Holiday rentals with breakfast in Winchester

Find and book unique Holiday Accommodation with Breakfast on Airbnb

Top-rated Holiday Accommodation 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 vibrant garden features a variety of flowers and lush greenery, showcasing colors like red, purple, and yellow. The farmhouse, with its white exterior, is framed by trees and mountains in the background, creating a serene outdoor setting.
Farm stay in Elkton
4.98 out of 5 average rating, 165 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 favourite
A spacious pool area is framed by carefully landscaped greenery and stone paving. Beyond the pool, expansive fields dotted with trees and a charming barn are visible. Fencing lines the property, contributing to the serene rural setting.
Farm stay in Purcellville
4.98 out of 5 average rating, 220 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 favourite
A rustic building with a wooden exterior and a red metal roof is set amid lush greenery. A large window beside an entry door is framed by flowering plants, while a stone pathway leads toward a well-maintained lawn and seating area.
Loft in Harpers Ferry
4.92 out of 5 average rating, 225 reviews

Carriage Suite Location Private Lily Garden BnB

A completely equipped two bedroom vacation rental suite. Located in the Historic District of central Harpers Ferry. The Carriage House is a large unit with private entrance, two beds, full bathroom, and kitchen. The shared yard has a picnic table and swing to enjoy the summer weather. There's internet access & cable television. A good breakfast is included! Come tour American History, hike the Appalachian Trail, bike the C&O Canal, see nature's wonders, and access Washington DC by commuter rail.

Top 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
4.96 out of 5 average rating, 136 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 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, 606 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 favourite
Tiny home in Stephens City
5 out of 5 average rating, 112 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 favourite
Guest suite in Edinburg
4.99 out of 5 average rating, 471 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 favourite
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, 116 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 favourite
The cabin features a welcoming front porch with a pair of white rocking chairs, providing a comfortable spot to relax. Wooden steps lead up to the porch, embraced by lush greenery and ferns, enhancing the cabin's secluded and natural setting.
Cabin in Culpeper
4.97 out of 5 average rating, 214 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Top Guest favourite
A Scandinavian-inspired cabin is nestled among lush greenery, featuring a modern wooden exterior with large windows that invite natural light. The elevated structure sits on a gentle slope, providing a serene view of the surrounding trees and grass.
Cabin in Shenandoah
4.99 out of 5 average rating, 184 reviews

Modern Nordic cabin w/ sauna, ideal for couples

This Scandinavian-inspired cabin provides a serene retreat nestled in the trees, ideal for couples and solo getaways. Enjoy relaxing in the barrel steam sauna, cozy up to a fire, and explore forest hikes just minutes down the road. Perfectly located nearby all that the Shenandoah Valley has to offer, including Shenandoah National Park, George Washington National Forest, wineries, water adventures, and charming local towns. Welcome to Big Meadows @ Roaring Run Cabins.

Guest favourite
A modern Scandinavian-inspired cabin is set against a backdrop of lush greenery, complemented by a private barrel steam sauna nearby. The property features a wooden deck leading to the entrance, with a pathway of stepping stones leading through the vibrant grass.
Cabin in Shenandoah
4.98 out of 5 average rating, 187 reviews

Stunning Scandi cabin w/ sauna near Shenandoah NP

This Scandinavian-inspired cabin provides a serene retreat nestled in the trees, perfect for couples and solo getaways. Enjoy relaxing in our barrel steam sauna, cozy up to a fire, and explore hikes just minutes down the road. Perfectly located nearby all that the Shenandoah Valley has to offer, including Shenandoah National Park, George Washington National Forest, wineries, water adventures, and charming local towns. Welcome to Rapidan @ Roaring Run Cabins.

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.
Guesthouse in Boston
4.97 out of 5 average rating, 231 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.

Popular amenities for Winchester Holiday Accommodation with Breakfast

Quick stats about holiday rentals with breakfast included in Winchester

  • Total holiday rentals

    Explore 20 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winchester holiday 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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