Vacation rentals in Clear Spring

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Top-rated vacation rentals in Clear Spring

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Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 567 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Aug 1 – 8

G$17,575 GYD per night

Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 252 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.

Sep 6 – 13

G$23,628 GYD per night

Guest favorite

Apartment in Clear Spring

4.99 out of 5 average rating, 365 reviews

Clean, quiet. Whitetail, I-70/I-81 15 min away!

Come, relax and enjoy your stay in the area with us! The perfect HideAway to hang your hat, let your hair down or to enjoy privacy, peace & quiet while you work online on your laptop. Ski day/evening during the winter or golf during suitable weather at Whitetail. Visit other attractions including National Parks to visit, hike or bike. Super restaurants just 5 min away! Off the beaten track, very clean & well kept. Behaved, furry friends invited! We have a back-up generator so no power outages!

Nov 5 – 12

G$24,083 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

Aug 9 – 16

G$24,303 GYD per night

Guest favorite

Guest suite in Mercersburg

4.94 out of 5 average rating, 406 reviews

The 1780 Cabin on Main

A charming cabin built circa 1780 situated right on Main Street, just steps from Pubs and Restaurants and easy walking distance to historic Mercersburg Academy. There is a separate sleeping area upstairs with a queen-size memory foam bed. The lower level features a foldout couch and air mattress for additional guests, as well as a 55" TV and a wet bar and bathroom. Visitors have universally enjoyed the cabin's cozy feel. While there is no yard available, the town is great for walking dogs.

Oct 22 – 29

G$24,338 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 5 – 12

G$20,616 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.

Nov 13 – 20

G$19,490 GYD per night

Guest favorite

Tiny home in Hancock

4.95 out of 5 average rating, 151 reviews

Ridge top tiny house - mountain side views

Reconnect with nature in this unforgettable tiny house. Perched on the top of a ridge offers great views of the mountains. Modern contrasting interior with the charm only a tiny house can bring. The mountains from three different states (PA, MD, WV) can be seen from within the tiny house. Sitting on the edge of 275 acres of farmland means you will be sure to hear the turkeys gobble during the daytime or the whippoorwill at night. Relax and enjoy the scenery from the loft bed.

Sep 1 – 8

G$38,582 GYD per night

Guest favorite

Cabin in Berkeley Springs

4.82 out of 5 average rating, 290 reviews

Cozy Cabin Creek Retreat W/Hottub

The neighborhood is super quiet and such a wonderful place to get away to. The house is located right in front of the creek that you can fish, kayak, let your dog swim and just enjoy the sound. The house is nice and cozy, the house is not secluded. I do have neighbors, the ones to the left is a rental, the one to the right is a weekend home but the couple are never there. The walk down to the water is little steep, I do not have stairs yet to the bottom of the hill yet.

Dec 3 – 10

G$27,494 GYD per night

Guest favorite

Bungalow in Great Cacapon

4.9 out of 5 average rating, 465 reviews

Rooster Wrest in the Trees

Sweet 2 bedroom bungalow. Ideal for lovers, or a quiet beautiful retreat environment. Rooster has 1 full bath. Living room with satellite TV, Netflix; wood burning stove fireplace, wood provided, fully equipped kitchen, dining table, linens and starter paper goods furnished. Large deck and screen porch looking out on Cacapon Mountain. Hot tub off master bedroom deck in trees, feels like a tree house. Many mornings mist rises up from river, half mile away as crow flies.

Dec 7 – 14

G$20,614 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 14 – 21

G$28,465 GYD per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 181 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

Nov 13 – 20

G$25,230 GYD per night