Greencastle places to stay

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Greencastle

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 247 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

Mar 19 – 26

$98 per night
Guest favorite

Home in Greencastle

4.97 out of 5 average rating, 184 reviews

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

Jan 15 – 22

$102 per night
Guest favorite

Guest suite in Mercersburg

4.94 out of 5 average rating, 399 reviews

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.

Aug 21 – 28

$105 per night

Popular amenities for Greencastle places to stay

Other great vacation rentals in Greencastle

Guest favorite

Cabin in Chambersburg

4.95 out of 5 average rating, 213 reviews

Cedarhill Cottage

Apr 22 – 29

$191 per night
Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 176 reviews

The GW Hollida Cottage of Shepherdstown

Sep 6 – 13

$106 per night
Guest favorite

Place to stay in Hagerstown

4.95 out of 5 average rating, 362 reviews

Springhouse 1803 - easy I-70/81 access

Jan 10 – 17

$117 per night
Superhost

Townhouse in Mercersburg

4.87 out of 5 average rating, 165 reviews

Resort House

Apr 28 – May 5

$90 per night
Guest favorite

Cabin in Berkeley Springs

4.92 out of 5 average rating, 117 reviews

Foxy's Cabin

Jul 24 – 31

$118 per night
Guest favorite

Cottage in Fairfield

4.96 out of 5 average rating, 244 reviews

The Cottage

Aug 11 – 18

$74 per night
Guest favorite

Guest suite in Sharpsburg

4.92 out of 5 average rating, 170 reviews

Guest Apartment by C & O Canal and Battlefield

Apr 4 – 11

$85 per night
Guest favorite

Cabin in Shepherdstown

4.95 out of 5 average rating, 419 reviews

The Log Cabin

Oct 17 – 24

$93 per night
Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 563 reviews

Historic Scrabble, Shepherdstown

Jun 27 – Jul 4

$81 per night
Superhost

Apartment in Greencastle

4.8 out of 5 average rating, 44 reviews

Rose Rest

May 11 – 18

$71 per night
Superhost

Loft in Greencastle

4.87 out of 5 average rating, 39 reviews

The Loft Of Greencastle

Nov 14 – 21

$75 per night
Guest favorite

Farm stay in Chambersburg

4.94 out of 5 average rating, 69 reviews

The Little White House

Sep 6 – 13

$95 per night

Other great vacation rentals in Greencastle

Guest favorite

Home in Mont Alto

4.86 out of 5 average rating, 51 reviews

Rancher in Mont Alto

Feb 22 – Mar 1

$100 per night
Guest favorite

Home in Hagerstown

4.94 out of 5 average rating, 35 reviews

Cozy & relaxing private apartment

Sep 3 – 10

$78 per night
Guest favorite

Home in Chambersburg

5.0 out of 5 average rating, 34 reviews

Creekside on King

Sep 20 – 27

$116 per night
Superhost

Cottage in Waynesboro

4.91 out of 5 average rating, 68 reviews

Antietam Toll House~an historic waterfront cabin

Nov 17 – 24

$123 per night
Guest favorite

Townhouse in Mercersburg

4.9 out of 5 average rating, 90 reviews

Steps away from Whitetail ski lift with a view!

Aug 12 – 19

$87 per night
Guest favorite

Home in Hagerstown

5.0 out of 5 average rating, 7 reviews

Hawks Nest Hagerstown

Aug 7 – 14

$82 per night
Guest favorite

Apartment in Chambersburg

5.0 out of 5 average rating, 93 reviews

REmix REtreat, curated and styled by REmix Design

Jun 17 – 24

$123 per night
Guest favorite

Apartment in McConnellsburg

4.83 out of 5 average rating, 58 reviews

The Resting Place

Jul 27 – Aug 3

$90 per night
Guest favorite

Tiny home in Greencastle

4.98 out of 5 average rating, 42 reviews

Tiny House 3.0

Jul 18 – 25

$90 per night
Guest favorite

Home in Chambersburg

4.96 out of 5 average rating, 48 reviews

Spacious Home Minutes from Penn Nat. Golf Course

Feb 20 – 27

$82 per night
Guest favorite

Dome in Mercersburg

5.0 out of 5 average rating, 38 reviews

StayAround Dome ~ Unique & Tranquil Gem ~ Hot Tub

Aug 26 – Sep 2

$270 per night
Guest favorite

Guesthouse in Mercersburg

4.89 out of 5 average rating, 28 reviews

The Haven

Aug 30 – Sep 6

$95 per night

Destinations to explore