Holiday rentals with breakfast in Winchester

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Top-rated rentals with breakfast in Winchester

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

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Top guest favourite
A stone fireplace is centered in a rustic setting, featuring a stylish wrought iron screen. Flickering flames are visible, surrounded by two red lanterns and a glass of red wine beside an open bottle, creating a cozy ambiance for relaxing evenings.
Home in Marshall
4.99 out of 5 average rating, 116 reviews

Middleburg/Upperville-Stunning,renovated cottage

The Atoka House,a stunning 1801 log home on the historic register in Virginia hunt country.This 2-bedroom, 2.5 bath home with both upstairs and downstairs living rooms,is only 4 miles from Middleburg.Relax in the coziness of the log cabin, catch the spectacular sunsets from the deck and large fenced yard. Gas grill and outdoor firepit. Fireplace may only be used with a duraflame log(provided) for the safety of this historic home. Minutes from wineries, great meadow, polo and Upperville (UCHS)

Top guest favourite
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, 565 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

Guest favourite
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
4.95 out of 5 average rating, 114 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 a top-notch structure, 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 outdoor firepit and relaxing.

Top guest favourite
A cozy bedding arrangement is displayed with a variety of pillows in soft colors and patterns, including polka dots and checks. Above the bed, a wooden sign reads 'our nest is best,' adding a subtle decorative touch to the restful space.
Guest suite in Edinburg
4.99 out of 5 average rating, 456 reviews

Garage 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 favourite
The entrance features a welcoming porch area surrounded by colorful potted plants and flowers. A wooden rocking chair sits on the deck, complemented by a textured area rug. Double doors with grid-patterned glass provide access to the suite, framed by lush greenery.
Guest suite in Hagerstown
5 out of 5 average rating, 486 reviews

Oak Hill Private Suite Historic North End

A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Top guest favourite
The charming exterior of the cottage is shown, featuring a light-colored facade with multiple windows. A welcoming front door is visible, surrounded by vibrant flowers and greenery. A small stone walkway leads to a patio area with wooden seating, overlooking the lush yard.
Cottage in Bluemont
4.96 out of 5 average rating, 227 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 favourite
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, 200 reviews

The Hunt Box @ Tally Yo Farm

This is a residence above a 5-stall horse barn. A two bedroom house with 2 bath, Juliette balcony, great views, vaulted ceilings, fully appointed kitchen, laundry, 6 acre farm. Beautifully decorated in traditional English equestrian decor, with homage to the Northern Virginia hunts located just a stone's throw away. 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.

Top guest favourite
A modern studio space features large windows that allow natural light to fill the room. A cozy yellow chair sits beside a small coffee table, with a guitar resting on a stand nearby. The bed area is visible in the background, framed by a stylish shelf.
Guest house in Boston
4.99 out of 5 average rating, 206 reviews

The Bunkhouse- 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 bunkhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Guest favourite
Cabin in Great Cacapon
4.89 out of 5 average rating, 180 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 favourite
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, 420 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!

Top guest favourite
The exterior of a colonial era spring house showcases a natural stone base supporting a wooden structure. A spacious balcony with wooden railings extends from the second floor. Brightly colored hanging flower pots add a touch of greenery to the inviting façade.
Home in Blue Ridge Summit
4.99 out of 5 average rating, 593 reviews

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

Top guest favourite
A serene spring house is softly illuminated at dusk, set against a backdrop of a gradient sky. Ambient lights line the pathway leading to the house, while trees provide gentle framing of the scene.
Tiny home in Linville
4.99 out of 5 average rating, 740 reviews

The spring house at Thistle Hollow

Beautifully renovated spring house on the grounds of the 1800s Peter Breneman House. Soak up peace and quiet in one of the most beautiful corners of the Shenandoah Valley. Enjoy starry skies, sunrises, and birdwatching from your private porch. 9 minutes from Eastern Mennonite University, 13 minutes from James Madison University, and 45 minutes from the entrance to Shenandoah National Park.

Popular amenities for rentals with breakfast in Winchester

Quick stats about holiday rentals with breakfast included in Winchester

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹2,640 before taxes and fees

  • Total number of reviews

    150 reviews

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi