Holiday houses in Charles Town

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Top-rated holiday rentals in Charles Town

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Guest favourite

Chalet in Mercersburg

4.94 out of 5 average rating, 105 reviews

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.

Guest favourite

Home in Berkeley Springs

4.93 out of 5 average rating, 59 reviews

Serene Luxury Cabin, Mountainside Views, HOT TUB

Welcome to TreeTOP Breeze, our guests' favorite mountainside retreat! Proudly presented by Homegrown Hospitality, this cozy getaway offers a true taste of West Virginia charm. Nestled on 2 private wooded acres, this gem features 4 spacious bedrooms, 4 full baths, hiking trails, a private hot tub, a bumper pool table, and a cozy fireplace. Conveniently located just 5 miles from downtown Berkeley Springs, WV—ranked the #9 Small Town in America-it’s the perfect place to relax, unwind, and explore!

Guest favourite

Place to stay in Berkeley Springs

5 out of 5 average rating, 21 reviews

Unique A Frame: Hot Tub, Fire Pit, Cold Plunge

Step into this luxurious 3BR 2BA, A-Frame cabin built in 2024 and nestled in the tranquil area of Berkeley Springs, WV. Lounge in the stylish and radiant interior, soak in the hot tub on the deck, or explore "America's First Spa" and many Appalachian attractions and landmarks! ✔ Deck w/Hot Tub ✔ Fire Pit ✔ Cold Plunge ✔ Outdoor Dining ✔ Green Egg ✔ 3 King Bedrooms ✔ Open Design Living + Loft ✔ Full Kitchen ✔ Office ✔ Smart TV ✔ Wi-Fi ✔ Parking ✔ Community Pool, Tennis & Trails See more below!

Guest favourite

Cottage in Leesburg

4.91 out of 5 average rating, 374 reviews

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!

Guest favourite

Cabin in Great Cacapon

4.9 out of 5 average rating, 184 reviews

Cabin Getaway: Hot Tub ☆ Privacy ☆ Views

Welcome to this serene 1 bedroom, 1 loft, and 1 bath log cabin with gleaming hardwood floors, a cozy electric fireplace, a beautiful front deck with a firepit overlooking the forest, and a hot tub for ultimate relaxation. It's centrally located to Berkeley Springs, Cacapon State Park, and a variety of hiking, fishing, restaurants, and shopping. Enjoy the local attractions and breweries year round! Whether it's site-seeing or solitude, this unique cabin is a great retreat for your next getaway!

Superhost

Cabin in Berkeley Springs

4.87 out of 5 average rating, 154 reviews

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.

Guest favourite

Cottage in Middletown

4.91 out of 5 average rating, 254 reviews

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

Cozy cape in the ❤️ of Middletown, MD. Within walking distance 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

Guest favourite

Home in Hagerstown

4.93 out of 5 average rating, 57 reviews

Hot tub, Pool table+darts, near ski resorts

Your family will be close to everything when you stay at this centrally-located place. Quiet neighborhood and comfortable settings ** NO PARTIES ** Plenty of room to enjoy a getaway with friends and family without the headache of inconveniences. Basketball hoops on the driveway and pool side. Dart board and pool table offer indoor activities when the weather doesn't want to cooperate. Multiple HD t.v's for your viewing pleasure and HDMI connections to connect a gaming console of your choice.

Guest favourite

Home in Edinburg

4.98 out of 5 average rating, 374 reviews

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

Guest favourite

Cabin in Hedgesville

4.95 out of 5 average rating, 121 reviews

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

Guest favourite

Cabin in Harpers Ferry

4.97 out of 5 average rating, 144 reviews

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.

Superhost

Cabin in Harpers Ferry

4.8 out of 5 average rating, 420 reviews

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!