Greencastle holiday lettings

We found 34 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Greencastle that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and cable TV. 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.

Holiday rentals with weekly discounts - Greencastle

Showing deals for:6 Feb - 13 Feb

Image gallery for Beautiful Mansion in the Country & Wedding Venue

Outdoor dining
9.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Beautiful Mansion in the Country & Wedding Venue

Waynesboro, PA

8% off
Price is £10,359
for 7 nights, 1 home
£1,480 per night
includes taxes & fees
Beautiful Mansion in the Country & Wedding Venue

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Why visit Greencastle

  • Outdoor Adventures: Enjoy activities like skiing and exploring local parks amidst stunning natural landscapes.
  • Cultural Heritage: Visit historic colleges and universities that reflect the rich history of the area.
  • Charming Atmosphere: Experience the friendly locals and quaint fishing village vibe that Greencastle offers.
  • Diverse Accommodations: Choose from a variety of holiday rentals, including charming cottages and cosy cabins.
  • Family-Friendly Activities: Engage in excursions and activities suitable for both families and history enthusiasts.

Popular types of accommodation in Greencastle

If you're exploring Greencastle for your next getaway, you'll find a delightful range of holiday rentals to suit your needs. Our most sought-after accommodations include houses, charming cottages, and cosy cabins. Whether you're searching for Greencastle holiday rentals, apartments in Greencastle, or the inviting Castle Inn apartments, we have various options to ensure a memorable stay in this picturesque location.

  • Houses: The top choice for visitors to Greencastle, offering spacious and comfortable accommodations ideal for families or groups.
  • Cabins: A close second, these cosy retreats provide a perfect escape into nature for those seeking tranquillity.
  • Cottages: Charming and quaint, these delightful options are perfect for a romantic getaway or a peaceful retreat.
  • Apartments: Convenient and often centrally located, apartments offer a home-away-from-home experience.
  • Chalets: These alpine-style lodgings provide a unique and picturesque setting for your stay.**

Top attractions in and around Greencastle

Greencastle offers a delightful blend of outdoor adventures and cultural experiences, making it ideal for a varied holiday. Visitors can enjoy activities like skiing and exploring local parks, as well as visiting historic colleges and universities. The area's attractions cater to those seeking adventure and a taste of local heritage, ensuring an enjoyable stay for all types of travellers.

  • Wilson College: A historic institution with beautiful architecture and an inviting campus, Wilson College offers a glimpse into American higher education's past, surrounded by lush gardens and cultural events.
  • Washington County Museum of Fine Arts: This art museum showcases an impressive collection of fine art, hosting exhibitions that highlight both local and international artists, all within a serene park setting.
  • Martins Mill Bridge: A charming historic bridge that serves as a picturesque landmark, perfect for a leisurely stroll while enjoying the rich history and scenic views of the area.

Things to do recommended for couples

For a romantic getaway in Greencastle, explore the snowy slopes at Whitetail Ski Resort or enjoy a delightful wine tasting at Knob Hall Winery. For a thrilling experience, take a ride on the Magic Carpet Ski Lift, embracing adventure together amidst stunning winter views.

Things to do recommended for families

Families can have a fantastic time at Cluggy's Family Amusement Center, an exciting arcade adventure zone located 6.8km from Greencastle. For a more tranquil experience, Norlo Park offers a lovely recreational area just 7.5km away, perfect for relaxation and wellness.

Things to do recommended for groups

Groups visiting Greencastle can enjoy a cultural evening at the Maryland Theater, experience thrilling races at Hagerstown Speedway, and explore the vibrant Pennsylvania Dutch Market for a taste of local commerce and cuisine.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Greencastle with a group: Think about how many bedrooms you'll require, as well as any amenities you might desire, such as a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Greencastle with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Greencastle: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Greencastle: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You may also want to include amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Greencastle

Greencastle, Pennsylvania, offers a delightful mix of adventure and relaxation, perfect for families and history enthusiasts alike. Explore the charming fishing village atmosphere, with its stunning natural landscapes and friendly locals. Nearby, you can enjoy outdoor activities and excursions that highlight the area's beauty. Whether you're seeking a budget-friendly getaway or a more lavish experience, Greencastle provides a welcoming vibe that's sure to make your holiday memorable.

  • Hagerstown: Located a mere 6.2km from Greencastle, Hagerstown is a vibrant city offering a delightful blend of outdoor adventure and family-friendly experiences. Visitors can indulge in skiing at nearby resorts or explore the picturesque landscapes of the national state park. With its beautiful lake and rich historic sites, Hagerstown promises a memorable getaway for those seeking both excitement and relaxation in a scenic setting.
  • Chambersburg: Just 6.8km from Greencastle, Chambersburg is a charming city perfect for outdoor enthusiasts and scenic adventurers. The area boasts excellent educational facilities and recreational areas, making it an ideal spot for families. Visitors can enjoy skiing activities and explore the stunning national state park, as well as the lovely lake and esteemed historic college university nearby, ensuring a captivating experience for all.
  • State Line: Nestled in close proximity to Greencastle, State Line is a quaint village that offers a serene escape for couples and nature lovers alike. The area is renowned for its stunning scenery and outdoor recreational opportunities, including lovely parks and tranquil lakes. With its romantic charm and historic sites, State Line invites travellers to unwind and explore the beauty of this picturesque setting.

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 SunnyAverageAverage
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 HighSlightly High
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 simple

Are you hoping to cut costs on your next holiday? Being flexible with your travel dates can often lead to significant savings, as prices tend to vary. Additionally, opting for a longer stay frequently results in even better deals. To discover the perfect Vrbo accommodation that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new adventures, pick up from where you last stopped, and manage your travel arrangements with ease. You can now access your previously saved and booked properties in the Potential, Upcoming, or Current Trips sections. To make the most of the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical area of Greencastle awaits your stay

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

Activities and attractions in Greencastle

Do you want to discover attractions to visit in the area? Venture out of your holiday home and experience everything that Greencastle has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Carroll Valley Resort Golf Courses (18.8 mi / 30.2 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 active traveller or just want to take in the scenery, Greencastle is a great spot to appreciate mother nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Marty Snook County Park (12.7 mi / 20.5 km)

Transport to and around Greencastle

The nearest airport is in Hagerstown, MD (HGR-Hagerstown Regional), located 5.9 mi (9.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into 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 when booking a holiday rental?
When considering a holiday rental in Greencastle, Pennsylvania, the downtown area stands out as an excellent choice. This charming locale offers a delightful mix of quaint shops, local eateries, and historical sites. Staying in the heart of downtown allows you to enjoy easy access to the Greencastle-Antrim Museum, where you can delve into the rich local history, and the beautiful Greencastle Town Park, great for leisurely strolls or picnics.

Another appealing neighbourhood is the surrounding countryside, where you'll find a variety of properties set amidst picturesque landscapes. This area not only provides a serene escape but also places you close to the stunning South Mountain State Park. Here, outdoor enthusiasts can enjoy hiking and exploring nature trails, making it a fantastic spot for those who appreciate the great outdoors.
How much does it cost to rent a holiday home in Greencastle?
Prices for holiday 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 holiday 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 holiday rental accomodation in Greencastle?
In Greencastle, cottages are a popular choice among holiday rentals, with several available throughout the area. These charming properties often feature traditional decor, fully equipped kitchens, and cosy living areas, providing a warm and inclusive setting for travellers. Many cottages also come with outdoor spaces, such as porches or gardens, ideal for relaxing after exploring the local attractions.
Are there any family house rentals in Greencastle?
In Greencastle, Pennsylvania, there are several family house rentals available, making it an inviting destination for those travelling with children. The area features spacious homes that typically offer multiple bedrooms, allowing for ample accommodation for families. Many of these properties come equipped with full kitchens, providing a convenient option for preparing meals together after a day of exploring.
Can I find long-stay holiday rentals in Greencastle?
A long-stay holiday rental in Greencastle is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Greencastle?
In Greencastle, Pennsylvania, there are several pet-friendly house rentals available for travellers looking to enjoy a getaway with their furry companions. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.
Are there any remote work holiday rentals in Greencastle?
In Greencastle, Pennsylvania, there are several holiday rentals that cater to remote workers. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated workspaces with desks and desk chairs, ensuring a comfortable environment for productivity. The town itself offers a peaceful atmosphere, making it an ideal location for those looking to blend work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greencastle holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Greencastle with parking available—perfect for families or travellers 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 holiday rental amenities include microwaves, coffee makers, and cookware such as dishware and utensils, ensuring guests have the essentials for self-catering. Many rentals also feature dining tables, allowing for communal meals and gatherings. Additionally, dishwashers are commonly found in these properties, making it convenient for guests to clean up after cooking.
When is the best time to visit Greencastle for a holiday rental?
July is the most popular time to visit Greencastle, Pennsylvania, making it an ideal choice for holiday rentals. This month falls within the peak season, which runs from May to July, and offers a vibrant atmosphere brimming with outdoor activities and local events. Visitors can enjoy pleasant temperatures, typically in the mid to high 20s Celsius, great for exploring the charming downtown area, participating in local festivals, or simply unwinding in the scenic parks.

The summer months are particularly welcoming for travellers, as they provide ample opportunities for hiking, biking, and enjoying the natural beauty that surrounds Greencastle. The lush landscapes and historical sites are easily accessible, ensuring a comfortable experience for those who enjoy outdoor activities and sightseeing.

If you're looking for a more budget-friendly option, consider visiting in November. This month allows for a quieter experience, where you can appreciate the serene beauty of the changing season without the crowds. It's a wonderful time for leisurely strolls and enjoying the local culture at a more relaxed pace.
How early should I book a Greencastle holiday rental?
Book your Greencastle holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Greencastle home rental booking on Vrbo?
To find Greencastle holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Greencastle holiday 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.

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