
Holiday rentals with breakfast in Winchester
Find and book unique Holiday Accommodation with Breakfast on Airbnb
Top-rated Holiday Accommodation with Breakfast in Winchester
Guests agree: These breakfast rentals are highly rated for location, cleanliness and more.

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

Carriage Suite Location Private Lily Garden BnB
A completely equipped two bedroom vacation rental suite. Located in the Historic District of central Harpers Ferry. The Carriage House is a large unit with private entrance, two beds, full bathroom, and kitchen. The shared yard has a picnic table and swing to enjoy the summer weather. There's internet access & cable television. A good breakfast is included! Come tour American History, hike the Appalachian Trail, bike the C&O Canal, see nature's wonders, and access Washington DC by commuter rail.

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.

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.

Comfortable and unique 1790's log cabin
Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Modern Nordic cabin w/ sauna, ideal for couples
This Scandinavian-inspired cabin provides a serene retreat nestled in the trees, ideal for couples and solo getaways. Enjoy relaxing in the barrel steam sauna, cozy up to a fire, and explore forest 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 Big Meadows @ Roaring Run Cabins.

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.
Popular amenities for Winchester Holiday Accommodation with Breakfast
Holiday House Rentals with breakfast

Riverside Winter Escape – Hot Tub + Sauna + Games

Bull Run Mountain Retreat

Lee Ridge Mtn Retreat– 3BR/Hot Tub/Pet/ RampAccess

Middleburg/Upperville-Stunning,renovated cottage

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Catoctin Comforts, Trails, & Tales

Historic 1840 Dr. Garrott House

The Cottage at Oakland Green Farm
Apartment rentals with breakfast

Spacious Studio Retreat Private Entrance in Reston

Charming Quiet Spacious Well Furnished Closeby Apt

Trundle Private Suite Location Lily Garden BnB

Your own apartment to use in a tranquil setting

come and stay at bird song hill

Cozy Downtown Suite + Coworking (3S)

Beautiful Private Suite + Coworking Downtown (3N)

Big views! - The Loft at Wildwood
Bed and breakfast rentals with breakfast

The Hummingbird Room - Sparkling Stars Inn

Redwood suite - Loudoun Valley Manor

Falling Creek - Rm #2

The Game Room at Mountain Home

River Retreat Suite- Breakfast for 2

Private Room in Historic B&B 2 Blocks from the C&O

Step Back in Time at Timberwinds Cabin

Apple B&B’s Pristine Suite
Quick stats about holiday rentals with breakfast included in Winchester

Total holiday rentals
Explore 20 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $56 AUD per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.6 Average rating
Winchester stays receive an average rating of 4.6 out of 5 from guests
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- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Berkeley Springs State Park
- Cunningham Falls State Park
- Harpers Ferry National Historical Park
- Jiffy Lube Live
- South Mountain State Park
- Cacapon Resort State Park
- Shenandoah River Outfitters
- Whitetail Resort
- Hollywood Casino At Charles Town Races
- Green Ridge State Forest
- Reston Town Center
- Rock Gap State Park
- Sky Meadows State Park
- Antietam National Battlefield
- Weinberg Center for the Arts
- Skyline Caverns
- Dulles Town Center
- Bluemont Vineyard
- Shenandoah Caverns
- Old Town Winchester Walking Mall
- Museum of the Shenandoah Valley





