
Vacation rentals with breakfast in Winchester
Find and book unique breakfast rentals on Airbnb
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 €26 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

4.7 Average rating
Winchester stays receive an average rating of 4.7 out of 5 from guests
Top-rated breakfast rentals in Winchester
Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

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 acre with access to wooded a trail leads to 5 small 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
4.99 out of 5 average rating, 640 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
4.98 out of 5 average rating, 243 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.
4.96 out of 5 average rating, 149 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.
5.0 out of 5 average rating, 170 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.
4.99 out of 5 average rating, 487 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.
5.0 out of 5 average rating, 149 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.
4.97 out of 5 average rating, 260 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.
4.98 out of 5 average rating, 240 reviews
Private Log Cabin, Fiber WiFi, Lots of Wildlife!
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
4.89 out of 5 average rating, 191 reviews
The Cottage at Dunthorpe Farm
The Cottage is a restored wagon barn nestled against the Blue Ridge Mountains. You'll enjoy quality, comfort, quietude, and pastoral views. We are a fully licensed and inspected B&B on a 1790's farm in rural Loudoun County VA. Each morning you are treated to a continental breakfast of fresh pastry, fruit sourced from local farms, and homemade jams which we quietly deliver by 7:30 unless otherwise requested. Base price is for 1-2 people.
4.99 out of 5 average rating, 270 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!
4.97 out of 5 average rating, 483 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.
4.99 out of 5 average rating, 680 reviewsPopular amenities for Winchester breakfast rentals
House rentals with breakfast

More Luxury = Gym + Entertainment + Best Location
4.94 out of 5 average rating, 215 reviews
Huge Private Wooded Estate 5BR/3BA in Manassas, VA
4.81 out of 5 average rating, 159 reviews
Romantic Getaway-Heated Spa - Seasonal Pool!
4.98 out of 5 average rating, 206 reviews
The Dacha. Rebirth sauna experience
4.91 out of 5 average rating, 114 reviews
The Cottage at Oakland Green Farm
4.98 out of 5 average rating, 64 reviews
Lee Ridge Mtn Retreat– 3BR/Hot Tub/Pet/ RampAccess
5.0 out of 5 average rating, 15 reviews
Riverside Winter Escape – Hot Tub + Sauna + Games
5.0 out of 5 average rating, 9 reviews
Charming: The perfect setting for a memorable stay
4.93 out of 5 average rating, 61 reviewsApartment rentals with breakfast

Trundle Private Suite Location Lily Garden BnB
4.85 out of 5 average rating, 168 reviews
come and stay at bird song hill
4.89 out of 5 average rating, 76 reviews
The Engham Apartment at Before & After
4.98 out of 5 average rating, 91 reviews
Beautiful Private Suite + Coworking Downtown (3N)
4.94 out of 5 average rating, 34 reviews
Nirvana private aptmnt. w/kitchen+laundry (No fees)
4.74 out of 5 average rating, 158 reviews
Light Horse Inn: Suite 1 Breakfast Included
4.88 out of 5 average rating, 33 reviews
Peaceful Private Downtown + Coworking (2S)
5.0 out of 5 average rating, 47 reviewsBed and breakfast rentals with breakfast

Step Back in Time at Timberwinds Cabin
4.95 out of 5 average rating, 300 reviews
Apple B&B’s Pristine Suite
4.97 out of 5 average rating, 125 reviews
The Game Room at Mountain Home
4.95 out of 5 average rating, 185 reviews
Pet-Friendly Private Suite With Luxury Breakfast
4.99 out of 5 average rating, 125 reviews
Guest Suite w/ Homemade Breakfast & Country Charm!
4.98 out of 5 average rating, 123 reviews
Redwood suite - Loudoun Valley Manor
5.0 out of 5 average rating, 21 reviews
Private Room in Historic B&B 2 Blocks from the C&O
4.96 out of 5 average rating, 25 reviews
River Retreat Suite- Breakfast for 2
5.0 out of 5 average rating, 7 reviewsDestinations to explore
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