categories like Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Pittsville getaway

Learn about the unique charm of Pittsville with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. 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 top things to see and do in the area? Venture out of your cozy vacation rental and check out everything that makes Pittsville a one-of-a-kind vacation spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Salisbury Zoo (9.5 mi / 15.3 km)
  • 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)
  • Ocean City Golf Club (16.2 mi / 26.1 km)
  • Bayside Resort Golf Club (17 mi / 27.3 km)

Exploring the natural features in Pittsville

Whether you're an active traveler or just want to appreciate the scenery, Pittsville is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Assawoman Bay (17.7 mi / 28.4 km)
  • Inlet Park (18.2 mi / 29.3 km)
  • Ocean City Inlet (18.3 mi / 29.4 km)
  • Ocean City Beach (18.4 mi / 29.6 km)
  • James Branch Nature Preserve (10.9 mi / 17.6 km)
  • Pemberton Historical Park (12.9 mi / 20.7 km)

Transportation 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 center. If you can't find a flight that works for your travel itinerary, you could book a flight to Ocean City, MD (OCE-Ocean City Municipal), which is 17 mi (27.4 km) away.

Frequently asked questions

What is the best area to stay in Pittsville when booking a vacation rental?
When considering a vacation rental in Pittsville, Maryland, a popular area to stay is near the town center, which offers a charming small-town atmosphere and convenient access to local amenities. This area is particularly appealing for those who enjoy a laid-back vibe while still being close to attractions.

Staying in the heart of Pittsville allows you to explore the beautiful surroundings, such as the nearby Pocomoke River State Park, which is superb for outdoor enthusiasts interested in hiking, fishing, and birdwatching. Additionally, the historic charm of the local downtown area, with its quaint shops and eateries, invites visitors to take leisurely strolls and immerse themselves in the community's culture.

In terms of vacation rentals, you can typically find a variety of properties in this central area, ranging from cozy cottages to larger family homes, allowing for options that suit different group sizes and preferences.
How much does it cost to rent a vacation home in Pittsville?
Prices for vacation rentals in Pittsville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pittsville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pittsville vacation house rentals?
You can find great discounts on house rentals in Pittsville on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Pittsville?
In Pittsville, cabins are the most popular type of vacation rental, with several options available. These cabins are typically situated in serene, wooded areas, offering a tranquil escape for travelers looking to enjoy nature. Most cabins come equipped with essential amenities such as fully stocked kitchens, cozy living rooms, and outdoor spaces like decks or porches, ideal for taking in the peaceful surroundings.
Are there any family house rentals in Pittsville?
In Pittsville, Maryland, there are some family-friendly house rentals available, offering a comfortable stay for visitors. The area features spacious homes with amenities such as full kitchens for preparing meals, cozy living rooms for family gatherings, and outdoor areas where children can play or enjoy a barbecue.

Located near the scenic Wicomico River, travelers can take advantage of outdoor activities like fishing, kayaking, and hiking in the surrounding nature. Additionally, the town is just a short drive from the vibrant attractions of Salisbury, including parks and local dining options, making it a convenient base for exploring the Eastern Shore.
Can I find long-stay vacation rentals in Pittsville?
A long-stay vacation rental in Pittsville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Pittsville?
In Pittsville, travelers can find several pet-friendly house rentals that cater to various needs. Many of these homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups traveling with pets. The area offers a peaceful, rural setting that allows for easy access to outdoor activities and nearby attractions.

For those looking to explore, the nearby Pocomoke River State Park provides fantastic opportunities for hiking, kayaking, and enjoying nature with pets. The park features beautiful trails and picnic areas, great for a day out with your furry friends.
Are there any remote work vacation rentals in Pittsville?
In Pittsville, Maryland, travelers seeking remote work vacation rentals will find several options available. The area provides a peaceful environment suitable for productivity, with many properties featuring dedicated workspaces, such as desks and ergonomic chairs, allowing for a comfortable working experience. Additionally, amenities like high-speed Wi-Fi ensure connectivity for remote tasks.

Pittsville is conveniently located near the scenic Pocomoke River and the charming towns of Salisbury and Snow Hill, offering opportunities for outdoor activities and local exploration during downtime. Visitors can enjoy access to parks and nature trails, making it a pleasant destination for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pittsville with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pittsville?
In Pittsville, popular vacation rental amenities include stunning lake views, which add a serene touch to the stay. Many rentals offer free self-parking, making it convenient for guests traveling by car. For those who enjoy water activities, boat docks are a common feature, allowing easy access to the nearby waterways. Additionally, some properties provide amenities for pet owners, such as dog exercise areas, ensuring that furry friends can enjoy the trip too. Cozy fireplaces are also popular, creating a warm and friendly space, great for relaxing after a day of exploring the beautiful surroundings of Maryland's Eastern Shore.
When is the best time to visit Pittsville for a vacation rental?
The best time to visit Pittsville for a vacation rental is during the peak summer months of June to August, with July being particularly popular among travelers. This season attracts travelers, drawn by the warm weather and a variety of outdoor activities. Expect temperatures ranging from the mid-70s to the low 90s Fahrenheit, superb for enjoying the beautiful natural surroundings.

During this lively period, visitors can partake in numerous recreational options such as hiking, fishing, and exploring local parks. The vibrant atmosphere in Pittsville fosters a sense of community, making it an ideal setting for family gatherings or friendly getaways. Whether you're wandering through charming local shops or savoring the fresh flavors at nearby eateries, there's always something to engage in during these sun-soaked months.

If you're considering a more budget-friendly option, October is a delightful time to visit Pittsville. The weather remains pleasant, with temperatures often in the mid-60s to low 70s Fahrenheit, making it great for leisurely walks and enjoying the beautiful fall foliage. This quieter month offers a chance to experience the area without the hustle and bustle of the peak season, allowing for a more relaxed exploration.

Ultimately, your choice of when to visit Pittsville will depend on whether you prefer the energetic vibe of summer adventures or the peaceful charm of fall colors.
How early should I book a Pittsville vacation rental?
Book your Pittsville vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Pittsville home rental booking on Vrbo?
To find Pittsville vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pittsville vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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