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Compare 142 Vacation Homes in Greencastle with updated reviews, rates, and availability.

Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

10.0 out of 10, Exceptional, (13)
"We stayed here with two adults and three kids. Easy proximity to Whitetail. The place is exactly as advertised and host was responsive and helpful"
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

*In The Heart Of Antietam*

9.6 out of 10, Exceptional, (81)
"House is clean, pleasant with comfortable beds, a serviceable kitchen and nice common space. My husband and 2 adult children were visiting family who live in sharpsburg and their house was pretty full with other visitors. This was a perfect place for us. Highly recommend. "
*In The Heart Of Antietam*

The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing, & Hiking

9.8 out of 10, Exceptional, (47)
"This was just as described! The location was perfect for Gettysburg and Maryland. We were able to go exploring and make a short trip back to relax."
The price is AED 569
AED 1,228 total
includes taxes & fees
9 Feb - 10 Feb
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing, & Hiking

Gettysburg Getaway! Battlefields/Wineries/Ski!

9.8 out of 10, Exceptional, (30)
"This area is quiet and close to Gettysburg. The house is very nice and roomy. I would recommend staying at this property."
Gettysburg Getaway! Battlefields/Wineries/Ski!

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

10.0 out of 10, Exceptional, (27)
"Beautiful house, wonderful kitchen and dining room. TVs everywhere. Game room. And of course the heated indoor pool. Spent Thanksgiving there. Saw deer outside each morning."
The price is AED 1,653
AED 3,148 total
includes taxes & fees
4 Feb - 5 Feb
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

7.0 out of 10, Good, (7)
"This property met our needs beautifully. We will stay here again if we come back to the area, for sure"
The price is AED 360
AED 736 total
includes taxes & fees
4 Feb - 5 Feb
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Modern Spacious House With Spectacular Views

10.0 out of 10, Exceptional, (66)
"Our stay was pleasant. The place was roomy and all amenities needed. The views were wonderful. Our only gripe is that the owners live downstairs and you can hear talking, movies/music etc so wouldnt recommend if you are seeking complete privacy. A lady that was looking for a women called Jane actually walked right in to our rented home. We thought that was a bit forward and shocked that she thought it was okay to just walk in without even a knock. But thats not the owners fault, just poor...
Modern Spacious House With Spectacular Views

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

9.8 out of 10, Exceptional, (46)
"We stayed for two nights while introducing our kids to skiing at nearby Liberty resort. We were fortunate to get 6inches of beautiful snow while we were there, and enjoyed tremendously watching it blanket the trees around us Eileen was very helpful and ensured we had snow shovels and salt! Definitely will be back! "
The price is AED 1,469
AED 2,307 total
includes taxes & fees
3 Feb - 4 Feb
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Woods Song - Natures Promise

9.8 out of 10, Exceptional, (35)
"A great relaxing weekend."
Woods Song - Natures Promise

The Peaceful Nest

10.0 out of 10, Exceptional, (1)
"I’ve been a frequent traveler for over 50yrs(25 of which was spent in the military). This weekend I brought my wife, four (of seven) kids and two (of five) grand kids skiing and snow tubing. I’ve camped in this area several times, but we have never tried the slopes before. The entire experience could not have been better. The house was very large and easily accommodated our needs. It was full of all the amenities as listed and was excellently located just minutes from Liberty Mountain Resort. My...
The price is AED 790
AED 1,577 total
includes taxes & fees
3 Feb - 4 Feb
The Peaceful Nest

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.6 out of 10, Exceptional, (175)
"We thoroughly enjoyed our stay at the house. It was very clean and fully provisioned. It was really great to stay in such a cool period structure, particularly one that is in such great shape and includes all manner of modern conveniences! The hosts were very welcoming and responsive to questions. Bravo!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Lake House w/ Pool and King Bed, Fishing - Dogs OK

9.4 out of 10, Exceptional, (20)
"The water quality was my only complaint. It was extra hard."
Lake House w/ Pool and King Bed, Fishing - Dogs OK

Historic Chambersburg Home w/ Pool + Game Rooms!

10.0 out of 10, Exceptional, (5)
"We stayed here while in town for a wedding. We had 13 adults and one child. This is such a neat old house with so many cool features. We had a fun time exploring the house and admiring the unique features like the Jefferson doors to the porches, the old coal dump, and all the super cool antiques in the home. All of the bedrooms have a sink in them which was really awesome and helpful for when we were all getting ready at the same time. Our only feedback is that the pillows were a little hard and...
Historic Chambersburg Home w/ Pool + Game Rooms!

Slope View- Great location near the Gettysburg Battlefield and Golf Courses

10.0 out of 10, Exceptional, (10)
"Our family of 5 stayed here for our ski trip at Liberty Mountain. Tasha was friendly and responsive. The home was clean and beds were comfortable. Just what we needed!"
Slope View- Great location near the Gettysburg Battlefield and Golf Courses

Visit our charming cottage this Spring. Enjoy the blooming flowers and scenery.

9.8 out of 10, Exceptional, (37)
"Felt right at home staying here. A short drive to Gettysburg. Would definitely stay here and and will be recommending it to friends. "
Visit our charming cottage this Spring. Enjoy the blooming flowers and scenery.

Cabin at Sleepy Creek - Charming Cabin

9.6 out of 10, Exceptional, (37)
"This was our second visit to the cabin and we loved it! The back screened in porch is perfect for sitting and relaxing. The location is great if you are seeking relaxation, there are other cabins nearby but it was very quiet. The cabin was very clean when we arrived. We will be back!"
Cabin at Sleepy Creek - Charming Cabin

Dog Friendly - Minutes to Liberty Mtn & Gettysburg

10.0 out of 10, Exceptional, (29)
"My family had so much fun it was the perfect house and she really thought of everything we could have needed or forgot! "
The price is AED 984
AED 1,938 total
includes taxes & fees
10 Feb - 11 Feb
Dog Friendly - Minutes to Liberty Mtn & Gettysburg

Mountain view, rural and cozy.

10.0 out of 10, Exceptional, (6)
"Perfect location to get together with sisters to bake and be kids again. The kitchen was very accommodating for the 4 of us to bake Christmas goodies and not step on each other. "
Mountain view, rural and cozy.

Pine Grove Cottage | 3 Bed, 3 Bath

9.2 out of 10, Wonderful, (15)
"This property was comfortable with lots of little extras to make the stay pleasant. The location was a quick drive to Chambersburg to grab some groceries/carry out or to walk the rail trail. Or you can drive a little further to Shippensburg or Caledonia. The kitchen was well equipped, the oven and stove worked well, and we found some basics in the pantry...plus some extras like a great pancake mix! We found the two larger beds to be comfortable and there are lots of blankets to choose from to...
Pine Grove Cottage | 3 Bed, 3 Bath

Little cute house close to C&O canal

8.4 out of 10, Very Good, (6)
"We helped the owner resolve the double booking. I only wish he had taken responsibility for the mistake and not blamed the app. I am grateful for the other travelers who gave up their reservation and went looking for somewhere else to stay."
The price is AED 257
AED 545 total
includes taxes & fees
7 Feb - 8 Feb
Little cute house close to C&O canal
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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Other property types in Greencastle

The SKI SLOPES are open and we are only minutes away. Book your stay now!!!

10.0 out of 10, Exceptional, (19)
"This is our second time at this property. It’s about 20 minutes from Whitetail Resort. It was a great place to wind down after a day of skiing. Spacious and comfortable. Because of heavy snowfall in the afternoon, there was about 4 inches or more of snow in the driveway and my car got stuck. I went up the wrong driveway, but in any case both driveways were snow covered and impassible unless you had chains. Even with four-wheel-drive our wheels were spinning. Had to leave the car parked in the...
The price is AED 364
AED 481 total
includes taxes & fees
3 Feb - 4 Feb
The SKI SLOPES are open and we are only minutes away. Book your stay now!!!

Perched in the Trees, Very Private, Screened in Porch with view

10.0 out of 10, Exceptional, (132)
"This place was an amazing experience. The view was awesome in the morning. Very cool place and the host were easy to work with. "
The price is AED 349
AED 642 total
includes taxes & fees
6 Feb - 7 Feb
Perched in the Trees, Very Private, Screened in Porch with view

Waterfront Cabin overlooking the Potomac River W/ Hot Tub

9.8 out of 10, Exceptional, (51)
"We really enjoyed our stay at this property, where we nestled down for winter cooking, movies, and excellent snowy hot tub time watching the frozen Potomac. Its close enough for an excursion to Berkeley Springs, and we liked the bed! I often find rental mattresses to be too hard and this one was just right."
The price is AED 514
AED 1,014 total
includes taxes & fees
3 Feb - 4 Feb
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
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.