Holiday houses in Waynesboro

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Top-rated holiday rentals in Waynesboro

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Guest favourite
A charming cottage exterior features a gray metal roof and a welcoming entry with blue trim. A covered porch invites relaxation, while two wooden chairs and a small table provide a cozy outdoor seating area. Lush green grass surrounds the property.
Cottage in Orrtanna
4.9 out of 5 average rating, 145 reviews

Sweet Gettysburg Area Cottage Close to Outdoor Fun

Off the beaten path but close to it all, including historic Gettysburg, the Appalachian Trail, Caledonia State Park, and Michaux State Forest. Relax on a large screened-in porch, in the shade of our pines or on the banks of a mountain creek. Access your own streaming accounts through our TV/wifi. Great restaurants are nearby, or make use of our original 1950s efficiency kitchen and dine al fresco. You’re surrounded by wineries, farm markets and even a candy store. Central location to do it all!

Top Guest favourite
Home in Greencastle
4.97 out of 5 average rating, 384 reviews

Country 2-Bed/2-Bath Barndominium w/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

Top Guest favourite
A comfortable living area features a spacious leather couch adorned with soft pillows, along with an armchair and a blue accent chair. Natural light illuminates the space, highlighting a serene landscape painting on the wall and a cozy throw blanket draped on the side chair.
Home in Chambersburg
4.97 out of 5 average rating, 104 reviews

Spacious Home Minutes from Penn Nat. Golf Course

We are located minutes from Penn National Golf Course, Caledonia Golf Course and State Park, the Appalachian Trail, shopping and restaurants. Gettysburg, PA is a 30 min. drive away and DC is less than 2 hours from us. There are several ski resorts close by as well. We live out of town and settle in this home when we are in the area for a few weeks each year. We have attempted to make this space a home for ourselves that you will enjoy as well. Our daughter will be your host for your stay.

Top Guest favourite
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
4.99 out of 5 average rating, 147 reviews

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.

Guest favourite
Two classic wooden Adirondack chairs are positioned near the bank of a gently flowing stream. Lush greenery surrounds the area, with trees casting dappled sunlight on the water. A clear blue sky adds a serene backdrop, enhancing the peaceful atmosphere of the outdoor space.
Cottage in Waynesboro
4.95 out of 5 average rating, 128 reviews

Antietam Toll House~an historic waterfront cabin

The Antietam Toll House (@antietamtollhouse) is a renovated historic property circa 1800. Sitting on the bank-head of the Antietam stream, this cabin has it's own private fishing hole. Secluded, yet close to amenities and attractions, this property is the perfect place for an artist retreat, respite from the city or a base from which to explore local gems of the area. Wineries, Appalachian Trail, Antietam, Gettysburg battlefields, Ski Liberty, Catoctin , Cunningham Falls and more nearby.

Top Guest favourite
Place to stay in Shippensburg
5 out of 5 average rating, 452 reviews

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures! *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Top Guest favourite
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
4.96 out of 5 average rating, 447 reviews

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.

Top Guest favourite
The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.
Guest suite in Smithsburg
4.98 out of 5 average rating, 346 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Guest favourite
A dining area with a wooden table is surrounded by eight matching chairs, featuring a centerpiece of fresh flowers. Soft lighting is provided by a pendant lamp. A staircase with a black railing is visible, leading to a cozy living area with a dark sofa and art on the walls.
Home in Waynesboro
4.82 out of 5 average rating, 243 reviews

Waynesboro Adventure with the Family

The cozy house for the whole family, dogs included. Quietly located in the town of Waynesboro, a short walk to downtown and excellent Sushi - Sapporo. Eat in or explore Waynesboro's charm. 1.5 hours from Baltimore or Washington DC. 23 miles from Historic Gettysburg. 13 miles from Ski Liberty and 23 miles from Whitetail Ski resorts. Covered carport parking. Perfect for the family vacation or ski trip. Stocked with toys and games. Full line of baby amenities available upon request.

Guest favourite
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
4.94 out of 5 average rating, 133 reviews

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 I81, it’s a favorable location but private setting. Within 10-20 minutes of Chambersburg restaurants, shopping, hospital and activities. Also about a 30 minute drive to historic Gettysburg, PA! The farm is active with 2 cows and 3 (way too friendly) cats. We are a small family wanting to share out beautiful piece of land with all who visit!

Guest favourite
A polycarbonate dome is nestled among trees, illuminated in soft green light. The spacious deck includes a seating area and a small table. A colorful sunset is visible in the background, casting a warm glow over the Appalachian landscape.
Dome in Shippensburg
4.91 out of 5 average rating, 148 reviews

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

Top Guest favourite
The exterior of a colonial era spring house showcases a natural stone base supporting a wooden structure. A spacious balcony with wooden railings extends from the second floor. Brightly colored hanging flower pots add a touch of greenery to the inviting façade.
Home in Blue Ridge Summit
4.99 out of 5 average rating, 631 reviews

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

Popular amenities for Waynesboro holiday rentals