Holiday houses in Roseland

4.96 out of 5 average rating, 701 reviews

Cabin in Roseland

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.

4.92 out of 5 average rating, 581 reviews

Guesthouse in Afton

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

4.92 out of 5 average rating, 583 reviews

Farm stay in Nellysford

The Cottage at Spindle Hill: an Artist’s Farm

Relax and unwind in this fabulous handcrafted cottage— every detail has been considered! Beautiful mountain setting on small, historical farm just off Blue Ridge Parkway, the heart of Virginia wine country. Deep, hand-built cedar hot-tub. Minutes to the Appalachian Trail and Wintergreen resort. An easy walk to public trails, Devil's Backbone Brewery and Bold Rock Cidery. Beautiful gardens, hammocks, featured in design blogs. High-speed fiber internet. Library. Hens. Miniature Goats. EV Charger.

4.99 out of 5 average rating, 160 reviews

Yurt in Roseland

Across from Devil’s Backbone~5mi to Lake & Hikes!

Come for a memorable stay at the Rockfish Valley Yurt and enjoy "glamping" at its finest! Picturesque mountain views await at this magical yurt conveniently located ON the “151 Brew Ridge Trail", on 3 acres close to popular attractions- Nat. Park & hiking 2 mi, Lake 10 mi, Devils Backbone Brewery 1 mi, Bold Rock 2 mi & Wintergreen Ski & Spa 10 mi. You’ll have 15+ wineries & breweries within a 20 min radius. It’s a one of a kind experience! Create memories here that will last a lifetime!

5 out of 5 average rating, 252 reviews

Cottage in Tyro

Bear Creek Inn

You will be renting the 2 bedroom cottage, optional 3rd bedroom, very large, fenced yard for your pet. Relax at this quiet, peaceful place with year round trout stream. Minutes from the breweries and wineries on Nelson 151. Plenty of outdoor activities to enjoy. The George Washington National Forest is across the street for exploring, hiking and hunting. The house is only 4 miles from Crabtree Falls and several minutes from the Appalachian Trail access. Wintergreen Resort is 12 miles away.

5 out of 5 average rating, 221 reviews

Cottage in Roseland

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!)!

4.9 out of 5 average rating, 124 reviews

Guest suite in Roseland

Dogwood Suite at Open Heart Inn

Welcome to your country retreat! This unique section of the farmhouse was originally built in 1840, and features a cozy, king-sized bed. Relax on your private front porch, enjoy the views from the back patio, explore our 10 acres of farmland, take in the dogwoods and beautiful flowers, and get away from it all! Minutes from the Appalachian Trail, Devil's Backbone, and much more-- we are perfectly located to explore the trails, breweries, and wineries of scenic Nelson County.

4.93 out of 5 average rating, 274 reviews

Guesthouse in Lowesville

Scenic Cabin+river+hot tub No cleaning/pet fees!

Relax in the river or hot tub at this cozy 180 sq ft. cabin on 7 acres. Build a fire by the river or grill on your private patio. The charmingly decorated area includes a small kitchen sink with a mini fridge, microwave, hot plate and coffeemaker as well as a small sitting area with TV in addition to the bedroom & bathroom. The patio has an umbrella, lounge chairs and bar stools for al fresco dining as well as a grill. Bring your pet for scenic walks through the fields.

Condo in Wintergreen Resort

4.98 out of 5 average rating, 236 reviews

Best View in the Blue Ridge from Biscuit's Porch

One of the best sunrise views in the Blue Ridge Mountains! Spend your days hiking over 30+ miles of trails (including the Appalachian Trail), driving the Blue Ridge Parkway, kayaking in the lake in the summer, skiing one of the regions best mountains in the winter, or exploring Virginia's brewery and wine country. Whichever you chose, we're certain you'll enjoy your time at Biscuit's Porch. We're excited to help you have the best Blue Ridge Getaway!

4.92 out of 5 average rating, 257 reviews

Tiny home in Roseland

The Humble Abode Camp

The Humble Abode is a secluded CAMP & offers a scenic view of DePriest Mountains range and is the perfect place to un-plug & disconnect to reconnect!! Our private and secluded camp provides with spectacular mountain views and a NEW OUTDOOR Shower!! with pressurized ambient water temperature, spacious deck, covered porch, double bed, hammock, yard to play croquet/corn hole, private port-a-potty, charcoal grill, and a solo stove firewood pit.

Superhost

4.89 out of 5 average rating, 111 reviews

Fleetwood (c. 1809) - A renovated landmark

Built in 1809 as a country home and renovated in 2019, Fleetwood is great balance of old-world charm and modern convenience located right in the middle of Nelson County's music, craft beer, and adventure destinations. Fleetwood sits atop a private bluff of solid rock overlooking the Tye River, with beautiful views of the Blue Ridge Mountains. When you visit you’ll feel that people have enjoyed this special spot for thousands of years.

4.97 out of 5 average rating, 448 reviews

Home in Amherst

The Vixen House

This cozy and comfortable home is located within the charming Town of Amherst in a quiet neighborhood very close to Sweet Briar College. It is only a short drive from Lynchburg yet is also convenient to other area attractions, such as the Blue Ridge Parkway, Appalachian Trail, Mt. Pleasant Scenic Area, Wintergreen Resort, and an assortment of local restaurants, wineries, and breweries, including the Rt. 151 "Brew Ridge Trail."

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Popular amenities for Roseland holiday rentals

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Other great holiday rentals in Roseland

Condo in Wintergreen Resort

4.83 out of 5 average rating, 58 reviews

Cozy 1-bedroom Condo with Fireplace Near Ski Slope

JimRating, 5 stars2 months ago

Laleh is a great and perfect host. I have stayed with her numerous times and I have enjoyed her space, her continued communication and her quickness to address any number of questions. Enjoy your stay with her.

Treehouse in Stanardsville

5 out of 5 average rating, 43 reviews

CloudPointe Retreat

KevinRating, 5 stars6 days ago

This place was awesome the views are incredible and the privacy was like nowhere else. As long as you have 4wd and don’t mind some steps this is a perfect place for couples. Everything was clean and exactly as described. Kevin was even proactive in letting us know the power had went out before we got there and then immediately let us know it was back on. This place really is a hidden gem and you are within 15-30 minutes of restaurants and shopping. We will definitely try to stay here again in the future.

Superhost

4.79 out of 5 average rating, 48 reviews

Cozy Country small two bedroom home.

StefanieRating, 5 stars2 weeks ago

My husband and two young kids stayed over the weekend. It was perfect. It was exactly as described. I loved how clean it was and how it had every thing you needed. The location was amazing. We played in creeks, fished, hiked, and stayed up late with family board games. My kids said they didn’t want to leave. Thank you so much for a wonderful stay!!!

Apartment in Wintergreen Resort

4.97 out of 5 average rating, 86 reviews

Mountain View Nest

BridgetRating, 5 stars1 week ago

We loved our stay at Becky’s place! The detailed check-in instructions made finding and getting into the unit a breeze. The views from the porch were absolutely gorgeous, and we appreciated all of the recommendations for hiking and vineyards. Overall, it was a fantastic experience!

4.94 out of 5 average rating, 54 reviews

Farmette! On River by Wintergreen & Blue Ridge Pkw

AmyRating, 5 stars5 months ago

We had a wonderful stay over New Years - convenient to Wintergreen and lots of cool spots to eat. We thoroughly enjoyed the property (the fresh eggs were a bonus) and hostess Amy was very responsive and nice. Thank you for allowing us to stay at such a cool little place - we made wonderful memories there together!

4.91 out of 5 average rating, 22 reviews

Cabin in Roseland

The Retreat at Persimmon Hill

EmilyRating, 5 stars1 month ago

Elizabeth was a great host and the Cabin was a wonderful place to stay! We would be happy to stay there again!

5 out of 5 average rating, 7 reviews

Guesthouse in Amherst

Sleepy Fox Cottage

LanceRating, 5 stars1 week ago

This was a great cottage to stay in for a weekend getaway with my partner. The space was cozy and had everything we needed: comfy bed, large TV, full size fridge, and kitchen supplies. We wound up buying groceries at food lion (one block away) so we only ate out once during our whole stay. Kitchen utensils included pots and a pan, dishes, a cooking hot plate with space for 2 pans, a coffeemaker, and a toaster. There is no microwave. I brought my own electric hot water kettle to make tea. All in all this was a comfy, great stay, accessible (no stairs), and there is even a Tesla ev charger for anyone that needs it. Highly recommend for 1-2 people for a nice weekend away.