A highway with multiple lanes, surrounded by dense green trees and a distant view of mountains.

Greencastle Vacation Rentals

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Our top choices for Greencastle vacation rentals

1. Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (110 reviews)
"This was our 4th stay and enjoyed every one!"
United States
Anonymous traveller
The price is CA $113
CA $303 total
includes taxes & fees
Nov 12 - Nov 13
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

2. Galloping Getaway on the rolling hills of GemStone Stable

Galloping Getaway on the rolling hills of GemStone Stable
Hagerstown
10.0 out of 10, Exceptional, (33 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
The price is CA $176
CA $258 total
includes taxes & fees
Nov 17 - Nov 18
Galloping Getaway on the rolling hills of GemStone Stable

3. The Mane & Co - No. 4

The Mane & Co - No. 4
Chambersburg
10.0 out of 10, Exceptional, (3 reviews)
"Loved the property & the management was very helpful!"
United States
Tonya
The price is CA $140
CA $276 total
includes taxes & fees
Nov 17 - Nov 18
The Mane & Co - No. 4

4. Lily Pad - Tiny Home at Mane & Co. / Free Parking

Lily Pad - Tiny Home at Mane & Co. / Free Parking
Chambersburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $154
CA $309 total
includes taxes & fees
Nov 11 - Nov 12
Lily Pad - Tiny Home at Mane & Co. / Free Parking

5. Bright 2-Bed ADA Room|Free Parking

Bright 2-Bed ADA Room|Free Parking
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Bed firm yet cozy providing restful support during our stay of one night."
United States
Anonymous traveller
The price is CA $89
CA $100 total
includes taxes & fees
Dec 7 - Dec 8
Bright 2-Bed ADA Room|Free Parking

6. The Cutest Loft on Main St!

The Cutest Loft on Main St!
Chambersburg
9.8 out of 10, Exceptional, (15 reviews)
"Great stay!"
United States
Kaitlan H.
The price is CA $154
CA $309 total
includes taxes & fees
Nov 17 - Nov 18
The Cutest Loft on Main St!

7. The Study on Main Located on the Square!

The Study on Main Located on the Square!
Chambersburg
9.6 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay and the location of the apartment."
United States
Danielle O.
The price is CA $182
CA $364 total
includes taxes & fees
Nov 11 - Nov 12
The Study on Main Located on the Square!

8. Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
Blue Ridge Summit
9.6 out of 10, Exceptional, (21 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
The price is CA $86
CA $239 total
includes taxes & fees
Nov 18 - Nov 19
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.

9. Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
10.0 out of 10, Exceptional, (29 reviews)
"Great place to unwind and relax."
United States
Candace
The price is CA $605
CA $884 total
includes taxes & fees
Nov 17 - Nov 18
Mirror Villas - Modern Retreat with private hot tubs and mountain view

10. Rancher in Mont Alto

Rancher in Mont Alto
Mont Alto
9.8 out of 10, Exceptional, (17 reviews)
"Great place to stay"
United States
Austin B.
The price is CA $178
CA $350 total
includes taxes & fees
Nov 11 - Nov 12
Rancher in Mont Alto

11. The Boho Penthouse on Main

The Boho Penthouse on Main
Chambersburg
9.4 out of 10, Exceptional, (22 reviews)
"Great location to walk to restaurant’s! Apartment was clean and reasonably priced."
United States
Mackenzie B.
The price is CA $154
CA $329 total
includes taxes & fees
Nov 23 - Nov 24
The Boho Penthouse on Main

12. The Mane & Co - No. 5

The Mane & Co - No. 5
Chambersburg
9.4 out of 10, Exceptional, (3 reviews)
"Beautifully modern motel with great amenities and a comfortable bed. The kitchenette was convenient and the bathroom felt luxurious."
United States
Jennifer Z.
The price is CA $140
CA $276 total
includes taxes & fees
Nov 11 - Nov 12
The Mane & Co - No. 5

13. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
9.8 out of 10, Exceptional, (6 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
The price is CA $205
CA $281 total
includes taxes & fees
Nov 11 - Nov 12
Bin There Treehouse - A Grain Bin treehouse!

14. Perched in the Trees, Very Private, Screened in Porch with view

Perched in the Trees, Very Private, Screened in Porch with view
Needmore
9.8 out of 10, Exceptional, (200 reviews)
"Great getaway, clean property, loved the porch."
United States
Martina M.
The price is CA $121
CA $231 total
includes taxes & fees
Nov 19 - Nov 20
Perched in the Trees, Very Private, Screened in Porch with view

15. Beautiful Mansion in the Country & Wedding Venue

Beautiful Mansion in the Country & Wedding Venue
Waynesboro
9.8 out of 10, Exceptional, (9 reviews)
"The stay and place was awesome and my family and I will definitely be booking again "
United States
Comedy C.
The price is CA $1,571
CA $3,372 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful Mansion in the Country & Wedding Venue

16. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is CA $106
CA $216 total
includes taxes & fees
Nov 12 - Nov 13
Bring Your Own Boat - Meticulously restored house on the Potomac River

17. Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (24 reviews)
"Relaxing, close to all."
United States
Valarie
The price is CA $141
CA $533 total
includes taxes & fees
Nov 18 - Nov 19
Peregrine's Perch - Cabin Overlooking the River!

18. Serenity Airstream at Apple Blossom Farm, Hot Tub is Extra

Serenity Airstream at Apple Blossom Farm, Hot Tub is Extra
Orrtanna
10.0 out of 10, Exceptional, (119 reviews)
"Great stay! Thank you!!!"
United States
JULIE M.
The price is CA $134
CA $300 total
includes taxes & fees
Nov 11 - Nov 12
Serenity Airstream at Apple Blossom Farm, Hot Tub is Extra

19. Inns of Whitetail #209

Inns of Whitetail #209
Mercersburg
10.0 out of 10, Exceptional, (3 reviews)
"Great stay for the time we were there, right off the slopes."
United States
Robert M.
The price is CA $244
CA $424 total
includes taxes & fees
Nov 16 - Nov 17
Inns of Whitetail #209

20. Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Hedgesville
9.0 out of 10, Wonderful, (9 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
The price is CA $98
CA $143 total
includes taxes & fees
Nov 11 - Nov 12
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greencastle Hotel Reviews

Find out more about Greencastle

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Greencastle. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Greencastle?

Yes, there are vacation rentals in Greencastle close to Greencastle Coffee Roasters, or you can select a secluded option if you'd like a relaxing place to stay. Our travelers say Greencastle has a good selection of restaurants. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals that Greencastle has to offer?

Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!: This vacation home rental near Greencastle offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Greencastle?

Explore the area and cultural attractions such as Renfrew Museum and Park, or visit a family-friendly sight such as Greencastle Coffee Roasters. Martins Mill Bridge and Pennsylvania Dutch Market are a couple of places you'll find in the larger area.

What are vacation rentals like in Greencastle?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Greencastle. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.