Holiday houses in Roseland

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Top-rated holiday rentals in Roseland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.
Holiday home in Lovingston
4.97 out of 5 average rating, 263 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

Top Guest favourite
A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.
Cottage in Afton
5 out of 5 average rating, 247 reviews

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Top Guest favourite
The gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.
Cabin in Roseland
4.96 out of 5 average rating, 762 reviews

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

Top Guest favourite
An outdoor seating area features several Adirondack chairs arranged on a stone patio overlooking a wooded landscape, with bare trees extending toward the mountains in the distance. The communal game room includes a foosball table and a television mounted on a stone wall.
Cabin in Roseland
4.97 out of 5 average rating, 253 reviews

Blue Ridge Cabin~Mtn View~Gameroom~SNP & Lake 5mi

The Blue Ridge Cabin is at the base of the mountain on the “151 Brewridge Trail”, just mins to wineries, breweries, hiking, skiing, golfing & lake fun. Experience a mountain vaca in this fun bear-themed cabin on 2 private acres, tucked away yet close to it all! Enjoy 12+ wineries & breweries within 15mins, 1/2 mi to Devils Backbone Brewery, 1 mi to Bold Rock Cider, 10 mins to Appalachian Trail, Shenandoah Nat. Park & Wintergreen Ski Resort! Charlottesville/Waynesboro 30mins. A perfect home base!

Top Guest favourite
The unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.
Home in Afton
4.99 out of 5 average rating, 104 reviews

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Top Guest favourite
Home in Roseland
4.98 out of 5 average rating, 125 reviews

Stargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill

Relax with the family on 12 private acres at our peaceful, brand new construction farmhouse. We're just 12 miles to Wintergreen Ski Resort and Stoney Creek Golf, breweries, and wineries. Sleeps 8: K, K, Q + daybed w/ trundle. ★Amazing mountain views ★Hot tub for 6 people ★Outdoor shower ★Rockers, Adirondacks chairs for idle stargazing ★Gas grill ★Teak dining table seats 6 ★Indoor/outdoor gas fireplaces ★View 55” TV from comfy leather sofa/kitchen ★Pack 'n Play/Bassinet/High chair ★Mud room

Guest favourite
The image showcases a cozy front porch featuring two rocking chairs, perfect for enjoying mountain views. The living area displays a comfortable couch and a stylish coffee table. A private hot tub is visible on the rear deck, complemented by scenic outdoor seating arrangements.
Cottage in Afton
4.97 out of 5 average rating, 182 reviews

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Welcome to Towler Cottage, a getaway in the heart of Route 151 in Afton. The cottage is within minutes from the best wineries and breweries, great local trails, and the Blue Ridge Parkway! Relax in the hot tub on the rear deck, or sit out by the fire pit and gaze at the stars. Enjoy great mountain views from the front porch rocking chairs. With one bedroom with a queen bed, plus a pull-out couch in the living room, the cottage is perfect for couples. Located 25 minutes from Charlottesville.

Top Guest favourite
A quaint cottage is framed by a white picket fence, with a welcoming blue front door and vibrant flowers lining the walkway. Scenic mountains rise in the background, while lush trees and blooming dogwood add to the charming exterior.
Cottage in Roseland
5 out of 5 average rating, 249 reviews

Blue Ridge Cottage - 3 Miles to Wintergreen

Our little piece of Blue Ridge Heaven is ready to share! Cozy - 2 bedrooms (one king, one queen), 1 bath, 956 square feet - well appointed in a terrific location! Beautiful mountain view from the 360 square foot, partially covered deck; fiber optic TV and wi-fi; South Fork of the Rockfish River out back. 3 miles from Wintergreen Resort, 1 mile from Devil's Backbone; Close to great hiking/biking, and many wineries, breweries, cideries, and distilleries (if you're into that kind of thing!)!

Top Guest favourite
A cozy cabin is nestled among trees, featuring a metal roof and a spacious front porch with black rocking chairs. The gravel driveway leads to the entrance, surrounded by neatly trimmed bushes and a lush landscape.
Cabin in Lovingston
5 out of 5 average rating, 113 reviews

Cabin Overlooking Vineyards of Lovingston Winery

Step off your spacious front porch to stroll through the vineyards of Lovingston Winery! Bring your friends and spend the weekend in a cozy cabin with modern amenities in the famous Monticello wine region. This 64 acre property includes pre-civil war oak trees, mountain views, and a pond with otters! We encourage you to explore the property and enjoy a glass of Lovingston Wine. There's a chance you could be greeted by a mini horse or two! Sleeps 6 comfortably, cot for 7, extra charge.

Top Guest favourite
Home in Tyro
4.99 out of 5 average rating, 301 reviews

Creekside Retreat | Fire Pit + Big Fenced Yard

Wake up to the sound of the creek and end your evenings around the fire-pit in your fully private, fenced yard. Bear Creek is a peaceful, private Blue Ridge retreat designed for couples, families, and pet-friendly getaways. Inside enjoy three comfortable bedrooms, an open living space, and direct access to a gently babbling creek just steps from the backyard. Minutes to Crabtree Falls, the Appalachian Trail, and Nelson County wineries--yet tucked away in a quiet, relaxing setting.

Top Guest favourite
The front exterior of the house is shown, featuring a warm brick facade and a sloping lawn. A welcoming front porch is visible, adorned with a seasonal wreath. Large windows allow for natural light, and a pathway leads to the entrance.
Home in Lovingston
5 out of 5 average rating, 215 reviews

Ms Maria's Place - make yourself at home, relax!

Newly renovated house on a quiet cove road .2 miles off of Rte 29 between Charlottesville and Lynchburg. The property includes high speed 100 Mbps Internet, a 65" Smart TV, gas grill, and a fire pit with outdoor seating. Enjoy visiting the local restaurants, orchards, wineries, and breweries. You will be a short drive from hiking Crabtree Falls, the Blue Ridge Parkway, Humpback Rock, Wintergreen, and James River State Park. The Lovingston Winery is just minutes down the road!

Top Guest favourite
Cabin in Vesuvius
4.99 out of 5 average rating, 373 reviews

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Popular amenities for Roseland holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Nelson County
  5. Roseland