Vacation rentals in Greencastle

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Top-rated holiday rentals in Greencastle

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Greencastle
Country 2-Bed/2-Bath Apartment with Beautiful View
Rural agricultural setting but convenient to towns, golfing, Whitetail Ski Resort and civil war historical sites. Two bedrooms with queen beds w/linens, two full baths, full kitchen living room area, desk and outdoor firepit and chairs (firewood for additional fee). Queen pull-out sofa bed. Wi-Fi and HDTV. Paved drive/parking area. Pets welcome w/agreement. Short drive to I-81 and I-70 20 mins to Hagerstown 15 mins to Chambersburg 20 mins to Whitetail Ski Resort 1.5 hrs to Baltimore/Washington
11 – 18 Feb
4.97 out of 5 average rating, 184 reviews
Guest favourite
Guest suite in Mercersburg
The 1780 Cabin on Main
A charming cabin built circa 1780 situated right on Main Street, just steps from Pubs and Restaurants and easy walking distance to historic Mercersburg Academy. There is a separate sleeping area upstairs with a queen-size memory foam bed. The lower level features a foldout couch and air mattress for additional guests, as well as a 55" TV and a wet bar and bathroom. Visitors have universally enjoyed the cabin's cozy feel. While there is no yard available, the town is great for walking dogs.
20 – 27 Apr
4.94 out of 5 average rating, 396 reviews
Guest favourite
Apartment in Clear Spring
Clean, quiet. Whitetail, I-70/I-81 15 min away!
Come, relax and enjoy your stay in the area with us! The perfect HideAway to hang your hat, let your hair down or to enjoy privacy, peace & quiet while you work online on your laptop. Ski day/evening during the winter or golf during suitable weather at Whitetail. Visit other attractions including National Parks to visit, hike or bike. Super restaurants just 5 min away! Off the beaten track, very clean & well kept. Behaved, furry friends invited! We have a back-up generator so no power outages!
14 – 21 May
4.99 out of 5 average rating, 365 reviews

Popular amenities for Greencastle holiday rentals

Other great holiday rentals in Greencastle

Guest favourite
Farm stay in Chambersburg
The Little White House
4 – 11 Jan
4.94 out of 5 average rating, 67 reviews
Guest favourite
Guesthouse in Mercersburg
The Haven
24 – 31 Aug
4.89 out of 5 average rating, 28 reviews
Guest favourite
Tiny home in Greencastle
Tiny House 3.0
4 – 11 May
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Greencastle
Beautifully Restored Stone Farmhouse
1 – 8 June
5.0 out of 5 average rating, 23 reviews
Guest favourite
Dome in Mercersburg
StayAround Dome ~ Unique & Tranquil Gem ~ Hot Tub
30 Aug – 6 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Hagerstown
Hawks Nest Hagerstown
22 – 29 June
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Hagerstown
Cozy & relaxing private apartment
21 – 28 Aug
4.94 out of 5 average rating, 33 reviews
Guest favourite
Home in Hagerstown
Modern, one bedroom home in Hagerstown
12 – 19 Oct
4.91 out of 5 average rating, 97 reviews
Guest favourite
Tiny home in Mercersburg
Boxed Inn ~ Hot Tub ~ Fire Pit.
19 – 26 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Apartment in Hagerstown
Private, relaxing, quiet, 2 bdrm unit, Sleeps 4-6
3 – 10 Aug
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Mercersburg
Guesthouse tucked back in-between farmland views.
13 – 20 June
4.8 out of 5 average rating, 71 reviews
Guest favourite
Home in Mont Alto
Rancher in Mont Alto
13 – 20 Feb
4.86 out of 5 average rating, 51 reviews

Destinations to explore