Holiday rentals in Upperville

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Top-rated holiday rentals in Upperville

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Guest favourite

Cabin in Luray

4.9 out of 5 average rating, 188 reviews

1850's Massanutten Spgs -"Charmed by the Ambiance"

Enjoy a taste of time travel from the 21st century to the 19th century while vacationing in style at our exquisitely restored 1850's cabin. Our cabin is walking distance to Massanutten Boat Landing (motor boating) and our private fishing pond. Fine restaurants, vineyards, whiskey Distillery, and horse back riding are just minutes away. The Cooter's Museum is just 2.4 miles from our cabin. Luray Caverns and Museum just 12 min - Shenandoah National Park is 20 min, G W National Forest is close by.

Guest favourite

Cabin in Luray

4.94 out of 5 average rating, 152 reviews

❤️️Wildflower Cabin❤️️ A Luxury Riverfront Retreat

*Come in and relax in this tranquil, peaceful hideaway. *Newly renovated cabins on Shenandoah River. *100 feet riverfront on a 2 acre property *AC/heat, satellite Wifi, fresh linens, towels, DVDs, board games. *Full kitchen w/ utensils, microwave, toaster, K-cups. *Secluded, close tohiking, caverns, wineries, and river adventures.*Dog friendly (extra fee of $40/dog/stay and will be asked for after booking, not included in booking fees) ! *King-size bed in bedroom, queen sofa bed in living room.

Guest favourite

Cabin in Shenandoah

4.92 out of 5 average rating, 374 reviews

Romantic Cozy Cabin Firepit, Grill & Wi-Fi

Embrace the endless beauty of the Shenandoah Valley from this private mountain retreat with stunning sunset views and endless stars. Enjoy the community's private access to the Shenandoah River. Escape the city, but still have access to our modern comforts of cell phone service and WIFI. Relax in front of the wood-burning fireplace. or just enjoy reading a book on the swing in the screened porch. Our property has one security camera and noise monitoring at the entry area of the front door.

Top guest favourite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 109 reviews

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!

Guest favourite

Cabin in Stanley

4.97 out of 5 average rating, 182 reviews

Stunning Mountain Views in Luxurious Log Home!

Perfect for couples or families wanting STUNNING MOUNTAIN VIEWS (from the cabin & from the hot tub) in the ideal location. Romantic, luxurious & immaculately clean custom cabin, fully equipped w/all pine interior. Super close to Shen Natl Park/Skyline Drive, Luray Caverns, unique shops & markets, restaurants, horseback riding, fishing, golf, wineries/breweries, historic sites, Shenandoah River, Lake Arrowhead & the slopes of Massanutten Resort! Find us at LURAY MOUNTAIN CABINS for SPECIALS!

Top guest favourite

Home in Edinburg

4.98 out of 5 average rating, 395 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.

Superhost

Cabin in Shenandoah

4.79 out of 5 average rating, 466 reviews

Shenandoah Sunsets~Breathtaking Views~ New Hot Tub

*Weekends fill fast, but we have great weekday rates! --Breathtaking mountain top cabin with private river access • 180 degree sunset views from 4 decks • Minutes from downtown Luray & Massanutten Resort • Backs to 400 acres of private woodlands • Fully equipped & stocked kitchen • Gas Fireplace • Grill • Onsite washer & dryer • Queen sofa bed • Foosball table • Satellite internet • Smart TVs • Paved driveway • Extensive DVD collection + games • Come feel the amazing mountain top breezes

Superhost

Guest suite in Warrenton

4.93 out of 5 average rating, 121 reviews

Lakeside 2-Bedroom Suite

Waiting to welcome you to our treasured peaceful lakeside living. Hot tub, swimming pool and canoe available to complete a family adventure. Two bedrooms joining a bath (more suitable for children and parents or 2 cozy couples); private sunny living room overlooking gardens and bird sanctuary on lake. Fish from property or by our canoe. Friendly, quiet suburb in beautiful Virginia countryside, but one hour drive to Washington DC for city life and adventures. Relaxation at its best!

Top guest favourite

Cottage in New Market

4.98 out of 5 average rating, 128 reviews

Lakeside, fishing, fire pit, swimming, coffee bar

PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

Superhost

Cabin in Harpers Ferry

4.81 out of 5 average rating, 436 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!

Guest favourite

Cabin in New Market

4.91 out of 5 average rating, 165 reviews

Sunset Views! Hot Tub! Fireplace! Mountain Escape

Experience the ultimate mountain retreat in Newmarket, VA!! Enjoy spectacular views of the valley from the deck's hot tub or relax on the beautiful screened porch. The interior has been completely remodeled, featuring a wood-burning stove and high-speed internet. Surrounded by the George Washington National Forest on three sides, adventure awaits just steps away. Book your stay today and immerse yourself in the tranquility of the mountains. 4WD/AWD required.

Guest favourite

Cabin in Rileyville

4.94 out of 5 average rating, 148 reviews

A+ Privacy & Views | HotTub + Firepit + BBQ | Pets

Secluded mountain cabin with 2 kings, hot tub, fire pit & panoramic views! ★ "Amazing place… the views are breathtaking." ☞ 2 level deck w/ mountain views ☞ Complimentary SUV provided ☞ Hike to waterfall (20 mins) ☞ Fully equipped + stocked kitchen ☞ Patio w/ BBQ grill + dining ☞ 50” Smart TV w/ Netflix ☞ Indoor wood fireplace ☞ Pet friendly* 20 mins → DT Luray (cafes, dining, shops) 30 mins → Shenandoah National Park