Holiday houses in Piney Mountain

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Top-rated holiday rentals in Piney Mountain

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Guest favourite
The Ordinary is surrounded by a spacious lawn, framed by trees and greenery. A small outbuilding is visible to the left, while the house features a welcoming porch and a pitched roof. Natural light brightens the exterior, emphasizing its classic Virginia charm.
Home in Barboursville
4.94 out of 5 average rating, 132 reviews

Historic 1790 House Near Charlottesville

Originally a tavern built 1790 in the Williamsburg style, the Ordinary sits 6/10 mile off the main road--no other house in sight. 22 miles from Shenandoah National Park, convenient to local vineyards, the Ordinary is set on 650 acres in conservation easement; solar energy; generator in event of power outage; outdoor fire pit; 2 great fireplaces; wood provided by owner. The house is over 200 years old with narrow, steep steps and may not be suitable for children and people with mobility issues.

Top Guest favourite
A charming cottage with a metal roof features a welcoming front porch, surrounded by greenery. Rocking chairs offer a cozy spot, while stone pathways lead to a landscaped yard. Light spills onto the deck from nearby trees, blending indoor and outdoor spaces harmoniously.
Home in Barboursville
4.93 out of 5 average rating, 294 reviews

Spaniel Hill; cozy hilltop home w privacy & views

Cozy hilltop with Views, deck and hot tub. Cottage furnished with original art and antiques collected by us, the cottage is easy to get to but feels like a world away. Recently renovated main level has three cozy bedrooms and 1.5 baths, sleeps 6, and the garden level suite offers one large king bed and a twin bed with full bath and separate sink area, sleeps 3. Close to UVA, Pantops 250 corridor, theDowntown Mall, Gordonsville and Orange to our north. Over 20 highly rated wineries within 20 m

Guest favourite
A charming cottage exterior showcases a green facade with textured wood siding, complemented by a welcoming porch. Outdoor seating is provided by rustic chairs around a fire pit on the lawn. A table nearby offers an inviting spot for dining, set against a backdrop of distant mountains.
Cottage in Crozet
4.9 out of 5 average rating, 230 reviews

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Top Guest favourite
A modern structure is nestled among tall trees, surrounded by lush greenery. The building features a dark exterior with large windows, allowing natural light to highlight the inviting entrance. Vibrant plants and foliage are visible in the foreground, enhancing the serene landscape.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 307 reviews

Renew @ Coniferidge.

Constructed in 2017 “ Renew” offers a peaceful, clean and simple space furnished with a comfortable modern mix style. It is situated a short distance from the main home and offers just the privacy you are looking for. This property, located outside beautiful Charlottesville Va. is an easy drive to restaurants, shopping, art, culture, wineries, history, parks and the Uva . Flat Screen Smart TV (use your logins to access your favorite sites ) NO pets - out of consideration of future guests

Top Guest favourite
The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.
Apartment in Somerset
4.99 out of 5 average rating, 206 reviews

Cozy Farm Apt near Cville•wineries, mt. views

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Top Guest favourite
The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.
Cabin in Free Union
4.99 out of 5 average rating, 205 reviews

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Top Guest favourite
A charming cottage is nestled among mature trees and vibrant landscaping, featuring a welcoming entrance. The rustic structure is complemented by lush greenery and seasonal foliage, emphasizing a serene, natural setting.
Guesthouse in Earlysville
4.97 out of 5 average rating, 380 reviews

Cottage at Frog Jump- woodland privacy at its best

Guesthouse ideal for two people. Small cottage (1 bed, 1 bath) is situated in a country setting on ten wooded acres along a large serene pond. It features a darling kitchenette with sink, fridge, microwave and toaster/convection oven. (No stove top, no oven.) You'll enjoy birdsong and views of various wildlife. A quiet, restful place to stay when you want to be near Shenandoah Nat’l Park, UVA, Charlottesville, Virginia wineries, Monticello, Montpelier, CHO, and other close-by attractions.

Top Guest favourite
A charming log cabin with a dark metal roof features a welcoming front porch adorned with potted flowers and decorative pumpkins. The rustic wooden door adds character, while the surrounding grassy area and trees provide a natural setting against a backdrop of distant mountains.
Cabin in Stanardsville
4.99 out of 5 average rating, 248 reviews

Cabin at Rabbit Hollow

Charming log cabin nestled in a glen by the Shenandoah National Park is an ideal retreat for a romantic get-a-way. The first floor contains a beautiful kitchen, dining area, full bathroom featuring a whirlpool tub, and cozy living room with a wood burning fire place. The second level holds the bedroom with a comfortable king size bed and a half bathroom. There are two porches where guests can relax with their morning coffee or evening cocktails while enjoying the wooded and mountain views.

Top Guest favourite
A rustic log cabin is surrounded by lush greenery in a serene wooded setting. The spacious front lawn is fenced, providing a safe area for pets. The porch features a swing, inviting relaxation amidst the natural landscape.
Cabin in Madison
4.97 out of 5 average rating, 119 reviews

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking

Bring the whole fur family & enjoy precious time away from the hustle & bustle of everyday life. This updated cabin sits on 12.5 acres of mainly wooded land in the heart of the blue ridge- Madison County. Within 30 minutes of wineries, breweries, hiking, & Charlottesville! Boasting a primary loft bedroom w/ a queen bed and a bonus room w/ a full bed, this home away from home can comfortably sleep 4-5! Front porch swing & fenced yard for the pups to play. Guests can completely relax!

Top Guest favourite
A spacious living area displays soft beige sofas paired with dark blue accent tables. Natural light filters through large windows, enhancing the warm, neutral tones of the walls. A glimpse of the kitchen and bedroom can be seen through open doorways, providing a sense of flow.
Home in Charlottesville
4.96 out of 5 average rating, 210 reviews

Woodwind Cottage

Woodwind Cottage is a brand new, beautifully built cottage with living room, bedroom, bath, kitchen and loft. It has charming architectural details and a covered porch for enjoying the view of the woods. The loft has a fold out sofa for an extra guest or private work space. The home has wifi, smart tv for streaming, and a gas fireplace. Enjoy reading in the oversized window seat, rise early to see deer in the yard or, perhaps, a hot air balloon overhead in the spring and fall.

Top Guest favourite
A grassy open area is depicted, with a black and white dog lying comfortably on the ground. In the background, several canoes are visible on a trailer, positioned under trees that provide partial shade.
Guest suite in Charlottesville
4.93 out of 5 average rating, 162 reviews

The Brothers Great Room

Your private guest suite is located in Northern Albemarle County Virginia. We cannot allow cats(due to family members with allergies and the extra cleaning required) We are just off of Route 29 with easy access to local venues. The suite is up one flight of stairs. Albemarle County is central to the University of Virginia, Monticello, Montpelier, wineries, craft beer breweries, and wedding venues in the area. Your dogs may run the open areas. Please clean up after your pet.

Top Guest favourite
An open living area is highlighted by a light-colored sofa and a wooden coffee table. A spiral staircase leads to an upper loft, while a dining table with wooden chairs sits nearby. Large windows provide ample natural light, illuminating the space.
Home in Charlottesville
4.98 out of 5 average rating, 595 reviews

The Loft at Minor Mill - Private loft apartment.

Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

Popular amenities for Piney Mountain holiday rentals