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.

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Top guest favorite
Farm stay in Elkton
4.98 out of 5 average rating, 169 reviews

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

Top guest favorite
A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.
Farm stay in Purcellville
4.98 out of 5 average rating, 223 reviews

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

Top guest favorite
Two black Adirondack chairs are positioned on a grassy area next to the river, offering serene views of the water and surrounding trees. Gentle sunlight filters through the leaves, creating a peaceful atmosphere for relaxation.
Cabin in Woodstock
4.96 out of 5 average rating, 139 reviews

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.

Top guest favorite
An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.
Cabin in Bluemont
4.99 out of 5 average rating, 611 reviews

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

Top guest favorite
Tiny home in Stephens City
5 out of 5 average rating, 120 reviews

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.

Top guest favorite
A quaint cottage is nestled in a lush green landscape, surrounded by colorful autumn trees. Rolling hills and the distant Blue Ridge Mountains form a scenic backdrop, with a clear sky above and soft sunlight illuminating the scene.
Tiny home in Free Union
4.96 out of 5 average rating, 171 reviews

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.

Top guest favorite
Guest suite in Edinburg
4.99 out of 5 average rating, 473 reviews

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.

Top guest favorite
The exterior of a red brick building is shown, featuring a striking peaked roof and multiple windows. A shaded porch is visible at the entrance, adorned with potted plants. Lush greenery surrounds the property, and a gravel path leads up to the structure.
Farm stay in Leesburg
5 out of 5 average rating, 121 reviews

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.

Top guest favorite
Four wooden outdoor chairs surround a circular stone fire pit, set on a grassy area. A stack of firewood is positioned nearby, and a window can be seen on the beige house exterior, accompanied by green foliage and colorful flowers in the background.
Cottage in Bluemont
4.96 out of 5 average rating, 244 reviews

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.

Top guest favorite
A colorful sunset fills the sky with hues of orange and pink, viewed from the property. The silhouette of the house is complemented by the warm light from the windows. Green foliage and flowers adorn the foreground, enhancing the serene atmosphere.
Guesthouse in Boston
4.97 out of 5 average rating, 233 reviews

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.

Guest favorite
Cabin in Great Cacapon
4.9 out of 5 average rating, 185 reviews

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

Top guest favorite
The exterior of a charming tiny home is displayed, featuring natural wooden siding and a metal roof. A small porch with wooden steps leads to a glass-paned front door. Potted plants adorn the entrance, while colorful flowering bushes are visible in the foreground.
Tiny home in Purcellville
4.97 out of 5 average rating, 463 reviews

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

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