Vacation rentals in Waynesboro

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Top-rated vacation rentals in Waynesboro

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Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 253 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across 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. Amazing place to unwind, de-stress & get away. 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.

Dec 13 – 20

$98 per night

Guest favorite

Home in Greencastle

4.97 out of 5 average rating, 194 reviews

Country 2-Bed/2-Bath Apartment with 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

Mar 27 – Apr 3

$102 per night

Superhost

Home in Waynesboro

4.81 out of 5 average rating, 174 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.

Sep 16 – 23

$119 per night

Guest favorite

Home in Fairfield

4.97 out of 5 average rating, 117 reviews

The Stone House on the Green

Come and enjoy a relaxed getaway at our circa 1850 Stone House that is nestled in beautiful Carroll Valley, at the base of Ski Liberty Mountain Resort, and on the 3rd hole of Carroll Valley Golf Course. In addition, our home is across the street from a park with playgrounds, a fishing pond, Tom's Creek, the library, and a walking path. Only minutes to the historic downtown Gettysburg and battlefields, and close to local restaurants, this spot is the perfect place to see, do, rest and relax.

May 24 – 31

$128 per night

Guest favorite

Guest suite in Smithsburg

4.99 out of 5 average rating, 152 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, dog-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 4 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Mar 16 – 23

$75 per night

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 190 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Jul 4 – 11

$88 per night

Guest favorite

Home in Myersville

4.97 out of 5 average rating, 147 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!

Sep 26 – Oct 3

$145 per night

Guest favorite

Guest suite in Fairfield

4.89 out of 5 average rating, 131 reviews

Gettysburg-Ski-Golf-ATHikes - RoseSniffers Loft

Calling all RoseSniffers!! Stop and smell the roses in this newly constructed, stylish studio with private entrance. Although you will wake up to a bird's eye view of mountains, farms, and a golfcourse, you will be minutes away from four-season adventures: Skiing, Antiquing, Vineyards, History, Gettysburg Military Park, 5-Star Golfing, Performing Arts, and Dining are all minutes away! We've thought of all your comforts of home and designed this place with your peace in mind!

Aug 17 – 24

$73 per night

Guest favorite

Guest suite in Hagerstown

4.99 out of 5 average rating, 397 reviews

Oak Hill Private Suite Historic North End

A recently renovated private suite in historic home 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, Antietam, Gettysburg, Frederick, C&O bike trail, wineries and outlets. Guests have enjoyed stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Oct 7 – 14

$71 per night

Guest favorite

Home in Blue Ridge Summit

5.0 out of 5 average rating, 450 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.

Sep 12 – 19

$118 per night

Guest favorite

Condo in Chambersburg

4.98 out of 5 average rating, 223 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.

Nov 6 – 13

$76 per night

Guest favorite

Guest suite in Hagerstown

4.99 out of 5 average rating, 399 reviews

Spacious and Comfortable Private Living Space

Hagerstown is known as "The Hub" for good reason! Our place is conveniently located close to Interstates 81 and 70. You’ll love our place because of the comfortable living space. We want you to feel at home. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

Jun 19 – 26

$90 per night