Vacation rentals in Castleton

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Top-rated vacation rentals in Castleton

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Top guest favorite

The exterior of the tiny house is shown, featuring a light-colored siding and several windows that allow natural light inside. A wooden deck with steps leads to the entrance, and a fenced area provides privacy. Lush greenery surrounds the home, adding a natural backdrop.

Tiny home in Culpeper

4.98 out of 5 average rating, 115 reviews

3 Bed Tiny House in Culpeper w/ Kitchen & Firepit!

Welcome to our cozy tiny house in Culpeper, VA! This is the perfect retreat for couples/small groups looking for a unique & memorable experience. W/ open 2 lofts & a pull out couch this home sleeps up to 6 guests. The fully equipped kitchen allows for easy cooking. The composting toilet is an eco-friendly alternative w/o giving up convenience. Enjoy the outdoor fire pit & lounge area or visit some of the nearby attractions like Shenandoah National Park, shops downtown, & Death Ridge Brewery!

Top guest favorite

An A-frame cabin is set against a backdrop of vibrant autumn foliage. The cabin features a textured dark exterior and a welcoming orange front door. Neatly lined stone steps lead to the entrance, surrounded by landscaped gardens and seasonal decorations.

Cabin in Etlan

4.99 out of 5 average rating, 160 reviews

Modern Mountain Cabin w/WiFi, TV, Fire Pit,Patio

Come escape to our cozy retreat amidst the stunning beauty of the Shenandoah National Park region. Our unique 400 sq ft tiny home offers all the modern amenities, fully equipped kitchen, private patio w/ fire pit, loft bedroom , and spacious bathroom. Only minutes from Old Rag Mountain, wineries, breweries, horseback riding, trout fishing, and more. Unwind & relax after a day of exploring on your spacious patio.Are your desired dates already booked? Check out our other listing, Bald Eagle Cabin.

Top guest favorite

A historic log cabin is set on a grassy expanse, with a red metal roof contrasting against the wooden logs. The porch area features a small table and chairs, surrounded by trees and farmland. Horses are visible in the background, enhancing the rural setting.

Farm stay in Rixeyville

4.97 out of 5 average rating, 293 reviews

Historic Tiny Log Cabin at Beechwood View Farm

Enjoy the beauty of each season at our historic Tiny Log Cabin, built in the 1800s and newly renovated on a beautiful farm setting. Please read all of the description below, and scroll to the bottom before booking! Note—the cabin can be warm in the summer and chilly in the winter due to the logs and chinking. There is a window unit AC and heater in the winter. Also note—the full restroom/shower is a 30 yard walk to the basement of our home. Kuerig with coffee. No refrigerator or microwave.

Guest favorite

The exterior of the country house showcases a rustic red façade complemented by a covered front porch. A welcoming entryway is flanked by lush greenery and a gravel driveway, evoking a serene rural atmosphere amid the surrounding trees.

Cabin in Reva

4.94 out of 5 average rating, 161 reviews

10-Acre Dog-Friendly House w Grill & Near Wineries

Welcome to the Reva Retreat! This country house sits on 10 acres, nestled between Shenandoah Nat'l Park & the Blue Ridge Mtns, with wineries and breweries nearby. Approx 1.5 hours from DC and 45 mins from Charlottesville makes this the perfect getaway destination to escape the city & unplug. Stocked with amenities: BBQ grill, dine al fresco, stargaze by the firepit, cook a feast in the new kitchen, play board games in the basement, or connect your laptop to a 32" monitor to work remotely.

Top guest favorite

A rustic cabin is illuminated by warm golden light from its windows, set against a soft twilight sky. The log exterior reflects the vintage charm of the structure, while the surrounding trees create a serene atmosphere, inviting guests to relax on the front porch.

Place to stay in Bentonville

4.99 out of 5 average rating, 474 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

Guest favorite

A welcoming wreath is displayed on a white door, featuring lavender flowers interspersed among green foliage. A sign in the center reads 'Welcome to Treetop at Mt Run Lake,' adding a personal touch to the entrance.

Apartment in Culpeper

4.96 out of 5 average rating, 189 reviews

TreeTop at Mt Run Lake (Private Guest Apartment)

Spacious one bedroom guest apartment with SEPARATE ENTRANCE, private separate patio and reserved parking in this newly decorated full apartment, set on four acres with lakefront views situated in the foothills of the Blue Ridge Mountains. One flight of stairs up to a beautiful apartment with fantastic views of the lake and surrounding property. Private and secluded yet only 10 minutes from Historic downtown Culpeper with its many restaurants, local shops, grocery stores and pharmacies.

Top guest favorite

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, 195 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 favorite

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, 237 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 favorite

The spacious deck extends along the length of the house, featuring several white rocking chairs positioned for scenic views of the surrounding landscape. Cloudy skies create a serene atmosphere, highlighting the natural beauty of the nearby hills and fields.

Home in Madison

4.96 out of 5 average rating, 163 reviews

Spacious Shenandoah Home on 35 Private Acres

Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.

Top guest favorite

A private cottage is nestled under a large tree, surrounded by well-kept grassy areas. The home features large windows that enhance natural light, with a welcoming entrance leading to a small staircase. The peaceful rural landscape extends in the background.

Farm stay in Warrenton

4.98 out of 5 average rating, 656 reviews

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this independent private cottage on the homestead. Watch for deer, turkeys and birds in the field from the sunroom or take a hike around the farm. Centered in Fauquier's wine country it is ideal for the weekend escape, or day trips West to the mountains, East to DC or points south. Also, a perfect solution for accommodating family at get-to-gathers, wedding guest, or your "Halfway overnight stay" traveler North/ South or to the beach.

Top guest favorite

The exterior of a light blue cottage features a welcoming front porch with white railings. A red convertible sports car is parked on the gravel driveway. Lush greenery surrounds the property, complemented by a stone pathway leading to the entrance.

Home in Washington

5 out of 5 average rating, 159 reviews

Mint Cottage at Little Washington

Luxurious appointments, spacious living areas and breathtaking views await you at Mint Cottage at Little Washington! This 1400-square-foot home is just a 5-minute walk or a 1-minute drive to the world-renowned Inn at Little Washington, and a short drive to spectacular hiking in Shenandoah National Park, Three Blacksmiths, craft breweries, distilleries and wineries, shops and so much more. A modern, stylish, and comfortable place to retreat, relax and reinvigorate.

Top guest favorite

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

4.98 out of 5 average rating, 199 reviews

The Bunkhouse- 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 bunkhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.