Holiday houses in Brightwood

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Top-rated holiday rentals in Brightwood

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Top Guest favourite
Apartment in Madison
4.91 out of 5 average rating, 264 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Top Guest favourite
The log cabin exterior is showcased, featuring a welcoming front porch with wooden railings. Stairs lead up to the entrance, flanked by natural stone landscaping. Surrounding trees create a serene atmosphere, while warm lighting from the windows adds a cozy touch.
Guest suite in Reva
4.97 out of 5 average rating, 143 reviews

The Log Cabin at Ridgeview - Hiking, Wine, UVA

Entire main floor of quaint log cabin in the heart of Virginia's Wine Country. Close to Charlottesville airport, UVa campus, Shenandoah National Park, wineries, breweries, local restaurants. NOTE: Prices shown are for 2 bedrooms, 1 queen and 1 double, and 2 baths. For access to 3rd bedroom, at an additional fee which includes one double and one single, set number of guests to 5 or 6. Access to laundry. Cozy front porch, tons of parking, screened in porch out back for dining or relaxing.

Top Guest favourite
Apartment in Gordonsville
4.97 out of 5 average rating, 502 reviews

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of the historic district of Gordonsville. No box stores here, just quaint shops and restaurants. The apartment is right on Main Street nestled in the middle of boutique shops and brick sidewalks with Monticello, Montpelier, the University of Virginia, Shenandoah National Park, local vineyards and many historic sites near by. This is a private second story apartment above a local business with a separate entrance and key-less entry.

Top Guest favourite
A living area features a comfortable gray sofa and armchair, set on a light area rug. A wooden coffee table is centrally located, while a TV sits on a decorative stand. Natural light enters through a window, complemented by soft lighting from a chandelier above.
Cottage in Orange
4.95 out of 5 average rating, 477 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Top Guest favourite
A cozy living area is equipped with a vibrant yellow armchair and a light gray sectional sofa. A large screen TV is mounted on the wall, and natural light enters through a window adorned with white curtains. A round wooden coffee table sits on a patterned area rug.
Apartment in Culpeper
4.98 out of 5 average rating, 125 reviews

Red Fox Retreat

Easily walkable to Downtown Culpeper! This restored and newly renovated historic property allows easy access to Downtown Culpeper. It features a large outdoor fire pit and expansive grounds to spread out and relax. This 1000 sqft unit is located in the upper level with views of the surrounding grounds and trees. Brightly decorated and designed in partnership with Lets Go and Stay properties; the Red Fox retreat is a great place to stay while visiting Culpeper and the surrounding area.

Top Guest favourite
The yurt is set against a starry night sky, surrounded by towering trees. A spacious deck leads to the yurt's entry, while warm light emanates from its windows. The scene showcases a natural ambiance highlighted by foliage and a gravel path leading to the entrance.
Yurt in Etlan
4.96 out of 5 average rating, 248 reviews

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

Guest favourite
An open-plan kitchen and living area is showcased with wooden beams and large windows, allowing natural light to illuminate the space. A kitchenette features wooden cabinetry, a microwave, and a small dining bar with three tall stools. A rocking chair is positioned beside a window overlooking the woodland.
Farm stay in Brightwood
4.94 out of 5 average rating, 155 reviews

Robinson River Cabin - Tri Creek Farm

If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.

Guest favourite
A welcoming living room features a cozy sectional sofa and a yellow accent chair, complemented by a clear coffee table. Natural light enters through two windows draped with patterned curtains. Decorative items include a mirror, wall art, and a soft throw blanket on the sofa.
Home in Culpeper
4.95 out of 5 average rating, 467 reviews

Cute Home in Downtown Culpeper with many extras!

Enjoy our recently updated home in downtown Culpeper. Our small home sits in a prime location within 1-3 blocks of amazing restaurants, breweries, and interesting shops.The house is located in a safe and quiet part of town. Convenient distance from Blue Ridge Mountain hiking. This property is professionally cleaned and sanitized after each reservation. Perfect for a family getaway! We are now accepting longer-term reservations. Top-rated accommodation in Culpeper for 2018-2022

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.
Guesthouse in Boston
4.99 out of 5 average rating, 219 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.

Guest favourite
A small, rustic cabin is set amidst a lush green landscape, framed by trees. The cabin features a front porch with a green door and a chimney, surrounded by a well-maintained grassy area. Natural light filters through the foliage, creating a serene atmosphere.
Guesthouse in Syria
4.87 out of 5 average rating, 690 reviews

Cozy 1 room cabin in the mountains.

In the heart of the Shenandoah mountains. 1 mile from White Oak Canyon and Old Rag for amazing hikes. Perfect for the fly fisherman (lots of local streams) or a nice quiet get-away for a couple. Once you park your car you can sit back and just listen to the river flowing in the back yard & enjoy a nice beverage next to the fire pit. The property is a very special place! UPDATE: New kitchen counters and new table and chairs

Top Guest favourite
A spacious living area is furnished with a patterned sectional sofa adorned with decorative pillows. A central coffee table sits on a soft carpet. Natural light fills the room through large windows, while a ceiling fan adds comfort to the inviting space.
Chalet in Brightwood
4.97 out of 5 average rating, 161 reviews

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet

Top Guest favourite
Apartment in Charlottesville
4.97 out of 5 average rating, 432 reviews

2 King/1 Twin Near Downtown & UVA

⭐️Two bedroom lower-level apartment (2 king beds, 1 twin XL, 1 toddler bed, 1 pack-n-play) in a quiet neighborhood near downtown! ⭐️Our guests rave about the excellent value, amenities, & cleanliness! 📍1 mile from UVA Hospital and Downtown Mall 📍1.6 miles from UVA ⭐️No smoking! ⭐️Please read note about the slope to the entrance 🟢The person booking must be present during the stay

Popular amenities for Brightwood holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Madison County
  5. Brightwood