Holiday rentals in Shepherdstown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Double Decker Screened Porches~Hike to Brewery~

Experience a peaceful escape in Berkeley Springs: 🫧8 person Hot Tub 🌳TWO level screened in porches+Deck 🥾Direct access to hiking trail system (PRO TIP: leads to brewery) 👙Community Pool+Kiddie Pool+Jacuzzi (seasonal) 🛋️2 Family Rooms 🪵Massive Firepit+provided Firewood+Grill 🔥2 Cozy Brick Propane Fireplaces 🎲Poker Table+Bumper Pool+Board Games+DVD Library 🐾Pet Friendly (+fee/approval) 📺WIFI and 65in Smart TV 🛏️5 beds=3KINGS+2Queens 💆🏼‍♀️4 FULL Spa Bathrooms 🛍️5 minutes to downtown

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a getaway in our newly renovated Stone Cottage nestled on hilltop just 15 minutes from Leesburg & less than 90 minutes from DC. The property adjoins next to a hidden state park, not on the map with gentle hiking trails. Secluded location however 10 min to some of the areas finest wineries & breweries. Custom-made king-size bed and fresh interior, are sure to impress . So whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

Magical quiet cabin nestled in the woods

Lovely cabin tucked into the woods where you can relax in nature with complete privacy/seclusion while still close to downtown. 2 bedrooms - the second bedroom is part of a partially open loft. Fully equipped, AC, elec heat, deck, gas grill & view, wifi, DVD player and desk/work area. Loads of amenities and fun things for kids to explore around the property. 10 minutes to downtown Berkeley Springs, near Cacapon Park - for golf, beach/lake access, many fun day trips. 50 minutes to wineries.

Tequila Sunset, Harpers Ferry. Entire first floor!

Welcome to Tequila Sunset in Harpers Ferry, WV! This beautiful, secluded home has stunning sunset views, you'll truly feel on top of the world! 100 mile vista of the gorgeous Blue Ridge Mountains. Entire first floor is yours, no shared spaces! Over 1200 SF of room to unplug & relax. King size Nectar bed, cozy indoor wood burning fireplace, outdoor firepit, 84" TV, & a private deck to enjoy the natural surroundings. Just 2 miles from the renowned Mountain Lake Club and the Appalachian Trail!

*New* River Front Retreat *HotTub-FirePit-Kayak*

Hummingbird Hideaway a River Front Cottage is the perfect place to relax & recharge. *Steps from the cleanest river in WV *Hot tub with river views *Kayaks on property, launch right off property *Decks with BBQ and dining Alfresco *Two Fire pits: River Front Wood Fire pit and Propane on the Deck *Yard games and board games *Wi-Fi and Smart TV. *Pet-Friendly This is a place where time slows down and the soul finds rest. Come step into nature and nurture your spirit at our riverfront haven.

Applemoon: Charming Log Cabin in a Mountain Lake Community

Applemoon is a dog-friendly 1960s log cabin nestled on an acre of the Blue Ridge Mountains. 2 bedrooms with Smart TVs, a porch with hanging daybed and bistro table, and a cozy game loft will give you plenty of space to relax. Outside, enjoy dinner on the huge deck or build a fire and don't forget to look up at the night sky! Applemoon strikes the perfect balance between rustic charm and comfort while maintaining your immersion in the peaceful mountain woodlands of Harpers Ferry.

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

Stoney Spring Overlook

This beautiful mountain farm home has breath taking scenic views of the surrounding Catoctin mountain. There are many nearby outdoor activities, including scenic hikes, mountain biking, Ski Liberty, wineries and the Catoctin zoo. While it is a peaceful get away in the mountains, it is just 30 minutes away from the Frederick, MD and historic Gettysburg, PA. Whether you want to get away from the city or explore more of Maryland, this is the perfect stay for you!