Holiday rentals with breakfast in Winchester

Duck Inn B&B at Small Axe Farms

Unique private space on our small family farm. Relax on our large deck, walk our property, or explore the local area. Option to add homecooked breakfast and dinner. Great location : 8 mi to Massanutten (snow sports, arcade, golf, waterpark, mountain biking); 5 mi to Shenandoah Nat'l Park (hike, scenic cycling/drive); 4 mi to Shenandoah River (fish, kayak, rafting, tubing); 3 mi to Elkton (award-winning brewery, excellent local restaurants, and shops); 20 mi to JMU, 35 mi to Charlottesville/UVA

The Hunt Box @ Tally Yo Farm

Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

Rivah Retreat, HotTub~Firepit-Fishing-Deck-Private

Rivah Retreat is a one-of-a-kind luxury getaway tucked away on the pristine North Fork of the Shenandoah River. An expansive retreat and custom cabin spread over six acres of riverfront property located just 90 minutes from the White House. With modern amenities, hot tub, gas fireplace, spacious elevated deck, board games, movies, and so much more! Enjoy fly fishing from the private riverbank, quiet walks, abundant wildlife, smores at the firepit and relaxing. The property is best for adults.

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities-4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by! These are rustic not luxurious Cabins

Farm Stay in a luxury tiny home with hot tub

Welcome to “Horsefeathers” a tiny home on an historic property where you will be immersed in a farm experience! Although tiny, this house is equipped with all top of the line luxuries to include a personal hot tub, an automatic cappuccino maker, a king nectar mattress-just to name a few. Only minutes to Winchester the location is convenient to restaurants and shopping yet you’ll feel like you have been transported back in time to a working homestead where you can interact with all the animals.

The Haven, a cozy cabin in the woods. Pet friendly

Nestled in the forest, surrounded by beauty. Ideal for a weekend getaway or extended vacation, the cabin features a covered porch, large yard, and firepit—perfect for outdoor relaxation. Cozy up by the fireplace after a day of exploring nearby hiking trails, creeks, and breathtaking views. Just 15 minutes from Harrisonburg and JMU, and only a few minutes from Riven Rock Park and Switzer Lake, this cabin offers easy access to hiking, fishing, and all the natural wonders Virginia has to offer.

Private Apartment, King Bed, Easy access to I-81

Our home is located in the heart of the beautiful Shenandoah Valley . Close to historic towns, Civil War battlefields, wineries, breweries, distilleries & hiking trails. Access to Shenandoah National Park/Skyline Drive's Thornton Gap entry is 40 miles from Edinburg. Shenandoah Caverns is minutes away & Luray Caverns is 35 minutes away. Less than 35 minutes from JMU & EMU. Easy 2 minutes access to Interstate I-81. Pets: Case-by-Case. Due to allergies "No Cats". See instructions below.

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

Stunning Scandi cabin w/ sauna near Shenandoah NP

This Scandinavian-inspired cabin provides a serene retreat nestled in the trees, perfect for couples and solo getaways. Enjoy relaxing in our barrel steam sauna, cozy up to a fire, and explore hikes just minutes down the road. Perfectly located nearby all that the Shenandoah Valley has to offer, including Shenandoah National Park, George Washington National Forest, wineries, water adventures, and charming local towns. Welcome to Rapidan @ Roaring Run Cabins.

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Beautiful Log Cabin in Private WV Mountains

We love our private log cabin set far back from the gravel road, deep in the West Virginia mountains. 20 min from Berkley Springs, 3 min drive to the river w/ private access & 2 hours from DC / Baltimore. - The log cabin style is spectacular - Gigabit Fiber Wifi & ethernet - Sit/Stand desk w/ 27" 4k monitor - 42" TV w/ roku ultra & blu-ray - Game table w/ board games - Infant & Toddler friendly - Super dog friendly - Fire pit, grill & fireplace

Tiny House near Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch with private parking. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!