A town street with cars parked on both sides, a church steeple in the distance, and a roundabout with street lamps.

Greencastle Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (31 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
$171 nightly
The price is $190
Oct 6 - Oct 7
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, (26 reviews)
"Great place to unwind and relax."
United States
Candace
$637 nightly
The price is $691
Nov 4 - Nov 5
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.

3. Rancher in Mont Alto

Rancher in Mont Alto
Mont Alto
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place. Very clean and comfortable. Wonderful neighborhood with beautiful scenery."
United States
Brandon P.
$215 nightly
The price is $237
Oct 6 - Oct 7
Total with taxes and fees
Rancher in Mont Alto
A stone pathway leading to a house with a statue in the foreground.

4. 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.
$2,148 nightly
The price is $2,371
Oct 24 - Oct 25
Total with taxes and fees
Beautiful Mansion in the Country & Wedding Venue
A brick building with a wooden door and windows.

5. The Cutest Loft on Main St!

The Cutest Loft on Main St!
Chambersburg
10.0 out of 10, Exceptional, (14 reviews)
"Great stay!"
United States
Kaitlan H.
$208 nightly
The price is $230
Oct 6 - Oct 7
Total with taxes and fees
The Cutest Loft on Main St!
A bedroom with a bed, a ceiling fan, a bedside table, a nightstand, a small plant, and a wall-mounted shelf.

6. Cute Place Just Out Of Town With A Country Feel

Cute Place Just Out Of Town With A Country Feel
Chambersburg
10.0 out of 10, Exceptional, (48 reviews)
"Our favorite place to stay!"
United States
Melissa H.
$82 nightly
The price is $83
Oct 6 - Oct 7
Total with taxes and fees
Cute Place Just Out Of Town With A Country Feel
Two Adirondack chairs with a black metal fire pit in between, set on a stone patio with a grassy area and trees in the background.

7. Tiny Home with Loft, WI-FI + Free Parking!

Tiny Home with Loft, WI-FI + Free Parking!
Chambersburg
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly room was really clean and tastefully decorated. The location is great and the outside firepit was cool - enjoyed seeing it even though we didnt advantage of it since our stay was short. "
United States
Beth W.
$222 nightly
The price is $245
Oct 12 - Oct 13
Total with taxes and fees
Tiny Home with Loft, WI-FI + Free Parking!
A living room with a sofa, a coffee table, a lamp, and a floor lamp.

8. 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.
$465 nightly
The price is $514
Oct 6 - Oct 7
Total with taxes and fees
Pine Grove Cottage, quiet and peaceful!
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.

9. The Boho Penthouse on Main

The Boho Penthouse on Main
Chambersburg
9.4 out of 10, Exceptional, (22 reviews)
"Amazing property , cute downtown, host easy to contact"
United States
Michelle E.
$213 nightly
The price is $235
Oct 6 - Oct 7
Total with taxes and fees
The Boho Penthouse on Main
A building with a red brick pathway leading to a white metal fence.

10. Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D

Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D
Hagerstown
10.0 out of 10, Exceptional, (3 reviews)
"Carrie was very responsive and helpful. The location is as advertised. Would stay again for sure."
United States
Mark P.
$291 nightly
The price is $308
Oct 30 - Oct 31
Total with taxes and fees
Luxurious large condo, no steps,amenities galore. Brand new, Secure, Parking,W/D
A modern living room with a sofa, chairs, a coffee table, and a fireplace.

11. The Study on Main Located on the Square!

The Study on Main Located on the Square!
Chambersburg
9.6 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay and the location of the apartment."
United States
Danielle O.
$236 nightly
The price is $261
Oct 6 - Oct 7
Total with taxes and fees
The Study on Main Located on the Square!
A spacious living area with a large window, a wooden ceiling, and a dining area with a table and chairs.

12. 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
$324 nightly
The price is $361
Oct 7 - Oct 8
Total with taxes and fees
Peregrine's Perch - Cabin Overlooking the River!
A cozy lounge area with a stone fireplace, comfortable seating, and a ping pong table.

13. 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.
$246 nightly
The price is $262
Oct 6 - Oct 7
Total with taxes and fees
Inns of Whitetail #209
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

14. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (6 reviews)
$214 nightly
The price is $227
Oct 19 - Oct 20
Total with taxes and fees
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A house with a covered porch, two wicker chairs, a welcome sign, and a hanging flower basket.

15. 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, (19 reviews)
"Great spot close to the wedding venue!!"
United States
Alfred T.
$168 nightly
The price is $186
Oct 13 - Oct 14
Total with taxes and fees
Charming Mountain Top Suite. Minutes from Ski Liberty and Gettysburg.
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.

16. 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 kitchen with white cabinets, a granite countertop, a stainless steel sink, a stove, and a window with a view of trees.

17. 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.
$140 nightly
The price is $141
Oct 6 - Oct 7
Total with taxes and fees
Sunsets With a Country View
A bedroom with a wooden slat headboard, a white bedspread, and two bedside lamps.

18. 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 8 - Oct 9
Total with taxes and fees
The Mane & Co - No. 6
A room with large windows, wooden floors, and a ceiling fan.

19. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a great stay! Everything was clean & well organized. The house was well stocked with everything we need. We would definitely stay here again."
United States
Stephen V.
$310 nightly
The price is $329
Oct 6 - Oct 7
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A hot tub with a waterfall feature, surrounded by a wooden deck and lush greenery.

20. Apple Blossom Cottage Of Gettysburg. Hot Tub is an Add on Fee

Apple Blossom Cottage Of Gettysburg. Hot Tub is an Add on Fee
Orrtanna
9.8 out of 10, Exceptional, (346 reviews)
"Everything was perfect, great peaceful stay "
United States
Tony K.
$219 nightly
The price is $242
Oct 7 - Oct 8
Total with taxes and fees
Apple Blossom Cottage Of Gettysburg. Hot Tub is an Add on Fee
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

Country Inn & Suites by Radisson, Chambersburg, PA

Country Inn & Suites by Radisson, Chambersburg, PA

8/10 Good
"Hot tub permanently closed, pool look to have a film on it didnt even bother to go in. Not much breakfast options when went at 8am. Room was clean and bed comfortable."
Erin 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Chambersburg, PA

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 $164 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.