Holiday rentals in Waynesboro

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Top-rated holiday rentals in Waynesboro

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Guest favourite

Flat in Chambersburg

4.92 out of 5 average rating, 132 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

Home in Greencastle

4.97 out of 5 average rating, 306 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 favourite

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.

Guest favourite

Cottage in Waynesboro

4.94 out of 5 average rating, 103 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

Guest suite in Smithsburg

4.98 out of 5 average rating, 260 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

Home in Smithsburg

4.95 out of 5 average rating, 143 reviews

The Great Escape Lodge ~ Exquisite Mountain Views

The Great Escape Lodge is a soaring A-frame offering luxury accommodations. Owner designed and custom built in 2022, this luxury getaway is nestled in the stunning Catoctin Mountains with views parallel to those seen on Paramount's hit series Yellowstone. This exquisite residence offers outstanding interior and exterior custom touches and amenities. From the open concept great room to the massive deck with rockers and hot tub, there are endless opportunities to enjoy the scenic views.

Guest favourite

Flat in Greencastle

4.83 out of 5 average rating, 35 reviews

BackPorch Cottage of Greencastle

Come and Enjoy Back Porch Cottage of Greencastle. Spacious unit with Full Kitchen and Dining Area. Cozy sleeping nook with full size bed topped with luxurious bedding. Relax in the sitting area to watch Tv or Read a Book. And of course you can't come to BackPorch cottage without enjoying the back porch. Complete with Rocking Glider chairs and your own personal walk way to the Parking lot. Minutes from Downtown shops and restaurants, Pubs,all within walking distance from this unit.

Guest favourite

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 favourite

Flat in Chambersburg

4.99 out of 5 average rating, 167 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

Guest suite in Hagerstown

5 out of 5 average rating, 466 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

Holiday 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 favourite

Home in Blue Ridge Summit

4.99 out of 5 average rating, 559 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.

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Popular amenities for Waynesboro holiday rentals

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Other great holiday rentals in Waynesboro

Guest favourite

Private room in Hagerstown

4.95 out of 5 average rating, 44 reviews

Serenity and Comfort

JessicaRating, 5 stars2 weeks ago

I was in town for a wedding and she let me drop off my luggage early. Very considerate. Clean, simple, and safe place to stay. I enjoyed the chocolate she left for me! I will definitely consider renting with her again.

Guest favourite

Home in Mont Alto

4.89 out of 5 average rating, 73 reviews

Rancher in Mont Alto

MichaelRating, 5 stars3 weeks ago

Loved everything about it. Was a great house, nice furnishings, nice neighborhood, and great price. We needed a place to stay so we could attend our sons wedding, and it was the perfect choice.

Guest favourite

Private room in Orrtanna

4.96 out of 5 average rating, 23 reviews

BDR 1: 3 si.OR 1si.& 1 king, main floor, pr bath

WillRating, 5 stars1 week ago

I stayed at Eleanor Rose's to photograph the aurora borealis. The aurora turned out to be a bust, but the stay was perfect. As a photographer, I needed a location with an expansive view to the north - and this location fit the bill! The house reminded me of my grandmother's house -- right down to the old farmhouse door knobs. But it had all the amenities I needed -- and lots of hot running water to wash up!! Plus, Eleanor Rose bakes a yummy raisin molasses pastry for breakfast. I would definitely return!!

Guest favourite

Home in Fairfield

5 out of 5 average rating, 9 reviews

Cozy Mountain Retreat - Remodeled Near Ski Resort

MichaelRating, 5 stars2 weeks ago

Wonderful home in a great area! Rented the house for our wedding party and we only have good things to say about our stay!

Top guest favourite

Private room in Sharpsburg

4.96 out of 5 average rating, 114 reviews

Hidden Gem - Stay with Dan and Alice.

SueRating, 5 stars2 weeks ago

This was my second time staying at Hidden Gem and it was as lovely as the first. Daniel is an excellent host - great communication and thoughtful responses. The room is spacious and has a wonderfully comfortable bed and the entire place is spotlessly clean. The patio and fish pond are so very peaceful. And the pups are adorable! Highly recommend.

Top guest favourite

Private room in Chambersburg

4.95 out of 5 average rating, 103 reviews

Robin’s Creekside Retreat

MikeRating, 5 stars2 weeks ago

Sweet ideal getaway if you want to just get away and relax. Comfy and cozy, we felt like we didn't want to leave. Robin was very helpful with any questions we had. It's in the middle of the countryside but has plenty of shopping and restaurants not too far away. My wife and I loved it. Mike

Guest favourite

Cottage in Thurmont

5 out of 5 average rating, 13 reviews

The Kelbaugh Cottage

LisaRating, 5 stars1 week ago

the place was as described clean, neat & the beds were comfortable. The only thing that was missing ( unless I didn't see it) was an iron. I would recommend this place.

Guest favourite