Vacation rentals in Shady Grove

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Top-rated vacation rentals in Shady Grove

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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

G$23,634 GYD 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

G$24,310 GYD 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

G$28,880 GYD 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

G$21,003 GYD 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

G$17,048 GYD per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 643 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota 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.

Apr 12 – 19

G$19,582 GYD per night

Guest favorite

Place to stay in Hagerstown

4.95 out of 5 average rating, 364 reviews

Springhouse 1803 - easy I-70/81 access

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. If you're looking for a day that is blocked, you can inquiry if its available, see below for more details.

Oct 5 – 12

G$27,867 GYD per night

Superhost

Apartment in Greencastle

4.81 out of 5 average rating, 47 reviews

Rose Rest

Enjoy this small peaceful and centrally-located apartment right off the Square in Greencastle. the bedroom is small but it has a cozy comfy queen bed in it. Close to locally owned coffee shops and restaurants, as well as other mom and pop shops! This apartment is right close to Interstate 81. And about 15 min from Chambersburg, Waynesboro, and Hagerstown Hospitals. About 25 min from White Tail Ski and Golf. 15 min from Mercersburg Academy.

Jun 15 – 22

G$17,120 GYD 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

G$28,167 GYD 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.

Dec 8 – 15

G$18,179 GYD per night

Guest favorite

Guest suite in Chambersburg

4.89 out of 5 average rating, 135 reviews

Cute Place Just Out Of Town With A Country Feel

Looking for an affordable place to stay the night or a few days? You may have just found the perfect place. This cute efficiency unit may just cover all the bases you need for a short stay. What once was a office for a shop, is no longer needed as an office and so it was converted to supply a place to sleep for tired travelers or for people looking to get away for a few days.

Aug 30 – Sep 6

G$13,817 GYD 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

G$21,489 GYD per night