Search Vacation Homes in Greencastle

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Our top choices for Greencastle vacation homes

Vacation Home in Berkeley Springs

Modern, family-friendly, nature packed getaway
9.2 out of 10, Wonderful, (19)
"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "
United States
Erika R.
$243 nightly
The price is $271
Dec 23 - Dec 24
Total with taxes and fees
Modern, family-friendly, nature packed getaway

Vacation Home in Hagerstown

1879 Updated Home on Frederick Street
9.0 out of 10, Wonderful, (4)
"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.
$349 nightly
The price is $368
Dec 23 - Dec 24
Total with taxes and fees
1879 Updated Home on Frederick Street
6.0 out of 10, (1)
"The inside was very clean, outside was a mess. Location was bad, on a busy street and a busy railway."
United States
mark C.
$202 nightly
The price is $214
Dec 23 - Dec 24
Total with taxes and fees
3-bedroom townhome in charming Hagerstown with AC, WiFi
8.6 out of 10, Excellent, (10)
"We had an amazing stay at your cabin! It was just what we were hoping for. The neighborhood is nicely spread out, giving the kids lots of space to roam and explore. The beds were super comfortable, and the kitchen had everything we needed to cook our meals. Communication with the host was excellent, and we really appreciated the guest passes to the sports center. We’d love to return again soon!"
United States
Jamie W.
$322 nightly
The price is $349
Jan 20 - Jan 21, 2026
Total with taxes and fees
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
9.8 out of 10, Exceptional, (54)
"Very nice stay. Close to everything and great amenities. Will definitely stay again if we are back in the area"
United States
Cammeron F.
$328 nightly
The price is $362
Jan 4 - Jan 5, 2026
Total with taxes and fees
The General's Hideaway near Gettysburg Battlefields, Wineries, Skiing & Hiking less than a mile from the Cashtown Inn
9.8 out of 10, Exceptional, (9)
"The stay and place was awesome and my family and I will definitely be booking again "
United States
Comedy C.
$2,478 nightly
The price is $2,736
Dec 23 - Dec 24
Total with taxes and fees
Beautiful Mansion in the Country & Wedding Venue
9.4 out of 10, Exceptional, (110)
"Alot of choices for food and snacks within walking distance. "
United States
Cherilyn H.
$278 nightly
The price is $295
Dec 30 - Dec 31
Total with taxes and fees
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
9.4 out of 10, Exceptional, (22)
"Beautiful place! Clean and easy check in "
United States
Logan H.
$243 nightly
The price is $258
Dec 23 - Dec 24
Total with taxes and fees
Renovated Farmhouse located near the C and O Canal
10.0 out of 10, Exceptional, (23)
"Easy, pleasant stay "
United States
Mike H.
$395 nightly
The price is $419
Dec 29 - Dec 30
Total with taxes and fees
Nice and modern decor, 4BR 3BA, remodeled
9.8 out of 10, Exceptional, (49)
"Very nice home. Cozy and comfortable ."
United States
Angel C.
$416 nightly
The price is $459
Dec 29 - Dec 30
Total with taxes and fees
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Vacation Home in Mercersburg

Inns Unit 108 Summary
6.0 out of 10, (2)
"Absolutely amazing ! Very clean and Check in was super easy . "
United States
Tiffany B.
$269 nightly
The price is $289
Dec 23 - Dec 24
Total with taxes and fees
Inns Unit 108 Summary
10.0 out of 10, Exceptional, (10)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
$507 nightly
The price is $552
Jan 20 - Jan 21, 2026
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
10.0 out of 10, Exceptional, (38)
"We enjoyed staying here, everything was nice."
United States
Yuriy N.
$1,154 nightly
The price is $1,248
Dec 29 - Dec 30
Total with taxes and fees
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park
9.4 out of 10, Exceptional, (15)
"Over all stay was excellent. House was very nice with floor to ceiling windows. Also there was a hot tub and acade game room. Beautiful location over looking golf course. "
United States
Jeffrey H.
$430 nightly
The price is $467
Jan 8 - Jan 9, 2026
Total with taxes and fees
King Beds with Hot Tub, Arcade & Golf Course View
$240 nightly
The price is $265
Dec 29 - Dec 30
Total with taxes and fees
Charming getaway, sleeps 9, easy access, 8 miles to battlefields, pet friendly.
9.6 out of 10, Exceptional, (31)
"The owners of this property truly made us feel at home. This is a beautiful and spacious property that is centrally located. Extremely comfortable and well decorated. I would highly recommend it! "
United States
Maria Q.
$651 nightly
The price is $719
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Freckled Farmhouse near Gettysburg Battlefields, Wineries, Skiing, & Hiking Sleeps 14

Vacation Home in Chambersburg

The 1850 Retreat Chambersburg
10.0 out of 10, Exceptional, (8)
"Beautiful place, great for a couple of families. Love all the added touches and kitchen. The host got back to me very quickly with any issues. Would stay there again in a heartbeat!"
United States
Wendi S.
$590 nightly
The price is $651
Jan 4 - Jan 5, 2026
Total with taxes and fees
The 1850 Retreat Chambersburg
5.0 out of 10, (2)
"This is an older home in Hagerstown but it is right across from the the new minor league baseball stadium. It is walking distance to restaurants and sites downtown. We really enjoyed all the 90's memorabilia and watched VHS tapes and played games in the evening"
United States
A K.
$277 nightly
The price is $294
Dec 23 - Dec 24
Total with taxes and fees
Step in the 90's in Historic Downtown Hagerstown
2.0 star property
$320 nightly
The price is $346
Jan 19 - Jan 20, 2026
Total with taxes and fees
Modern w/ Hot Tub, Grill, WiFi & Resort Access
$570 nightly
The price is $623
Dec 24 - Dec 25
Total with taxes and fees
Amazing Views, Fireplace, Grill, & Resort Access!
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

Find out more about Greencastle

Greencastle Vacation Homes information

Number of reviews
390
Accommodation
144 Vacation Homes
Lowest Price
$214
Highest Price
$2,736

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