Best Vacation Homes in Greencastle
Apartment
10.0(22 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
£108/Night
7 Nights - £755
House
10.0(1 Review)
6 Bedrooms
6 Baths
15 Guests
6200.01 ft²
- Fireplace/Heating
Pool- Pet Friendly
Parking
£530/Night
7 Nights - £3,707
Bed & Breakfast
10.0(229 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Parking
£120/Night
7 Nights - £840
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
Air Conditioner
£81/Night
7 Nights - £569
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1905.21 ft²
- Parking
Internet
Child Friendly
Sports/Activities
£225/Night
7 Nights - £1,576
House
8.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£65/Night
7 Nights - £454
House
7.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£106/Night
7 Nights - £740
House
6.4(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£147/Night
7 Nights - £1,031
Greencastle Luxury Rentals
House
9.8(9 Reviews)
6 Bedrooms
5 Baths
32 Guests
7500 ft²
Private Pool
Hot Tub- Fireplace/Heating
- Pool
£1,445/Night
7 Nights - £10,118
Condo
10.0(3 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£656/Night
7 Nights - £4,595
House
1 Bedroom
1 Bath
4 Guests
334 ft²
- Child Friendly
£595/Night
7 Nights - £4,163
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
6000 ft²
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
£568/Night
7 Nights - £3,973
House
10.0(13 Reviews)
6 Bedrooms
5 Baths
15 Guests
6200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
£557/Night
7 Nights - £3,897
£466/Night
7 Nights - £3,261
£401/Night
7 Nights - £2,804
Other
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Security/Safety
£363/Night
7 Nights - £2,539
Greencastle Pet Friendly Vacation Rentals
Apartment
4.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£94/Night
7 Nights - £658
House
3 Bedrooms
6 Baths
12 Guests
215.28 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
£75/Night
7 Nights - £527
Hotel
9.4(553 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Pet Friendly
£96/Night
7 Nights - £670
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£99/Night
7 Nights - £695
New
Ski Chalet
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
£113/Night
7 Nights - £793
Apartment
10.0(13 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£102/Night
7 Nights - £714
Cottage
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
325 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£108/Night
7 Nights - £754
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
255 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£151/Night
7 Nights - £1,060
Greencastle Large Vacation Homes
Condo
9.4(23 Reviews)
2 Bedrooms
1 Bath
13 Guests
1087 ft²
- Hot Tub
Skiing- Fireplace/Heating
- Pool
£134/Night
7 Nights - £937
House
8.5(2 Reviews)
2 Bedrooms
1 Bath
13 Guests
1087.15 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Balcony/Terrace
£246/Night
7 Nights - £1,721
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£246/Night
7 Nights - £1,722
House
9.8(27 Reviews)
4 Bedrooms
3 Baths
10 Guests
1788 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£229/Night
7 Nights - £1,601
House
9.0(4 Reviews)
4 Bedrooms
1 Bath
10 Guests
2000 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
£193/Night
7 Nights - £1,350
House
7 Bedrooms
2 Baths
13 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£340/Night
7 Nights - £2,383
House
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£140/Night
7 Nights - £983
House
10.0(10 Reviews)
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£227/Night
7 Nights - £1,592
Why Choose Rent By Owner for your Greencastle Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Greencastle
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal changes in this destination influence the local ambiance and activities, making it ideal for planning your stay in this charming area.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for outdoor activities and exploring the scenic countryside of this destination.
Average Temperature Daytime: 85°F - Nighttime: 65°F
Fall (September to November)
This season offers vibrant foliage and pleasant temperatures, making it an excellent time to enjoy the area's natural beauty and peaceful surroundings.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler weather that creates a cozy atmosphere, perfect for relaxing in your rental while enjoying the region's serene winter landscape.
Average Temperature Daytime: 40°F - Nighttime: 25°F
Spring (March to May)
In spring, the area awakens with blooming flowers and mild weather, offering a quieter time to visit before the peak summer season begins.
Average Temperature Daytime: 60°F - Nighttime: 40°F
Weekly Weather Forecast for Greencastle
How to Book Your Greencastle Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Greencastle
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for sunset meals in the region’s scenic surroundings.
- Relax by a private or shared swimming pool, ideal for cooling off during warm summer days.
- Take advantage of spacious yards or gardens for outdoor activities and family fun.
- Make use of outdoor fire pits for cozy evenings under the stars.
- Benefit from access to hiking trails or nature walks directly from the property.
- Utilize covered decks or patios to unwind while enjoying fresh air and picturesque views.
- Play outdoor sports or games in well-maintained, open outdoor spaces.
Top Attractions Around Greencastle
What attractions are nearby?
During your stay, you'll find plenty of outdoor activities and local attractions nearby to explore, offering a memorable experience in this charming part of Pennsylvania.
Family Activities
- Green Castle County Park: Explore this expansive park offering family-friendly walking trails, picnic areas, and open spaces perfect for outdoor activities during your stay.
- Western Maryland Railroad Heritage Museum: Discover local history through engaging exhibits and vintage train displays that captivate visitors of all ages in the region.
- Burning Bush Farm: Experience farm life firsthand with seasonal hayrides, animal encounters, and other family-oriented outdoor fun close to your accommodation.
- Deer Creek Overlook: Enjoy scenic views and nature walks at this peaceful overlook, ideal for a relaxing family outing while exploring the area's natural beauty.
Adult Activities
- Explore the Antietam Creek Trail: Enjoy scenic walks or bike rides along this popular trail, offering a peaceful way to experience the natural beauty of the area.
- Visit the local wineries and breweries: Sample regional wines and craft beers at nearby wineries and breweries, perfect for relaxed adult outings.
- Discover historical sites in the region: Immerse yourself in the area's rich history by touring notable landmarks and museums that showcase its heritage.
- Attend cultural events and festivals: Participate in seasonal festivals and community events that highlight local traditions and entertainment here in the region.
Other Places to Stay in Greencastle, PA
Antrim Township
Greencastle Coffee Roasters
Shady Grove
Martins Mill Bridge
State Line
Williamson
Greencastle Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take the time to discover the area’s charming eateries and local markets to enjoy authentic regional flavors during your stay.
- Plan Outdoor Activities: Make the most of the scenic surroundings by scheduling outdoor pursuits such as hiking, biking, or leisurely walks through nearby parks.
- Visit Nearby Attractions: Use your vacation rental as a base to explore hidden gems and cultural sites that showcase the region’s rich history and natural beauty.
- Connect with the Community: Engage with local events or markets to experience the area's welcoming atmosphere and gain insider tips for your visit.
Transportation Options
- Greencastle Area Transit Authority (GATA): This local bus service provides convenient transportation options for exploring the region surrounding your vacation rental.
- Car Rentals: Numerous car rental agencies in the area offer flexibility and ease for sightseeing and daily outings during your stay.
- Taxi Services and Rideshares: Taxis and rideshare apps like Uber and Lyft are readily available for quick and reliable transportation around town.
- Biking and Walking: The region features scenic bike trails and walkable streets that allow you to enjoy the natural beauty of this destination at a leisurely pace.
Local Customs Options
- Pennsylvania Dutch Traditions: You may notice local craftsmanship and culinary influences rooted in Pennsylvania Dutch culture, reflecting a warm, community-oriented spirit here.
- Historical Celebrations: Participating in or observing regional festivals and parades offers insight into the area's rich history and friendly community customs.
- Farmers' Market Etiquette: Engaging with vendors at local markets follows a tradition of supporting regional farmers and fresh produce, a common practice in this area.
- Religious Observances: Respect for church services and events is customary here, highlighting the region’s strong religious heritage and community values.
Frequently Asked Questions About Greencastle?
1. What are the top vacation rentals in Greencastle?
There are a lot of options in Greencastle. If you plan on staying in the Greencastle area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greencastle:
- The Amberson House Bed & Breakfast
- Cedar Hill Cottage, the Perfect Getaway in Chambersburg PA
- UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
- Country Home with a view of the Mountains and Whitetail Ski Resort
- Visiting the area on a work assignment. Check out our multi day discounts.
- Spacious & Private 4BR Retreat - Noted for Cleanliness and Thoughtful Touches
- Hike, Bike & Swim: Mountain Escape w/Deck
- Galloping Getaway on the rolling hills of GemStone Stablen
- Beauty & Charm - The perfect setting for a memorable stay
- Fort Chambers Flat on Main
2. How many vacation rentals have private pools in Greencastle?
There are 16 vacation rentals with private pools near Greencastle. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Greencastle are best for families?
If you are looking for a family-friendly vacation home in Greencastle, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greencastle:
4. How many Rentbyowner vacation rentals are available in Greencastle?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 277 in the Greencastle area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greencastle.
5. What is the cancellation policy for vacation rentals in Greencastle, Pennsylvania?
Cancellation policies vary by property. You should review the specific listing details or contact the owner directly to understand the terms and any applicable fees related to cancellations.
6. How do I find the best vacation rental deals in Greencastle, Pennsylvania?
To secure the best deals, compare listings based on price, amenities, and reviews. Keep an eye out for special offers or discounts that may be available during your preferred travel dates.
7. Are there specific house rules I should be aware of when booking a vacation rental here?
Each rental property has its own set of house rules which can include pet policies, smoking restrictions, and check-in/check-out procedures. It's important to read these rules carefully in the listing or contact the host if you have questions.
8. What is the process for confirming and paying for my vacation rental in this area?
Once you select a property, you will typically need to follow the booking instructions provided, which may involve submitting a reservation request and completing payment through secure methods outlined in the listing.
9. Can I contact the property owner directly if I have specific questions about my stay?
Yes, most listings provide contact information for the property owner or manager. Reaching out directly can help clarify details about the rental and ensure it meets your needs before booking.
Greencastle Top Rated Vacation Rentals
Other
10.0(131 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£108/Night
7 Nights - £759
House
10.0(25 Reviews)
2 Bedrooms
1 Bath
7 Guests
871 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£131/Night
7 Nights - £916
House
9.8(22 Reviews)
4 Bedrooms
3 Baths
9 Guests
1984 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£304/Night
7 Nights - £2,127
House
9.8(8 Reviews)
3 Bedrooms
2 Baths
8 Guests
1750 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
£155/Night
7 Nights - £1,082
£103/Night
7 Nights - £720
£99/Night
7 Nights - £690
£98/Night
7 Nights - £687
Hotel
9.4(558 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
£103/Night
7 Nights - £717
