Greencastle Vacation Rentals

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Our top choices for Greencastle vacation homes

1. 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 17 - Nov 18
Rancher in Mont Alto

2. 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 13 - Nov 14
Beautiful Mansion in the Country & Wedding Venue

3. 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.
The price is CA $454
CA $701 total
includes taxes & fees
Nov 12 - Nov 13
Pine Grove Cottage, quiet and peaceful!

4. Relaxing Countryside Stay w/ Game Room

Relaxing Countryside Stay w/ Game Room
St Thomas
9.4 out of 10, Exceptional, (17 reviews)
"Great location nice and quiet. Would stay again"
United States
Debra R.
The price is CA $384
CA $674 total
includes taxes & fees
Nov 12 - Nov 13
Relaxing Countryside Stay w/ Game Room

5. Inns of Whitetail #108

Inns of Whitetail #108
Mercersburg
6.0 out of 10, (2 reviews)
"Absolutely amazing ! Very clean and Check in was super easy . "
United States
Tiffany B.
The price is CA $220
CA $397 total
includes taxes & fees
Nov 12 - Nov 13
Inns of Whitetail #108

6. 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, (11 reviews)
"I cannot say enough about the wonderful time we had staying at Denise & Mike's lovely cottage. They went above and beyond to make sure our family gathering was perfect...and it truly was. Sitting on the front porch sharing coffee in the a.m. and wine in the evening. Board games, chats and laughter until our bellies ached. Our family spent our much needed reunion sharing long overdue times making more wonderful memories. Upon arrival we found the property even more special than we imagined from...
United States
Julianne L.
The price is CA $164
CA $350 total
includes taxes & fees
Nov 22 - Nov 23
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

7. 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.
The price is CA $479
CA $914 total
includes taxes & fees
Nov 12 - Nov 13
The 1850 Retreat Chambersburg

8. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (19 reviews)
"Cute place with a lot of character. Host was very responsive. We enjoyed our sray."
United States
Dawn V.
The price is CA $211
CA $451 total
includes taxes & fees
Nov 12 - Nov 13
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

9. Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!
Orrtanna
10.0 out of 10, Exceptional, (121 reviews)
"Beautiful, quiet property, and the hosts were great to work with!"
United States
Matthew L.
The price is CA $158
CA $193 total
includes taxes & fees
Nov 24 - Nov 25
Cozy and Clean Farmhouse in Mountains near Gettysburg. No extra cleaning fees!

10. The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn
Orrtanna
9.8 out of 10, Exceptional, (61 reviews)
"Our host was prompt on questions and the house was clean and cute. Our family was able to relax and enjoy the property while on vacation"
United States
Ash Lee S.
The price is CA $242
CA $476 total
includes taxes & fees
Nov 19 - Nov 20
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn

11. Relax near Gettysburg ski/wineries/fire pit!

Relax near Gettysburg ski/wineries/fire pit!
Orrtanna
10.0 out of 10, Exceptional, (54 reviews)
"Wonderful property, very cozy!"
United States
Lisa G.
The price is CA $353
CA $655 total
includes taxes & fees
Nov 15 - Nov 16
Relax near Gettysburg ski/wineries/fire pit!

12. Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6
Orrtanna
9.8 out of 10, Exceptional, (18 reviews)
"Just perfect, love this place definitely coming back when I stay in Pennsylvania"
United States
William G.
The price is CA $217
CA $430 total
includes taxes & fees
Nov 15 - Nov 16
Rested Rooster Maisonette! Near Gettysburg and Cashtown Inn Sleeps 6

13. Whispering Pines Cabin Cozy Forest Cabin Retreat

Whispering Pines Cabin Cozy Forest Cabin Retreat
Biglerville
10.0 out of 10, Exceptional, (10 reviews)
"We had an amazing time and the owners were so nice ! We will definitely be back !"
United States
Melissa G.
The price is CA $435
CA $803 total
includes taxes & fees
Nov 24 - Nov 25
Whispering Pines Cabin Cozy Forest Cabin Retreat

14. Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (52 reviews)
"Awesome place."
United States
Holly J.
The price is CA $565
CA $845 total
includes taxes & fees
Nov 12 - Nov 13
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

15. Mountain retreat w/deck, game room & dog-friendly

Mountain retreat w/deck, game room & dog-friendly
The Woods
9.2 out of 10, Wonderful, (7 reviews)
"This property was exactly as advertised and our family had a great time. It was one of the cleanest homes we have stayed at and Tony and his crew responded quickly to any minor needs we had. It is very easy to highly recommend this home."
United States
Roy N.
The price is CA $261
CA $801 total
includes taxes & fees
Nov 18 - Nov 19
Mountain retreat w/deck, game room & dog-friendly

16. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.2 out of 10, Very good, (66 reviews)
"I was surprised to see how dilapidated the decking around the house was. I was concerned we might trip or fall through. The location was ideal for bicycling and fishing . The backyard was beautiful with the most prettiest flowers and trees."
United States
Susie R.
The price is CA $261
CA $584 total
includes taxes & fees
Nov 15 - Nov 16
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

17. Modern w/ Hot Tub, Grill, WiFi & Resort Access

Modern w/ Hot Tub, Grill, WiFi & Resort Access
The Woods
The price is CA $257
CA $591 total
includes taxes & fees
Nov 16 - Nov 17
Modern w/ Hot Tub, Grill, WiFi & Resort Access

18. Private Hillside Retreat w/ Hot Tub Near Gettysburg

Private Hillside Retreat w/ Hot Tub Near Gettysburg
Orrtanna
9.0 out of 10, Wonderful, (11 reviews)
"This property is in an absolutely stunning location. The view from the front porch is breathtaking. The house is impeccably decorated and extremely clean. The property is also centrally located to many local attractions. I would highly recommend this property to others."
United States
Maria Q.
The price is CA $543
CA $990 total
includes taxes & fees
Nov 12 - Nov 13
Private Hillside Retreat w/ Hot Tub Near Gettysburg

19. The Woods Resort w/ Jacuzzi, 2 Decks +Fireplace

The Woods Resort w/ Jacuzzi, 2 Decks +Fireplace
The Woods
The price is CA $204
CA $494 total
includes taxes & fees
Nov 12 - Nov 13
The Woods Resort w/ Jacuzzi, 2 Decks +Fireplace

20. Gorgeous Vacation Rental with Grill, Fire Pit, Golf Course Views, and Resort Access in Hedgesville, West Virginia

Gorgeous Vacation Rental with Grill, Fire Pit, Golf Course Views, and Resort Access in Hedgesville, West Virginia
The Woods
The price is CA $726
CA $879 total
includes taxes & fees
Nov 12 - Nov 13
Gorgeous Vacation Rental with Grill, Fire Pit, Golf Course Views, and Resort Access in Hedgesville, West Virginia
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.

Learn more about Greencastle

Discover local history at Allison-Antrim Museum, where artifacts and exhibits tell the story of this charming small town. Enjoy outdoor recreation at Jerome R. King Playground or attend community events at the Greencastle-Antrim Chamber of Commerce during summer festivals.

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

Top reviews in Greencastle

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