Holiday houses in Waynesboro

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Top-rated holiday rentals in Waynesboro

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Guest favourite
A charming cabin is nestled among lush greenery, featuring a large covered porch that extends along the front. The surrounding area includes well-maintained grass and several trees, creating a serene outdoor environment that invites relaxation.
Cabin in Myersville
4.95 out of 5 average rating, 321 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the creek on 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. Great place to unwind & de-stress. 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

Guest favourite
A stylish living area features a cozy sofa facing a modern coffee table. Black walls provide a dramatic backdrop to the space, complemented by golden curtains framing large windows. A sleek bookshelf and a decorative fireplace enhance the room's character, while a circular rug adds warmth.
Apartment in Chambersburg
4.92 out of 5 average rating, 142 reviews

The Study on Main Located on the Square!

Enjoy this stylish apartment at this centrally-located Study on Main St! With hints of painted exposed bricked, original hardwood floors, a full kitchen with new quartz countertops, heating and AC, we know you will love this stylish yet comfortable space we have put together for you! You will be in the heart of downtown Chambersburg, steps away from coffee shops, local favorites for food and shopping, art galleries, the courthouse and our public library! *We ask that all guests sign a renters a

Top Guest favourite
The living area features a spacious sofa in muted tones, complemented by two armchairs and a round dining table with chairs. Soft natural light fills the space, highlighting a blue accent pillow and a decorative wall piece with rural imagery.
Home in Greencastle
4.97 out of 5 average rating, 361 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
Guest suite in Orrtanna
4.97 out of 5 average rating, 180 reviews

Cold Spring Hill

Cold Spring Hill is a studio apartment located in the back of our detached garage. This is a rural setting just minutes away from Michaux State Forest. We are approximately 10 miles from the center of Gettysburg and 8 miles from Liberty Mountain Resort. Whether you are visiting the battlefield, Ski Liberty or hiking the trails, this space offers a relaxing feel after a busy day. Sit back and enjoy the views of wildlife out the windows that over look an apple orchard. We do not allow pets.

Top 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, 119 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
The charming A-frame structure is surrounded by lush greenery, blending seamlessly with the wooded environment. Large windows provide a view into the inviting interior, while a stone pathway leads to the entrance, accentuated by decorative elements and natural landscaping.
Place to stay in Shippensburg
5 out of 5 average rating, 414 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 guesthouse is showcased, featuring a deck with outdoor seating and an umbrella. Tall windows allow for natural light, complementing the green siding. Lush landscaping surrounds the house, creating a natural, inviting setting.
Guesthouse in Smithsburg
4.97 out of 5 average rating, 784 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's Guesthouse is the perfect get-away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Superhost
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
4.81 out of 5 average rating, 233 reviews

Adventure with the Family - Pets Welcome

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.

Top Guest favourite
A spacious bed is positioned against a dark wall, featuring exposed brick accents. Natural light enters through a large window, illuminating soft textiles and decorative pillows. A cozy seating area includes a textured throw blanket and pillows, paired with plants that add a touch of nature.
Apartment in Chambersburg
4.99 out of 5 average rating, 194 reviews

REmix REtreat, curated and styled by REmix Design

Enjoy downtown Chambersburg in this biophilic, sustainable loft, central to local shops, restaurants, breweries, and coffee shops. The building that houses the loft was erected in the 1890s, giving the space charm unique to the era. Wander down Main St get a feel for our quaint downtown. There is a rail to trail within one block of the space for exercising and biking. Chambersburg is a thirty minute drive to Gettysburg, and less than two hours from Baltimore and Washington DC.

Top Guest favourite
The entrance features a welcoming porch area surrounded by colorful potted plants and flowers. A wooden rocking chair sits on the deck, complemented by a textured area rug. Double doors with grid-patterned glass provide access to the suite, framed by lush greenery.
Guest suite in Hagerstown
5 out of 5 average rating, 488 reviews

Oak Hill Private Suite Historic North End

A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Top 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
4.95 out of 5 average rating, 128 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 tree-lined driveway leads to a charming home, partially obscured by lush greenery. Sunlight filters through the leaves, casting gentle shadows on the well-maintained lawn. The sky is bright with fluffy clouds, contributing to a serene, inviting atmosphere.
Home in Hagerstown
4.72 out of 5 average rating, 117 reviews

Private Country Club Home

I am an experienced super host with eight years of hosting. I have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful two acre backyard, a fire pit, outdoor deck and grill, private living room, kitchen, bath, and bedroom. We are just 20 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian trail, and C&O Canal. Come join us for a relaxing stay.

Popular amenities for Waynesboro holiday rentals

Quick stats about holiday rentals in Waynesboro

  • Total holiday rentals

    Explore 10 holiday rentals in Waynesboro

  • Nightly prices starting at

    Waynesboro holiday rentals start at $76 AUD per night before taxes and fees

  • Verified guest reviews

    Over 340 verified reviews to help you choose

  • Wi-Fi availability

    10 of Waynesboro holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Waynesboro rentals

  • 5 Average rating

    Waynesboro stays are highly rated by guests—averaging 5 out of 5!