
Vacation rentals with breakfast in Winchester
Find and book unique breakfast rentals on Airbnb
Top-rated breakfast rentals 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

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.

Little Forest Tiny Cottages in Free Union
Enjoy the breathtaking views of the Blue Ridge Mountains on this 26 acre Olde English Babydoll Sheep farm right from your window. Our farm is a haven of peace and serenity in a secluded but centrally located area just 18 miles northwest of Charlottesville. Wake up to delicious farm fresh breakfast from our eco-friendly farm. Take pictures of fluffy sheep and angora rabbits grazing on rolling hills. Hike our private trail. Breathe in the fresh mountain airs. Sleep in. Slow down. Relax.

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.

The Cottage at Stonecroft
Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.

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!
Popular amenities for Winchester breakfast rentals
House rentals with breakfast

Riverside Winter Escape – Hot Tub + Sauna + Games

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Catoctin Comforts, Trails, & Tales

Scenic Mountain

The Enchanting Lavender House

Historic 1840 Dr. Garrott House

The Cottage at Oakland Green Farm

Cozy Orchard Home bike trail, hiking-dog friendly
Apartment rentals with breakfast

Spacious Studio Retreat Private Entrance in Reston

Modern One BR in a Great Location .

Charming Quiet Spacious Well Furnished Closeby Apt

Your own apartment to use in a tranquil setting

come and stay at bird song hill

Trundle Private Suite Location Lily Garden BnB

Cozy Downtown Suite + Coworking (3S)

Lovely Lower Level 2 Bedroom Suite - Dog Friendly
Bed and breakfast rentals with breakfast

The Hummingbird Room - Sparkling Stars Inn

Falling Creek - Rm #2

Quilt Room

The Game Room at Mountain Home

Farm Cottage just outside town of Orange.

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

Eisenhower Suite at Olinger House

Step Back in Time at Timberwinds Cabin
Quick stats about vacation rentals with breakfast included in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at €35 per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Winchester vacation 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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- Rentals with breakfast Virginia
- Rentals with breakfast United States
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Berkeley Springs State Park
- Cunningham Falls State Park
- Jiffy Lube Live
- South Mountain State Park
- Harpers Ferry National Historical Park
- Cacapon Resort State Park
- Gambrill State Park
- Shenandoah River Outfitters
- Hollywood Casino At Charles Town Races
- Whitetail Resort
- Rock Gap State Park
- Green Ridge State Forest
- Shenandoah Caverns
- Reston Town Center
- Weinberg Center for the Arts
- Antietam National Battlefield
- Sky Meadows State Park
- Big Cork Vineyards
- Skyline Caverns
- Bluemont Vineyard
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