Vacation rentals in Waynesboro

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Top-rated vacation rentals in Waynesboro

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Top guest favorite

A rustic cabin with a wooden exterior nestled among trees is illuminated by warm outdoor lighting. A welcoming entrance features a green door, surrounded by flower pots and small pumpkins. A rocking chair sits on the front porch, inviting relaxation in the tranquil setting.

Cabin in Myersville

4.98 out of 5 average rating, 142 reviews

Sleepy Hollow Log Cabin

Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

Guest favorite

A stylish living area showcases a dark accent wall adorned with elegant wall shelves filled with decorative items and books. A contemporary round coffee table is centered on a textured area rug, while a muted chair sits nearby. Natural light flows in through large windows, complemented by warm drapes.

Apartment in Chambersburg

4.92 out of 5 average rating, 133 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 favorite

Two outdoor chairs are positioned on a concrete patio, facing a door that provides access to the interior. The chairs feature a neutral fabric and metallic frames, set against a backdrop of blue and silver paneling.

Home in Greencastle

4.97 out of 5 average rating, 311 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

Guest favorite

Home in Waynesboro

4.83 out of 5 average rating, 219 reviews

Adventure with the Family - Pets Welcome

The cozy house for the whole family, furry friends 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 favorite

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, 748 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.

Top guest favorite

The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.

Home in Myersville

4.97 out of 5 average rating, 227 reviews

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

Guest favorite

Cabin in Chambersburg

4.95 out of 5 average rating, 234 reviews

Cedarhill Cottage

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!

Guest favorite

A view from the window showcases the exterior of the Coyle Library. The building features large columns and glass doors, framed by a decorative facade. Snow is visible on the steps, with a clear blue sky in the background and greenery from the window’s nearby plant.

Apartment in Chambersburg

4.99 out of 5 average rating, 169 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 favorite

A bright bathroom area features a jetted soaking tub surrounded by soft stone tiles. A potted orchid adds a touch of elegance, while natural light filters through frosted glass windows. A candle and neatly rolled towels enhance the serene atmosphere.

Guest suite in Hagerstown

5 out of 5 average rating, 467 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.

Superhost

Vacation home in Waynesboro

4.84 out of 5 average rating, 175 reviews

Beautiful Mansion, Pool, Fishpond & Home Theater

Nestled on 3 beautifully landscaped acres, this 7-bedroom, 5.5-bath mansion offers the utmost privacy and modern comfort, sleeping up to 32 guests. With over 5,000 sq.ft of lying space, enjoy two full kitchens, a home theater with Bose surround sound, fitness center, and a lush backyard with a swimming pool, gazebo, and scenic pond. Additional amenities include an indoor pool table, outdoor dining area, and dedicated workspace.

Top guest favorite

The exterior of a colonial era spring house is depicted, featuring a stone base and wooden upper levels. Lush greenery surrounds the structure, with hanging planters adding color. Two wooden chairs are positioned near the entrance, inviting relaxation in a serene outdoor setting.

Home in Blue Ridge Summit

4.99 out of 5 average rating, 561 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.

Top guest favorite

A charming house features a stone exterior with a gabled roof and decorative window trim. Surrounded by a lush green lawn, outdoor seating can be seen on the front porch. The clear blue sky provides a bright and open backdrop for this inviting space.

Condo in Chambersburg

4.97 out of 5 average rating, 394 reviews

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 fully equipped gym. Pet friendly, No smoking, No parties.