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

Greencastle Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Greencastle vacation rentals

Living area

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, (27 reviews)
"We loved staying here. Beautiful views, great communication with Tammie, and very clean. Definitely will stay again!"
United States
Haley H.
$177 nightly
The price is $197
Sep 2 - Sep 3
Total with taxes and fees
Galloping Getaway on the rolling hills of GemStone Stable
Living area

2. Rancher in Mont Alto

Rancher in Mont Alto
Mont Alto
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place. Very clean and comfortable. Wonderful neighborhood with beautiful scenery."
United States
Brandon P.
$216 nightly
The price is $238
Sep 3 - Sep 4
Total with taxes and fees
Rancher in Mont Alto
Room

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
9.8 out of 10, Exceptional, (20 reviews)
"The entire experience was tremendous and the property was very clean. I would highly recommend the experience if you want a beautiful and quiet place to escape to."
United States
Michael
$414 nightly
The price is $443
Sep 2 - Sep 3
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Property grounds

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

Tiny Home with Loft, WI-FI + Free Parking!
Chambersburg
10.0 out of 10, Exceptional, (3 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.
$223 nightly
The price is $246
Sep 2 - Sep 3
Total with taxes and fees
Tiny Home with Loft, WI-FI + Free Parking!
Room

5. 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
$187 nightly
The price is $206
Sep 6 - Sep 7
Total with taxes and fees
The Mane & Co - No. 4
Interior

6. The Boho Penthouse on Main

The Boho Penthouse on Main
Chambersburg
9.4 out of 10, Exceptional, (21 reviews)
"Amazing property , cute downtown, host easy to contact"
United States
Michelle E.
$216 nightly
The price is $238
Sep 2 - Sep 3
Total with taxes and fees
The Boho Penthouse on Main
Private kitchen

7. Fort Chambers Flat on Main

Fort Chambers Flat on Main
Chambersburg
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful and perfect spot to stay! Loved staying close to stores too!"
United States
Christina B.
$291 nightly
The price is $321
Sep 2 - Sep 3
Total with taxes and fees
Fort Chambers Flat on Main
Room

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.
$211 nightly
The price is $233
Sep 2 - Sep 3
Total with taxes and fees
The Mane & Co - No. 6
Living area

9. 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.
$230 nightly
The price is $246
Sep 2 - Sep 3
Total with taxes and fees
Inns of Whitetail #209
Interior

10. 1879 Updated Home on Frederick Street

1879 Updated Home on Frederick Street
Hagerstown
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our stay at this house. It is clean and the beds were very nice. The set up was perfect for us."
United States
Kyle C.
$346 nightly
The price is $364
Sep 2 - Sep 3
Total with taxes and fees
1879 Updated Home on Frederick Street
Exterior detail

11. The Cutest Loft on Main St!

The Cutest Loft on Main St!
Chambersburg
10.0 out of 10, Exceptional, (13 reviews)
"Great stay!"
United States
Kaitlan H.
$211 nightly
The price is $233
Sep 2 - Sep 3
Total with taxes and fees
The Cutest Loft on Main St!
Room

12. 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
Sep 6 - Sep 7
Total with taxes and fees
Cute Place Just Out Of Town With A Country Feel
Interior

13. 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, (4 reviews)
"The house was adorable, the personalized touches, snack basket and welcome note were awesome and made our day. The host was very nice and welcoming. We had a wonderful time."
United States
Bill C.
$220 nightly
The price is $233
Sep 2 - Sep 3
Total with taxes and fees
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Room

14. Lovely, Country Apartment, Just Minutes From Town.

Lovely, Country Apartment, Just Minutes From Town.
Chambersburg
9.8 out of 10, Exceptional, (20 reviews)
"Host was very cordial, amenities were clean and in excellent shape "
United States
Dale B.
$85 nightly
The price is $86
Sep 2 - Sep 3
Total with taxes and fees
Lovely, Country Apartment, Just Minutes From Town.
Exterior detail

15. Bin There Treehouse - A Grain Bin treehouse!

Bin There Treehouse - A Grain Bin treehouse!
Washington County
10.0 out of 10, Exceptional, (3 reviews)
"Such a neat place! Very peaceful setting."
United States
Abby G.
$230 nightly
The price is $232
Sep 3 - Sep 4
Total with taxes and fees
Bin There Treehouse - A Grain Bin treehouse!
Exterior

16. Stone's Throw Bungalow - Cozy and Convenient in Chambersburg, PA

Stone's Throw Bungalow - Cozy and Convenient in Chambersburg, PA
Chambersburg
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay here! Home was just as described & pictured. Response time from host was immediate and we were welcomed with farm fresh eggs and complimentary K-cups. The neighborhood was fabulous for our morning walks too. Would definitely recommend when visiting the area."
United States
Cassie W.
$171 nightly
The price is $189
Sep 9 - Sep 10
Total with taxes and fees
Stone's Throw Bungalow - Cozy and Convenient in Chambersburg, PA
Terrace/patio

17. Air Hill Haven- private peaceful apartment

Air Hill Haven- private peaceful apartment
Chambersburg
10.0 out of 10, Exceptional, (20 reviews)
"The accommodations were wonderful. Highly recommend if you are looking for a place near Shippensburg."
United States
Colleen W.
$128 nightly
The price is $141
Sep 2 - Sep 3
Total with taxes and fees
Air Hill Haven- private peaceful apartment
Living area

18. 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)
"Well fitted out apartment which was larger than the photos showed online. Perfect kitchen (with all the essentials) for a night in, very comfortable bed, and the host was extremely responsive.Easy to follow directions and plenty of Main Street eateries to choose from."
United States
sholto s.
$239 nightly
The price is $264
Sep 2 - Sep 3
Total with taxes and fees
The Study on Main Located on the Square!
Property grounds

19. 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)
$210 nightly
The price is $232
Sep 22 - Sep 23
Total with taxes and fees
Lily Pad - Tiny Home at Mane & Co. / Free Parking
Property grounds

20. 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.
$2,168 nightly
The price is $2,394
Sep 2 - Sep 3
Total with taxes and fees
Beautiful Mansion in the Country & Wedding Venue
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

Hampton Inn Hagerstown-I-81

Hampton Inn Hagerstown-I-81

10/10 Excellent
"Very convenient to Interstate 81. The staff is very pleasant and welcoming. The room was clean, quiet and very comfortable. The breakfast had a very nice selection of eggs, bagels, waffles, yogurt and fresh strawberries and blueberries and more. Patricia (staff) ensured everything was spotless and the guest were satisfied. I would highly recommend this hotel."
Cheryl 1-night trip
Posted less than an hour ago
Hampton Inn Hagerstown-I-81

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 $150 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.