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

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.

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.

Historic Springhouse Cottage @ Janney Family Farm.
Come for an escape to the country. Updated historic cottage is in a quiet country setting in the heart of the Shenandoah Valley, rural yet not remote. Enjoy a time of peaceful renewal. Relax overlooking the pastures and beautiful garden common space in the backyard retreat including a hot tub. Studio apartment with queen bed and additional futon sofa. Kitchenette is equipped with refrigerator, microwave, coffeemaker and dishes. Breakfast includes muffins, granola, and coffee.

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.

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.

Close, Spacious, Fully Furnished, Breakfast
Treat yourself to this fully furnished, spacious, clean and quiet apartment with breakfast items provided to start your day. Just 3 miles from Rt 81 and close to JMU, EMU, easy access to Shenandoah National Park, Massanutten Resort, Sentara Medical Center & shopping. Relax and refresh in a home-like atmosphere with a living room, well-stocked kitchen, study area, laundry, bedroom with a walk-in closet, and many amenities. Your comfort is our concern.

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!

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.

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 Winchester accommodations with breakfast
House rentals with breakfast

Treetop Retreat

West Park Gardens | Entire Property-4BR | Culpeper

Riverside Winter Escape – Hot Tub + Sauna + Games

Middleburg/Upperville-Stunning,renovated cottage

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

Charming Farmette-24cap/Pets OK-New Balt/Warrenton

Scenic Mountain

Historic 1840 Dr. Garrott House
Apartment rentals with breakfast

Rosemary's Nest LLC

Spacious Studio Retreat Private Entrance in Reston

The Engham Apartment at Before & After

come and stay at bird song hill

Trundle Private Suite Location Lily Garden BnB

Cozy Downtown Suite + Coworking (3S)

Two Bedroom Two Bathroom Massanutten Resort Stay

Secluded 1BR/1BA Massanutten mountain hideout
Bed and breakfast rentals with breakfast

The Hummingbird Room - Sparkling Stars Inn

Falling Creek - Rm #2

The Game Room at Mountain Home

Duck Inn B&B at Small Axe Farms

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

The Cottage at Dunthorpe Farm
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 $42 CAD 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

Wifi availability
20 of Winchester vacation rentals include wifi access

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

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with breakfast Virginia
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- Luray Caverns
- Stone Tower Winery
- Cunningham Falls State Park
- Whitetail Resort
- Shenandoah Valley Golf Club
- Gambrill State Park
- Cacapon Resort State Park
- Berkeley Springs State Park
- Bryce Resort
- Creighton Farms
- Robert Trent Jones Golf Club
- South Mountain State Park
- River Creek Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Bowling Green Country Club
- Reston National Golf Course
- Dinosaur Land
- Twin Lakes Golf Course
- JayDee's Family Fun Center
- Warden Lake
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Whiskey Creek Golf Club




