Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Chalet in Mercersburg

4.94 out of 5 average rating, 112 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

Cabin in Basye

4.87 out of 5 average rating, 111 reviews

Gorgeous Cabin | Hot Tub & Mountain Views!Ski Golf

Escape to our cozy, spacious 3-bedroom retreat with a loft, minutes from Bryce Resort. Enjoy stunning mountain views and a 6-person hot tub! 🩳👙 This private mountain setting is perfect for an adventurous or relaxing trip to the Shenandoah Valley. The loft includes a pullout bed for extra guests. Whether you're here to ski, hike, mountain bike, snowboard, kayak, snowshoe, or simply relax and escape city life, you'll find everything you need. Enjoy a complimentary bottle of wine on arrival. 🍷

Guest favourite

Home in Basye

4.93 out of 5 average rating, 161 reviews

Romantic Treetop Retreat: Hot Tub•King Beds

Brand New Listing! Completely renovated cabin sits up among the trees. This comfy and stylish cabin is the perfect place to visit Bryce Resort (1.5 miles) and the many wineries and hikes nearby. The hot tub is the ideal spot to relax and breath the mountain air. Multiple outdoor spaces and fire table to enjoy. New Memory Foam beds, 65 inch Tv over the electric fireplace, rainfall shower head, stocked kitchen Every inch of the house has been designed for the perfect romantic or family getaway.

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 Basye

4.99 out of 5 average rating, 195 reviews

“Lazy Basye” Mountain Resort Cabin - Hot tub, 4BR

Bryce Resort (ski/golf/lake/bike park) in the Shenandoah! Ideal setup- 2 indoor living spaces! 4 BR/3 full bath. Fully equipped kitchen, memory foam mattresses (2 king/1 queen/2bunks), electric fireplace, hot tub, outdoor fire pit, screened porch w/ dining/sectional/TV. Gas grill, deck dining & views! Rec room w/ views, pool table, foosball, Golden Tee, 65" TV, sectional, games! Multiple decks/patio, fast WiFi, private parking, full size W/D, 4 smart TVs. Must be 25 to book. Holidays-3 night min

Guest favourite

Home in Elkton

4.95 out of 5 average rating, 185 reviews

Hottub 5 acres, Great hiking,The best views around

Stony Creek Lookout is a one-of-a-kind luxury retreat perched in the serene seclusion of the mountains.Brand new complete renovation, modern amenities, hot tub, sizable elevated deck, video/board games, theatre room, kayaks and high quality furnishings !This extraordinary stay adjoins the Shenandoah NatlPark with the best views in the Shenandoah Valley, hike out your back door. Pet friendly, 5 min from Massanutten 4 season resort, Shenandoah River & much more. Great Wifi & cell service! 5 TVs

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!

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

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.

Guest favourite

Cottage in Shenandoah

4.96 out of 5 average rating, 184 reviews

Cozy Cottage Retreat: SNP, Luray Caverns, River

Clean & cozy cottage conveniently located in the town of Shenandoah. Guest love the central location to Shenandoah National Park via Elkton Swift Run (12 miles) or Luray Thornton Gap (28 miles), Luray Caverns (15 mi), Massanutten Resort (9 mi), and a short drive to local colleges like JMU, EMU, and Bridgewater College. Walking distance to Shenandoah River, a public boat landing, local stores and small parks. Please check out our reviews to see what guest have to say.

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, 164 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.