Greencastle vacation rentals

We found 39 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Greencastle that are perfect for your trip. Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, like WiFi and cable TV. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Greencastle

Why visit Greencastle

  • Outdoor Adventures: Greencastle offers excellent opportunities for skiing, hiking, and exploring its stunning landscapes in nearby parks.
  • Rich History: Engage with the town's heritage by visiting local colleges and historical sites that reflect its past.
  • Charming Neighborhoods: Discover the friendly atmosphere of Greencastle's rolling hills and inviting communities.
  • Variety of Accommodations: Choose from spacious homes, cozy cabins, or charming cottages to feel at home during your stay.
  • Proximity to Other Cities: Use Greencastle as a base to explore nearby vibrant cultural and natural attractions.

Popular types of accommodation in Greencastle

Discover the charm of Greencastle with a variety of vacation rentals to suit your needs. From spacious houses and cozy cabins to charming cottages, there's something for everyone. Whether you're searching for Greencastle apartments or exploring new properties, our listings provide transparent options for a perfect getaway. Enjoy the comfort and reassurance of a home away from home while you explore the beauty of Greencastle, PA.

  • Houses: These are the top choice for visitors seeking a spacious and comfortable stay, perfect for families or groups in Greencastle.
  • Cabins: A cozy option surrounded by nature, ideal for those looking to unwind and experience the great outdoors.
  • Cottages: Charming and quaint, these rentals offer a homey atmosphere for a relaxing getaway.
  • Apartments: Convenient and modern, perfect for travelers seeking easy access to local attractions.
  • Chalets: A delightful option for those wanting a unique, alpine-style experience in Greencastle.**

Top attractions in and around Greencastle

Greencastle, Pennsylvania, offers a fantastic blend of outdoor adventures and cultural experiences, making it perfect for tourists seeking skiing, hiking, and exploration. Visitors can enjoy the stunning landscapes of nearby national and state parks, delve into the rich history at local colleges and universities, or relax in beautiful parks. This charming town is ideal for those looking to immerse themselves in nature and history while enjoying exciting activities.

  • Mercersburg Academy: A prestigious historic college, Mercersburg Academy showcases beautiful architecture and lush grounds, offering visitors a glimpse into its rich educational history and vibrant campus culture.
  • Renfrew Museum and Park: This charming historic house and park features fascinating exhibits on local history, combined with serene walking trails and gardens, making it a perfect spot for both learning and relaxation.
  • Martins Mill Bridge: A picturesque historic bridge in Greencastle, Martins Mill Bridge provides a scenic backdrop for photography and a peaceful place to enjoy the surrounding nature and history.

Things to do recommended for couples

For a romantic getaway in Greencastle, consider skiing at Whitetail Ski Resort or Expert's Choice for some adventure. Afterward, unwind at Knob Hall Winery, where you can enjoy the cozy atmosphere and indulge in fine wines together. It's the perfect blend of excitement and romance.

Things to do recommended for families

Your family will have a blast at Cluggy's Family Amusement Center, an exciting arcade adventure just 11 miles from Greencastle. For some relaxation, visit Norlo Park, a serene recreational area located 12 miles away, perfect for unwinding and enjoying nature together.

Things to do recommended for groups

Experience the vibrant atmosphere at the Pennsylvania Dutch Market, just 9 miles away. Enjoy a show at the Maryland Theater, located 10 miles from Greencastle, or hit the greens at Penn National Golf Course, 11 miles away, for some outdoor sports fun with friends.

*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 Greencastle

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to refine your search based on your top priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Greencastle with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Fortunately, you can easily filter for these options and more on Vrbo.
  • Traveling to Greencastle with young kids: Traveling with young kids can be quite demanding. It’s essential to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Greencastle: For many families, a trip isn’t truly finished without their beloved pet by their side. If this resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly properties offer amenities like food bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greencastle: If you're searching for vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Greencastle

Greencastle, Pennsylvania, offers a delightful mix of outdoor adventures and rich history, making it an ideal vacation spot. Travelers can explore the charming rolling hills and nearby neighborhoods, experiencing a family-friendly atmosphere that invites excursions and friendly interactions. With its proximity to other cities, Greencastle serves as a perfect base for discovering the surrounding area's vibrant culture and natural beauty, ensuring a memorable getaway for everyone.

  • Hagerstown: Hagerstown is a vibrant city located approximately 10 miles from Greencastle. Known for its outdoor adventures and family-friendly experiences, Hagerstown offers a range of activities from skiing at nearby resorts to exploring scenic national parks. Visitors can enjoy picturesque lakes and historic sites that highlight the rich history of the area. Whether you're hitting the slopes or enjoying a leisurely stroll through its parks, Hagerstown provides a delightful mix of recreation and relaxation for all ages.
  • Chambersburg: Situated about 11 miles from Greencastle, Chambersburg is a charming city that boasts stunning scenery and abundant outdoor activities. This destination is perfect for those seeking adventure, with educational opportunities and recreational areas that invite exploration. Visitors can delve into the area's natural beauty while also discovering historic colleges and universities. Chambersburg is a wonderful place to enjoy hiking, skiing, and the picturesque landscapes that define this part of Pennsylvania.
  • State Line: Nestled within the vicinity of Greencastle, State Line is a quaint village offering a romantic and scenic getaway. Ideal for outdoor enthusiasts, visitors can partake in various recreational activities while soaking in the village's natural beauty. Attractions in State Line include serene lakes and intriguing historic sites that add a touch of charm to your visit. It's an excellent spot for couples and nature lovers alike, providing a peaceful retreat just moments from the hustle and bustle of larger cities.

Best time to go to Greencastle

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly CloudyAverageSlightly High
February32.7°F (0.4°C)Light RainMostly SunnyAverageSlightly High
March40.8°F (4.9°C)Light RainMostly SunnySlightly HighSlightly Low
April51.6°F (10.9°C)Light RainMostly SunnySlightly HighSlightly Low
May61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainMostly SunnyAverageAverage
July75.2°F (24.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
September66.2°F (19.0°C)Light RainMostly SunnyAverageSlightly Low
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowAverage
November42.6°F (5.9°C)Light RainMostly SunnySlightly LowAverage
December35.4°F (1.9°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices often fluctuate. Plus, extending your stay can lead to even more significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board feature offers you a convenient way to plan new trips, pick up where you left off, and manage your travel arrangements with ease. You can easily access your saved and booked properties in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The historic area of Greencastle awaits your stay

Enjoy the history and other features of Greencastle. This welcoming and scenic city entices travelers with its restaurants and shopping. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Greencastle

Do you want to find things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Greencastle has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Penn National Golf Course (10.6 mi / 17.1 km)
  • Hagerstown Speedway (11.1 mi / 17.9 km)
  • Whitetail Ski Resort (11.4 mi / 18.4 km)
  • Monterey Country Club (14.1 mi / 22.8 km)
  • Liberty Mountain Ski Resort (19.2 mi / 30.8 km)
  • Adams County Winery (19.5 mi / 31.3 km)

Exploring the natural landscape of Greencastle

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Greencastle is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Cowans Gap State Park (17.7 mi / 28.5 km)
  • Greenbrier State Park (18.4 mi / 29.6 km)
  • Chesapeake and Ohio Canal (27.7 mi / 44.5 km)
  • Renfrew Museum and Park (9.5 mi / 15.3 km)
  • Norlo Park (11.6 mi / 18.7 km)
  • Pen Mar Park (12.7 mi / 20.5 km)

Transportation to and around Greencastle

The nearest airport is in Hagerstown, MD (HGR-Hagerstown Regional), located 5.9 mi (9.5 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 30 mi (48.3 km) away.

Frequently asked questions

What is the best area to stay in Greencastle, Pennsylvania, United States of America when booking a vacation rental?
When considering a vacation rental in Greencastle, Pennsylvania, the downtown area is an excellent choice. This vibrant neighborhood offers a charming small-town atmosphere, making it superb for visitors looking to immerse themselves in local culture. The downtown area features a variety of local shops, cafes, and restaurants, providing a delightful experience for those who enjoy exploring local flavors and crafts.

Additionally, the nearby Greencastle-Antrim Museum is a popular attraction that offers insights into the region's rich history and heritage. For outdoor enthusiasts, the proximity to parks and walking trails allows for plenty of opportunities to enjoy the natural beauty surrounding the town. The downtown area typically has a range of properties available, suiting different preferences and budgets.
How much does it cost to rent a vacation home in Greencastle?
Prices for vacation rentals in Greencastle 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 Greencastle 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 Greencastle vacation house rentals?
You can find great discounts on house rentals in Greencastle 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 Greencastle?
In Greencastle, vacation houses and mobile homes are the most popular types of rental accommodations, with several available throughout the area. These vacation houses typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many of these homes also feature outdoor spaces such as patios or gardens, superb for relaxing after a day of exploring local attractions. Mobile homes provide a different experience, often situated in serene settings, allowing guests to enjoy a more rustic and laid-back atmosphere.
Are there any family house rentals in Greencastle?
In Greencastle, Pennsylvania, there are several family-friendly house rentals available, offering a welcoming environment for groups. Visitors can find homes with spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces great for children to play. Many properties also provide amenities such as Wi-Fi and air conditioning to enhance comfort during your stay.

The town is situated near various attractions, including historical sites and parks, making it an excellent base for exploring the area. Families can enjoy outdoor activities and local events, ensuring a memorable experience for everyone.
Can I rent a vacation home with a pool or hot tub in Greencastle?
In Greencastle, Pennsylvania, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and recreation. The area offers a mix of charming neighborhoods, where you can find properties with private pools and hot tubs, ideal for unwinding after a day of exploring. Many rentals come equipped with amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, ensuring a pleasant stay. Additionally, some homes may include features like outdoor patios and barbecue grills, superb for family gatherings or enjoying warm evenings outdoors.
Can I find long-stay vacation rentals in Greencastle?
A long-stay vacation rental in Greencastle 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 Greencastle?
In Greencastle, travelers can find several pet-friendly house rentals that cater to those traveling with furry companions. Many of these properties come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces, great for enjoying the fresh air with pets.

The town itself is known for its welcoming atmosphere and proximity to various parks that provide opportunities for walks and outdoor activities. Nearby, the Greencastle Community Park features open green spaces and walking trails, making it an ideal spot for pet owners to enjoy leisurely strolls. Additionally, the surrounding countryside offers scenic views and trails that are suitable for hiking with pets, ensuring that both travelers and their animals can enjoy the natural beauty of the area.
Are there any remote work vacation rentals in Greencastle?
In Greencastle, Pennsylvania, there are several remote work vacation rentals available, making it an ideal choice for those looking to combine work and leisure. Many of these properties are equipped with essential amenities for remote work, including desks, free Wi-Fi, and comfortable seating arrangements. This ensures that travelers can maintain productivity while enjoying their stay in this charming town.

Greencastle offers a quaint atmosphere with local parks and cultural sites nearby, providing opportunities for relaxation after work hours. The surrounding area features beautiful landscapes, great for outdoor activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greencastle vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Greencastle 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 Greencastle?
In Greencastle, popular vacation rental amenities cater to comfort and convenience, with a focus on home-like features. Travelers can expect rentals equipped with kitchens, allowing for easy meal preparation and dining in. Many properties also include porches or lanais, providing a relaxing outdoor space to enjoy the fresh air. Decks or patios are common as well, great for gatherings or unwinding after a day of exploration. Additionally, many rentals offer dedicated workspaces, complete with desks and desk chairs, making it suitable for those who may need to catch up on work during their stay.
When is the best time to visit Greencastle for a vacation rental?
The peak travel season in Greencastle runs from May to July, making it an ideal time for travelers seeking vibrant outdoor experiences. July, in particular, stands out as the most popular month, where visitors can enjoy warm sunshine and a lively option. This season is great for exploring local parks, engaging in outdoor activities, and attending community events that highlight the charm of this Pennsylvania town.

During these months, temperatures typically range from the mid-60s to the high 80s Fahrenheit, creating comfortable conditions for sightseeing and recreational adventures. Whether you're hiking the scenic trails or enjoying a leisurely stroll through the historic downtown, the natural beauty of the area is on full display.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter pace, allowing you to experience the tranquil beauty of Greencastle as the fall foliage creates a stunning backdrop. It's an excellent time for cozy indoor activities, local dining experiences, and exploring the rich history of the area without the crowds.

Ultimately, your choice of when to visit Greencastle should align with your travel preferences.
How early should I book a Greencastle vacation rental?
Book your Greencastle 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.
What are the top attractions in Greencastle, Pennsylvania, United States of America?
In Greencastle, visitors can explore a variety of attractions that highlight the town's charm and history. The Greencastle Historic District features beautifully preserved buildings and offers a glimpse into the area's past. Nearby, the Greencastle-Antrim Museum provides insights into local history and culture, making it a great stop for history enthusiasts.

Outdoor lovers can enjoy the nearby parks, such as the Greencastle Community Park, which offers walking trails, playgrounds, and picnic areas, ideal for family outings. The surrounding countryside is also great for hiking and enjoying nature.

For those interested in local agriculture, the area is home to several farms and markets where visitors can purchase fresh produce and handmade goods. Additionally, the proximity to the Appalachian Trail offers opportunities for hiking and exploring the great outdoors.
Can I change or cancel my Greencastle home rental booking on Vrbo?
To find Greencastle 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 Greencastle 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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