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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (32 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
$172 nightly
The price is $191
Oct 18 - Oct 19
Total with taxes and fees
Galloping Getaway on the rolling hills of GemStone Stable
A modern bedroom with a large bed, a view of a forest through floor-to-ceiling windows, and a minimalist design.

2. 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, (28 reviews)
"Great place to unwind and relax."
United States
Candace
$618 nightly
The price is $669
Nov 4 - Nov 5
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
A stone pathway leading to a house with a statue in the foreground.

3. 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
Oct 31 - Nov 1
Total with taxes and fees
Beautiful Mansion in the Country & Wedding Venue
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
10.0 out of 10, Exceptional, (14 reviews)
"Absolutely wonderful place. Very clean and comfortable. Wonderful neighborhood with beautiful scenery."
United States
Brandon P.
$234 nightly
The price is $258
Oct 19 - Oct 20
Total with taxes and fees
Rancher in Mont Alto
A brick building with a wooden door and windows.

5. 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.
$208 nightly
The price is $230
Oct 18 - Oct 19
Total with taxes and fees
The Cutest Loft on Main St!
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.

6. 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.
$219 nightly
The price is $242
Oct 18 - Oct 19
Total with taxes and fees
The Boho Penthouse on Main
A modern living room with a sofa, chairs, a coffee table, and a fireplace.

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.
$242 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
The Study on Main Located on the Square!
A bedroom with a wooden slat headboard, a white bedspread, and two bedside lamps.

8. The Mane & Co - No. 6

The Mane & Co - No. 6
Chambersburg
10.0 out of 10, Exceptional, (2 reviews)
"Nice clean place."
United States
Jeffery M.
$208 nightly
The price is $230
Oct 18 - Oct 19
Total with taxes and fees
The Mane & Co - No. 6
An outdoor seating area with Adirondack chairs and a stone fire pit.

9. The Mane & Co - No. 8

The Mane & Co - No. 8
Chambersburg
8.0 out of 10, Very good, (1 review)
"Tiny bathroom. Cable was not working. Overall good and will use this property again"
United States
Richard M.
$225 nightly
The price is $248
Oct 18 - Oct 19
Total with taxes and fees
The Mane & Co - No. 8
A spacious living room with a wooden ceiling, large windows, a fireplace, and a cozy seating area.

10. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
$401 nightly
The price is $449
Oct 20 - Oct 21
Total with taxes and fees
Large Family Home: 5 Mi to Dtwn Hagerstown!
A cozy lounge area with a stone fireplace, comfortable seating, and a ping pong table.

11. 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.
$248 nightly
The price is $264
Oct 18 - Oct 19
Total with taxes and fees
Inns of Whitetail #209
A modern kitchen with a large island, stainless steel appliances, and a minimalist design.

12. 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.
$616 nightly
The price is $680
Oct 18 - Oct 19
Total with taxes and fees
The 1850 Retreat Chambersburg
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.

13. 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
$185 nightly
The price is $204
Oct 29 - Oct 30
Total with taxes and fees
The Mane & Co - No. 4
A rustic, cylindrical structure with a thatched roof, a small seating area, and a view of the surrounding forest.

14. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
10.0 out of 10, Exceptional, (5 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
$209 nightly
The price is $210
Oct 18 - Oct 19
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
A room with large windows, wooden floors, and a ceiling fan.

15. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
$313 nightly
The price is $332
Oct 18 - Oct 19
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A living room with a sofa, a coffee table, a lamp, and a floor lamp.

16. Pine Grove Cottage, quiet and peaceful!

Pine Grove Cottage, quiet and peaceful!
Chambersburg
9.4 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay! Always a great spot to make family memories! "
United States
Kim B.
$504 nightly
The price is $556
Oct 26 - Oct 27
Total with taxes and fees
Pine Grove Cottage, quiet and peaceful!
A house with a covered porch, two wicker chairs, a welcome sign, and a hanging flower basket.

17. 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, (20 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
$167 nightly
The price is $185
Oct 19 - Oct 20
Total with taxes and fees
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
A playground with swings, a slide, and a fire pit area with chairs.

18. 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.
$445 nightly
The price is $495
Oct 18 - Oct 19
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
A hotel room with two beds, a small bathroom, and a window.

19. Spacious 2-Bed Queen | Free Parking

Spacious 2-Bed Queen | Free Parking
Hagerstown
10.0 out of 10, Exceptional, (2 reviews)
"Quiet place with comfy beds. Not too fancy but better than some cheaper options nearby."
United States
Anonymous traveler
$64 nightly
The price is $71
Nov 1 - Nov 2
Total with taxes and fees
Spacious 2-Bed Queen | Free Parking
A living room with a stone fireplace, a sofa, a chair, and a coffee table.

20. Relaxing Countryside Stay w/ Game Room

Relaxing Countryside Stay w/ Game Room
St Thomas
9.4 out of 10, Exceptional, (17 reviews)
"This was a great place to stay"
United States
Christopher D.
$450 nightly
The price is $497
Oct 19 - Oct 20
Total with taxes and fees
Relaxing Countryside Stay w/ Game Room
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

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

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

10/10 Excellent
"Excellent"
Kevin 2-night trip
Posted 7 hours ago
Mirror Villas - Modern Retreat with private hot tubs and mountain view

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 $153 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.