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Compare 139 Vacation Homes in Greencastle with updated reviews, rates, and availability.

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Bender family home, 3 generations of canal boat captains and a Civil War veteran
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
9.6 out of 10, Exceptional, (170)
"Spent two nights at this charming historic home. Check in was easy, home was clean and everything was well explained. Close to Antietam"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
*In The Heart Of Antietam*
Exterior detail
*In The Heart Of Antietam*
9.6 out of 10, Exceptional, (76)
"This was a great historic house to stay in. All modern conveniences while staying true to the structure and history of the home and area. We enjoyed our days visiting Antietam Battle Field, Sharpsburg, and surrounding towns. Beautiful area with lots to see and very friendly people. It was nice to come back at the end of the day and relax in the house with plenty of room unlike a hotel room. Price was great also. "
*In The Heart Of Antietam*
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park
Indoor Salt Pool
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park
10.0 out of 10, Exceptional, (25)
"Our family met here for a weekend getaway. The house is amazing and is stocked with everything you need! The pool room is great, the patio out back has firepits for you to sit around at night, and the kids enjoyed riding their bikes on the property and at the park. The views are beautiful and the beds were comfortable.We brought most of our food with us, but there are stores about 15 minutes away. Its a perfect spot to unplug and relax. "
The price is AED 1,653
AED 3,148 total
includes taxes & fees
6 Nov - 7 Nov
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park
Modern Spacious House With Spectacular Views
Orchard Hill House
Modern Spacious House With Spectacular Views
10.0 out of 10, Exceptional, (58)
"My husband and I enjoyed our visit to immensely. The neighborhood was quiet and peaceful and the views were very nice from the windows. I felt uncomfortable sitting on the large deck with rocking chairs because another house is located directly in front of this side of the rental property. I was not able to tell from the VRBO pictures of this situation prior to renting. Seeing only mountains gave me the impressions this rental was more secluded. Still, a very nice rental and I would come back...
Modern Spacious House With Spectacular Views
SKI YA LATER Whitetail
Welcome to SKI YA LATER Whitetail!
SKI YA LATER Whitetail
9.8 out of 10, Exceptional, (7)
"My family and I Stayed at Ski Ya Later this weekend. Pros: Great location directly next to Whitetail Ski resort and a short drive to the town of Mercersburg. The beds are very comfortable. The place is modern, decorated very nicely. Check in was a breeze. Nice TV, Chargers galore. Spacious- there were four of us (2 adults , 2 teens) but the place can easily sleep up to 8. Cons: We we’re very disappointed with the lack of cleanliness / cleaning service that occurred prior to our visit. I took...
SKI YA LATER Whitetail
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
Living area
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
10.0 out of 10, Exceptional, (1)
"Nice and clean, easy check in and out. The unit was easy to get to, the neighborhood was quiet and it was easy to get to the highway. We were on our way to Ocean City and needed a stop over in MD. This was a pleasant location, easy to get to and perfect for a one night stop over. It was very clean and neat and the off street parking spot was a nice convenience."
The price is AED 367
AED 888 total
includes taxes & fees
10 Nov - 11 Nov
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
Little cute house close to C&O canal
Living room
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 294
AED 584 total
includes taxes & fees
6 Nov - 7 Nov
Little cute house close to C&O canal
Woods Song - Natures Promise
Woods Song - Natures Promise
9.8 out of 10, Exceptional, (31)
"We enjoyed our stay very much. Very cozy cabin, great hot tub!"
Woods Song - Natures Promise
Pine Grove Cottage | 3 Bed, 3 Bath
Interior
Pine Grove Cottage | 3 Bed, 3 Bath
9.2 out of 10, Wonderful, (14)
"Was very nice to see a few staples available upon check in. This made for a much more relaxed atmosphere. Just far enough away from the town to enjoy the quiet, yet close enough to make a short trip to obtain essentials. The only addition we'd recommend is a small fenced in area for little ones. The road behind the house can get busy at times. Would highly recommend for a weekend getaway. Cheers,"
Pine Grove Cottage | 3 Bed, 3 Bath
King Beds with Hot Tub, Arcade Loft & Golf Course View
King Beds with Hot Tub, Arcade Loft & Golf Course View
10.0 out of 10, Exceptional, (6)
"My husband and I stayed at the house and we had a fantastic time. Website description was spit on and the pictures dont do it justice. Thank you Corrine for be such an incredible host. "
The price is AED 566
AED 1,481 total
includes taxes & fees
6 Nov - 7 Nov
King Beds with Hot Tub, Arcade Loft & Golf Course View
2 Storie, Hot Tub, Open Area
2 Storie, Hot Tub, Open Area
7.6 out of 10, Good, (5)
"Beautiful property and neighborhood, very clean and well stocked. Lovely pool, deck and yard. Had a great time with our (adult) kids and grandkids. We're originally from MD and had really missed the mountains! Great communication with the hosts. Very responsive. "
The price is AED 366
AED 1,214 total
includes taxes & fees
17 Nov - 18 Nov
2 Storie, Hot Tub, Open Area
Spacious creekside townhome in the heart of Chambersburg!
Interior
Spacious creekside townhome in the heart of Chambersburg!
10.0 out of 10, Exceptional, (11)
"It was perfect for the vacation "
Spacious creekside townhome in the heart of Chambersburg!
The Garden House
Exterior
The Garden House
10.0 out of 10, Exceptional, (3)
"Beautifully renovated house close to amenities in Chambersburg but nestled away by a farm field and cemetery for privacy. House was clean and the host was quick to respond to messages. Highly recommend this place while staying in Chambersburg."
The Garden House
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Property grounds
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
*Daley's Doll House At Antietam*
HOUSE - front of this cute little one bedroom, one bath dollhouse.
*Daley's Doll House At Antietam*
9.8 out of 10, Exceptional, (92)
"We really enjoyed the property. The home was very cozy and in close proximity to our family in the area. We would definitely stay there again."
*Daley's Doll House At Antietam*
Gettysburg Getaway! Battlefields/Wineries/Ski!
Exterior
Gettysburg Getaway! Battlefields/Wineries/Ski!
9.8 out of 10, Exceptional, (27)
"We brought our grandson with us to visit the Gettysburg sites. That experience was wonderful, but so was having a fishing hole across the street. The house was comfortable and quiet. The countryside was gorgeous on our rides to and from town. Our hosts were very accommodating and friendly. "
Gettysburg Getaway! Battlefields/Wineries/Ski!
Pool, Hot Tub, and Fun for all!
Pool
Pool, Hot Tub, and Fun for all!
10.0 out of 10, Exceptional, (12)
"The host was very attentive and gave great suggestions for things to do in the area based off our interests. The house was clean, and comfortable. Lots of extras to enjoy. "
The price is AED 1,098
AED 1,954 total
includes taxes & fees
11 Nov - 12 Nov
Pool, Hot Tub, and Fun for all!
Historic Chambersburg Home w/ Pool + Game Rooms!
Chambersburg Vacation Rental | 6BR | 5.5BA | 6,200 Sq Ft | Stairs Required
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!
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking
Mercersburg Vacation Rental | 2BR | 1BA | 871 Sq Ft | 2 Steps Required for Entry
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking
10.0 out of 10, Exceptional, (9)
"Clean and welcoming home. No complaints."
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking
Slope View- Great location near the Gettysburg Battlefield and Golf Courses
Outdoor Gas Fire Pit
Slope View- Great location near the Gettysburg Battlefield and Golf Courses
10.0 out of 10, Exceptional, (8)
"Great"
Slope View- Great location near the Gettysburg Battlefield and Golf Courses
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

Traveling to the area for work, we offer discounted rates for long term rentals.
Exterior
Traveling to the area for work, we offer discounted rates for long term rentals.
10.0 out of 10, Exceptional, (13)
"We enjoyed our stay here, the house was very comfortable and well-appointed. We loved the fireplace, the lights on the deck, and were happy it was stocked with games -- we had fun asking each other Trivia questions. We also got to see a deer wander onto the lower part of the property. Would definitely recommend & would stay there again."
The price is AED 331
AED 445 total
includes taxes & fees
10 Nov - 11 Nov
Traveling to the area for work, we offer discounted rates for long term rentals.
Perched in the Trees, Very Private, Screened in Porch with view
Property grounds
Perched in the Trees, Very Private, Screened in Porch with view
10.0 out of 10, Exceptional, (124)
"Giving this 10/10!! Booked as getaway with my husband and I loved it from the moment we arrived. It's nice and cozy, the rocking chairs on the porch makes it even better. Just sitting out there in quiet and listening to mother nature was so relaxing. It pretty much had everything you need and so beautiful inside. The bed was very comfy and it's spacious in the loft area. Very secluded"
The price is AED 404
AED 712 total
includes taxes & fees
6 Nov - 7 Nov
Perched in the Trees, Very Private, Screened in Porch with view
Hidden Gem in the woods with hot tub
Exterior
Hidden Gem in the woods with hot tub
9.4 out of 10, Exceptional, (62)
"The cabin was exceptionally clean and had everything we needed. The location was perfect back in the woods with a nice walk down to the water. "
Hidden Gem in the woods with 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.