Holiday rentals in Clear Spring

4.94 out of 5 average rating, 112 reviews

Chalet in Mercersburg

Amazing Whitetail Ski Holiday and Mountain Retreat

Welcome to our beloved Mountain home. Located at Whitetail resort you can walk to the slopes and enjoy the après ski in our beautiful cozy house with cabin feel. Perfect ski holiday, weekend getaway, or place to work remotely with high-speed internet. Only 1.5 hours from DC & Baltimore. This is the perfect place to escape the city, connect with nature and recharge. A place to build up fond memories. All season adventures, enjoy skiing, swimming, hiking, golfing, fishing, lakes and local farms.

4.97 out of 5 average rating, 306 reviews

Home in Greencastle

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

4.92 out of 5 average rating, 263 reviews

Bear Pines Retreat ~ Game Room ~ Screened Porch

Come enjoy this 3 bedroom/2 bath A frame cabin in The Woods. Bear Pines Retreat features 2 bedrooms on the lower level with 4 beds and full bathroom. The Master Suite loft has a queen bed with mountain spa bathroom. You can connect to the built in Bluetooth speaker and play some relaxing music while looking out the skylight above. The living area has plenty of seating with wood burning fireplace and 55” TV mounted above. You can enjoy over 100 cable channels, music and streaming services.

4.98 out of 5 average rating, 125 reviews

Flat in Hagerstown

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

My mother said over and over again, “The most beautiful place in Washington County “. Start your day with a brisk walk on a nearly 1 mile path that surrounds the perimeter of this beautiful farmland property. Enjoy your morning coffee as you listen to the birds. Relax in a rocking chair on the gazebo as you watch the sun go down behind the mountains. Less than 10 min from I 70 and I 81 and 20 min from Whitetail Ski. Don't expect everything brand new, but expect everything to be neat and clean.

Guest suite in Smithsburg

4.98 out of 5 average rating, 259 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.

4.84 out of 5 average rating, 198 reviews

Townhouse in Hagerstown

Darling Duplex

*NO cleaning fees in 2025!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly •Entire private home •Central HVAC (dual units) •Walk-in shower •Fenced-in backyard •Full size washer and dryer (with essentials!) •Dishwasher/Garbage disposal •Piano •Multiple bathrooms and beds • and so much more! Comfy 100 year old duplex minutes away from downtown. Remodeled kitchen and posh upstairs bath. A short walk to the beautiful Hagerstown city park.

Guest suite in Hagerstown

5 out of 5 average rating, 465 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

Cabin in Falling Waters

4.93 out of 5 average rating, 103 reviews

Peregrine's Perch - Cabin Overlooking the River!

MOUNTAIN MAMA VACATION HOMES The view from this cabin will take your breath away. Perched atop a cliff overlooking a peaceful stretch of Potomac River, you couldn't ask for a better place to leave the world behind. With an outdoor fire pit and an indoor wood stove, this beautiful cabin has everything you need to stay cozy year-round. And the chic decor and luxurious renovation is just what you're looking for. If you're searching for a cabin getaway then look no further!

Superhost

4.88 out of 5 average rating, 169 reviews

Unique Gem: Cozy A frame cabin in the woods

Come unwind and enjoy nature in this cozy, quaint, A-frame cabin. Nestled in the woods overlooking a community pond, enjoy the views through floor to ceiling windows or relax outside on one of the two large decks. The home includes a gas grill available for use and fire pit with wood provided. Best suited for two guests, it can accommodate up to 4 with use of the futon in the loft. Located just minutes away from the Potomac River and numerous recreational areas!

4.98 out of 5 average rating, 134 reviews

Tiny home in Mercersburg

Boxed Inn ~ Hot Tub ~ Fire Pit

This charming, tiny home offers the perfect blend of cozy comfort and the great outdoors, all while nestled close to the Whitetail Resort. Inside is an open space bathed in natural light, where modern style meets mountain tranquility. The interior, with its thoughtfully designed features, comes with a comfortable loveseat, a smart TV, and bar seating: perfect for those intimate conversations or just catching up after a busy day on the trails.

4.9 out of 5 average rating, 106 reviews

Home in Clear Spring

Cozy Creek House W/Hot Tub by Whitetail

Here is our Cute little cottage home facing Conococheague Creek, Come sit on the back deck enjoying the hot tub or sitting on one of the chairs enjoying the fire pit. Our home is located in central location, short ride to the famous Whitetail Resort, minutes to Hagerstown Speedway, so many local attractions, dining and shopping near. House has wifi and has 3 TVs through out the home. Can take a break and work from our little home if needed.

4.93 out of 5 average rating, 286 reviews

Cottage in Shepherdstown

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!

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Other great holiday rentals in Clear Spring

Home in Hagerstown

4.68 out of 5 average rating, 80 reviews

Private Country Club Home

ChristinaRating, 5 stars1 week ago

Maryanne communicated very well with us. She gave us specific directions, and made it very easy for us to get in. Her place was as described, and was perfect for a night getaway! Thank you for having us!

4.94 out of 5 average rating, 72 reviews

Modern w/Hot Tub, Sauna, WiFi, Fire Pit, Grill/Dec

BrendonRating, 5 stars1 week ago

We loved our stay at Tony’s cabin! Everything was fantastic and cozy. We truly felt right at home and relaxed. Tony communicated well and was proactive, which made the whole process easy and seamless. The sauna was AMAZING! We definitely will come back.

4.88 out of 5 average rating, 8 reviews

The Pinecone

StevieRating, 5 stars1 week ago

The Pinecone is a very nice and peaceful cabin in the woods for a family getaway. There's a stream running by as beautiful ambience when you're outside, but also noise insulation indoors. The loft was fun and secure for the kids. A private bedroom is also nice. The decorations and instructions helped us feel right at home and out on adventure. We do recommend. Thank you, Jodie!

Home in Berkeley Springs

4.94 out of 5 average rating, 94 reviews

Simply Scandi- Modern Mt Retreat

LaurenRating, 5 stars3 weeks ago

This was the perfect house for our family of 5 to stay at while visiting for a mountain bike race! It was clean, lots of space and amenities, and the beds were comfortable! Would definitely stay here again.

5 out of 5 average rating, 32 reviews

Home in Martinsburg

So cozy

NicoleRating, 5 stars1 week ago

After a 12-hour drive, this home was the perfect place to walk into—so cozy, clean, and welcoming. The space had a warm, homey feel, cute decorations, and everything was super organized. Jamie thought of everything—bathroom essentials, coffee, snacks—it was really nice to have that available right away after a long day/night of traveling. We were so impressed with the attention to detail and how comfortable the whole place felt! The outside of the home is just as beautiful. It’s set in the back of a quiet neighborhood with large lawns, a roomy driveway for parking. There is also a back patio that was super cute and a peaceful spot to relax. Jamie is an amazing host: friendly, quick to respond, and happy to help with anything we needed. She was incredibly sweet, easy to talk to, and made us feel like we were staying with our favorite aunt. Her warmth and thoughtfulness made the whole experience even better. We’d absolutely stay here again!

Home in Falling Waters

5 out of 5 average rating, 8 reviews

Belvedere On The Potomac

SeanRating, 5 stars1 month ago

This is the second time staying here and we absolutely loved it. It’s so private and beautifully maintained. Would highly recommend to anyone looking for a beautiful and private getaway with friends and family.

4.78 out of 5 average rating, 9 reviews

Home in Hedgesville

Potomac Princess

CathrynRating, 5 stars2 weeks ago

This is a wonderful little getaway! We stayed for the weekend and the river was lovely, and there are lots of hiking, fishing, swimming, and boating spots in the area. The house was adorable and exactly as described, and Rachel’s instructions were very detailed and clear and extremely helpful. Would absolutely stay again!