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

Greencastle Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Greencastle vacation rentals

A living room with a sofa, a TV mounted on the wall, and a large sliding glass door leading to a garden.

1. 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.
$164 nightly
The price is $183
Nov 6 - Nov 7
Total with taxes and fees
Galloping Getaway on the rolling hills of GemStone Stable
A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

2. 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 traveler
$220 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A modern bedroom with a large bed, a view of a forest through floor-to-ceiling windows, and a minimalist design.

3. 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
$607 nightly
The price is $657
Nov 29 - Nov 30
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
A cozy room with a grey sofa, a small bedside table with a lamp, and a window with curtains.

4. 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.
$222 nightly
The price is $246
Nov 9 - Nov 10
Total with taxes and fees
Rancher in Mont Alto
A fire pit area with Adirondack chairs and a stone fire pit labeled "Mane & Co."

5. The Nomad - Tiny Home at Mane + Co. with King Bed

The Nomad - Tiny Home at Mane + Co. with King Bed
Chambersburg
$210 nightly
The price is $232
Nov 8 - Nov 9
Total with taxes and fees
The Nomad - Tiny Home at Mane + Co. with King Bed
A bedroom with a wooden slat headboard, two bedside lamps, a bed with a white comforter and two pink pillows, a beige throw blanket, and a wall-mounted coat rack.

6. 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
$177 nightly
The price is $196
Nov 8 - Nov 9
Total with taxes and fees
The Mane & Co - No. 4
A cozy lounge area with a stone fireplace, comfortable seating, and a ping pong table.

7. 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.
$235 nightly
The price is $251
Nov 6 - Nov 7
Total with taxes and fees
Inns of Whitetail #209
A spacious living room with a brick wall, a flat-screen TV, a large window, and a cozy seating area with a round table and chairs.

8. 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.
$201 nightly
The price is $223
Nov 22 - Nov 23
Total with taxes and fees
The Boho Penthouse on Main
A modern living room with a sofa, chairs, a coffee table, and a fireplace.

9. 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.
$231 nightly
The price is $256
Nov 9 - Nov 10
Total with taxes and fees
The Study on Main Located on the Square!
A brick building with a wooden door and windows.

10. 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.
$199 nightly
The price is $220
Nov 8 - Nov 9
Total with taxes and fees
The Cutest Loft on Main St!
A hallway with a black mat leading to a kitchenette area, a refrigerator, and a television on a wooden shelf.

11. Spacious King Bed | Free Parking

Spacious King Bed | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Checking in took no time, plus blackout curtains provided just the right setting for sleeping soundly at night."
United States
Anonymous traveler
$71 nightly
The price is $80
Dec 1 - Dec 2
Total with taxes and fees
Spacious King Bed | Free Parking
A house with a covered porch, two wicker chairs, a welcome sign, and a hanging flower basket.

12. 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)
"The host is super friendly and responsive. The unit is very clean and worked great for our needs. The location is close to Gettysburg, but allowed us to get out of town a bit, and into the beautiful countryside."
United States
Jeff D.
$164 nightly
The price is $182
Nov 8 - Nov 9
Total with taxes and fees
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
A modern kitchen with a black backsplash, wooden shelves, and a coffee maker.

13. 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.
$177 nightly
The price is $196
Nov 8 - Nov 9
Total with taxes and fees
The Mane & Co - No. 5
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

14. 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.
$137 nightly
The price is $153
Nov 6 - Nov 7
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

15. 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.
$217 nightly
The price is $218
Nov 10 - Nov 11
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a stove, and a window with a view of trees.

16. Sunsets With a Country View

Sunsets With a Country View
Chambersburg
9.8 out of 10, Exceptional, (27 reviews)
"House was very comfy! Definitely felt like a home away from home. Would definitely like to stay again! "
United States
Jessica W.
$137 nightly
The price is $138
Nov 6 - Nov 7
Total with taxes and fees
Sunsets With a Country View
A stone pathway leading to a house with a statue in the foreground.

17. 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.
$2,149 nightly
The price is $2,372
Nov 6 - Nov 7
Total with taxes and fees
Beautiful Mansion in the Country & Wedding Venue
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

18. 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
$336 nightly
The price is $374
Nov 9 - Nov 10
Total with taxes and fees
Peregrine's Perch - Cabin Overlooking the River!
A modern kitchen with a large island, stainless steel appliances, and a minimalist design.

19. The 1850 Retreat Chambersburg

The 1850 Retreat Chambersburg
Chambersburg
10.0 out of 10, Exceptional, (12 reviews)
"We really enjoyed our stay. The house was beautiful and they were very responsive to our questions. "
United States
Lee S.
$585 nightly
The price is $647
Nov 9 - Nov 10
Total with taxes and fees
The 1850 Retreat Chambersburg
A playground with swings, a slide, and a fire pit area with chairs.

20. Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Welcoming and spacious for all invitees and we did not even have a chance to explore all the areas that were surrounding as it was a work related trip but will get out there at some later point for a completely relaxing stay for sure"
United States
Image M.
$422 nightly
The price is $471
Nov 8 - Nov 9
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greencastle Hotel Reviews

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

8/10 Good
"everything was great !!!!"
michelle 1-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Find out more about Greencastle

Everything you need to know about Greencastle vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greencastle vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greencastle vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greencastle vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greencastle. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greencastle in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $137 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greencastle rentals

At Expedia, we put the best Greencastle vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greencastle rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greencastle vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greencastle. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.