Vacation rentals in Greencastle

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Quick stats about vacation rentals in Greencastle

Nightly prices starting at
Greencastle vacation rentals start at €26 per night before taxes and fees
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Over 380 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Greencastle rentals
4.8 Average rating
Greencastle stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Greencastle

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

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Top guest favorite

Home in Greencastle

Country 2-Bed/2-Bath Barndominium-Dogs Welcome

Pets Welcome - Dogs Only. 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. 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

4.97 out of 5 average rating, 435 reviews

Top guest favorite

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.

4.94 out of 5 average rating, 570 reviews

Superhost

The exterior of a duplex features a beige brick facade complemented by light grey siding. The entrance is marked by a white door, adorned with a circular wreath, and flanked by two large windows showcasing evenly placed shutters. A small table is positioned near the door, enhancing the welcoming ambiance.

Home in Greencastle

The Quick Escape

Welcome to your Quick Escape! *prof. photos & more updates soon* This cozy duplex offers a fenced in yard, lovely rooms & open living space for you to enjoy food, games and gathering together! The spacious bedrooms offer airy, bright feels so you can relax and feel at home during your stay Indulge in the outdoor space by catching the sunrise on the patio or stay warm by the fire! The home is in a prime location for food, shopping, skiing, golfing, and if you just need a quick place to stay!

4.77 out of 5 average rating, 113 reviews

Top guest favorite

A covered patio area is presented with a picnic table and a decorative rug. Lush flower beds filled with vibrant blooms line the space, adding color and charm. A small wooden chair enhances the inviting outdoor setting.

Apartment in Hagerstown

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

My mother said over and over again, “The most beautiful place in Washington County “. Start your day with a brisk walk on a nearly 1 mile path that surrounds the perimeter of this beautiful farmland property. Enjoy your morning coffee as you listen to the birds. Relax in a rocking chair on the gazebo as you watch the sun go down behind the mountains. Less than 10 min from I 70 and I 81 and 20 min from Whitetail Ski. Don't expect everything brand new, but expect everything to be neat and clean.

4.99 out of 5 average rating, 181 reviews

Guest favorite

Home in Hagerstown

The Palmstead | Stylish 3 BR | Garage EV Charging

Welcome to your Hagerstown home base — a brand-new, thoughtfully designed space that’s comfortable, calm, and easy to settle into. Near I-81 & I-70, it features 3 queen beds and 2.5 baths, including a primary bath with heated floors. Enjoy a fully equipped kitchen, coffee bar, washer/dryer, EV garage parking, dedicated workspace, and curated amenities. Minutes to downtown Hagerstown, Meritus Medical, and the Field House. Quiet, private, and perfect for groups, families, or weekend getaways.

5.0 out of 5 average rating, 10 reviews

Top guest favorite

A cozy living area is featured, showcasing a wooden entertainment unit with a television. A green armchair and a dark gray sofa are positioned for comfort. Natural light filters through the window, highlighting the light wood flooring and decorative accents.

Condo in Chambersburg

One-bedroom apartment with separate entrance.

Adorable one-bedroom apartment with separate entrance. Located 10 minutes from downtown Chambersburg. Whether its historical sight-seeing, culturally diverse restaurants, or local craft beer, there is plenty to see and do in this area. Built in 2021, this apartment is on the lower level of our custom built home. It also has a treadmill in the gym. We live upstairs with our two children and two dogs. We maintain quiet hours between 10pm and 7am. Pet friendly, No smoking, No parties.

4.97 out of 5 average rating, 611 reviews

Top guest favorite

A white farmhouse is set against a backdrop of open green fields under a partly cloudy sky. A porch with a few chairs is visible at the front, and a small grill is placed on the lawn nearby. A clear pathway leads to the house.

Farm stay in Chambersburg

The Little White House

Relax on the farm with a peaceful view and rural atmosphere, with the convenience of being close to local attractions. Located close to I-81, it’s a favorable location but private setting. Within 20 minutes of Chambersburg restaurants, shopping, hospital and activities. Also about a 40 minute drive to historic Gettysburg, PA! The farm is active farm growing row crops and hay. We have a very friendly barn cat! We are a family wanting to share our beautiful piece of land with all who visit!

4.95 out of 5 average rating, 150 reviews

Top guest favorite

The exterior of the historic colonial house is depicted, showcasing a light stone facade complemented by a slanted metal roof. A spacious front porch with a wooden railing is visible, surrounded by a well-maintained garden featuring various plants. Two doors lead into the home.

Cottage in Hagerstown

Unique historic home - Springhouse 1803

If you are looking for a unique place to stay, come visit us at Springhouse 1803. Yes, there really is a spring under the house. After sitting empty for 20+ years, the house has been restored to be lived in again and it has maintained much of its colonial charm. The house has all the amenities you need for a comfortable stay. NOT A PARTY HOUSE, OWNER IS ON SITE in separate house. If you're looking for a day that is blocked, you can inquiry if it's available, see below for more details.

4.96 out of 5 average rating, 468 reviews

Top guest favorite

The A-frame cottage features a striking wooden exterior with a stone chimney. Large windows provide views of the surrounding greenery, while manicured shrubs and ornamental grass add to the landscaping. The structure's design is complemented by a clear blue sky overhead.

Cabin in Chambersburg

Cedarhill Cottage with Cozy Fireplace

Nestled in Franklin County, this quaint A-frame cottage is a perfect destination. If you are looking for a place to get away and defrag from your busy life, this newly remodeled A-frame cottage offers all the comforts of home in a quiet area that has been described as refreshing and renewing. Surrounded by views and the sounds of nature and within minutes of local shopping and dining - you’ll quickly see why our guests become family. Sit by the fire pit and make some s'mores!

4.95 out of 5 average rating, 258 reviews

Top guest favorite

Townhouse in Greencastle

The State Line Stay

Our townhome offers the perfect blend of comfort, convenience, and location. Situated on the Maryland/Pennsylvania state line in Greencastle, this home is just minutes from Interstate 81, making it an ideal choice for work travelers, contractors, and guests seeking easy access to surrounding areas. Unlike a hotel, you’ll enjoy the privacy of an entire two-bedroom, 2.5-bath home with a one-car garage and in-unit washer and dryer—perfect for both short and extended stays.

5.0 out of 5 average rating, 28 reviews

Top guest favorite

The exterior of the house is shown, enhanced by a blanket of snow. A welcoming porch features two rocking chairs, while snow-covered shrubs line the path to the door. A soft glow from the sunset is visible in the sky beyond the property.

Farm stay in Greencastle

Country Home with a Wonderful View

Welcome to our house in the country. Located on a quiet country road you can sit on the porch and watch the sunset over the Mountains to the west. When the weather is warm, we host goat yoga at our farm with our Nigerian Dwarf Goats. We are located less than nine scenic miles away from Whitetail Resort and Mercersburg Pennsylvania. Cushwa Basin on the C&O Canal is less than 14 miles away. We are also a short drive away from Antietam and Gettysburg National Battlefield.

4.94 out of 5 average rating, 149 reviews

Top guest favorite

A spacious living area features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a neutral area rug, while natural light flows through two diamond-pane windows. In the background, the open kitchen and dining space are visible.

Home in Saint Thomas

Private 4BR Hideaway | Pavilion & Firepit

The Parnell Hideaway nestled in the woods of south central Pennsylvania offers a spacious home for up to 8 guests. This retreat features two king and two queen bedrooms, two full-size bathrooms and an open kitchen-dining-living room area. With designated spaces for games, reading and work, plus a laundry room, the Parnell Hideaway offers ample room for relaxation and productivity. Outdoor amenities include a pavilion, picnic table, propane grill, firepit and corn hole.

4.98 out of 5 average rating, 64 reviews