Roseland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Roseland vacation rentals

Outdoor dining

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is ￥20,202
￥45,637 total
includes taxes & fees
May 17 - May 18
Historic Bungalow 30 minutes from Wintergreen
Smart TV, DVD player, books, music library

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (103 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is ￥20,435
￥30,893 total
includes taxes & fees
May 17 - May 18
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Terrace/patio

Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
Roseland
8.4 out of 10, Very Good, (9 reviews)
"This house is perfect for a girls weekend. We did a couple places further out but enjoyed Bold Rock and Devils Backbone. It had everything we needed to enjoy some much needed time to relax at the house also. "
United States
Katherine N.
The price is ￥18,077
￥45,898 total
includes taxes & fees
May 13 - May 14
Bluebird Cottage: Near 151 + Appalachian Trail
Beach towels

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (19 reviews)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is ￥21,221
￥38,837 total
includes taxes & fees
May 19 - May 20
Cozy Country small two bedroom home.
Property grounds

Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA

Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA
Roseland
10.0 out of 10, Exceptional, (32 reviews)
"This was another great stay at one of Lorraine's properties. It had everything we needed for our multi-family ski trip! Thanks again, we hope to be back soon!"
United States
Aaron Y.
The price is ￥36,154
￥55,782 total
includes taxes & fees
May 13 - May 14
Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA
Smart TV, fireplace

Bide-a-Wee- Hike the Trails! Close to the slopes!

Bide-a-Wee- Hike the Trails! Close to the slopes!
Wintergreen Resort
9.2 out of 10, Wonderful, (12 reviews)
"The host was great and very responsive. We have stayed here now twice. Since our last stay, the kitchen and upstairs bath have been nicely renovated (new counter tops and tile etc.) The home is nicely appointed with typically needed items. The floor was very dirty and the kitchen amenities need a review and refresh! The increase in price due to the new counters and tile isn't overcome by no other updates and not so clean property! Those are our only pieces of feedback and easily fixed. ...
United States
Lauren M.
The price is ￥17,109
￥50,104 total
includes taxes & fees
May 13 - May 14
Bide-a-Wee- Hike the Trails! Close to the slopes!
Smart TV, fireplace, DVD player, foosball

Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking

Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking
Roseland
9.8 out of 10, Exceptional, (24 reviews)
"Everything was great. Views were awesome and game room was a great hangout."
United States
Rob T.
The price is ￥63,348
￥78,863 total
includes taxes & fees
May 13 - May 14
Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking
Terrace/patio

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Chestnut Springs
10.0 out of 10, Exceptional, (17 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
The price is ￥29,434
￥77,009 total
includes taxes & fees
May 17 - May 18
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Sauna

Barrel Sauna, Hot Tub & Views

Barrel Sauna, Hot Tub & Views
Roseland
10.0 out of 10, Exceptional, (1 review)
"House was beautiful and well maintained."
United States
Collin W.
The price is ￥25,465
￥52,252 total
includes taxes & fees
Jun 1 - Jun 2
Barrel Sauna, Hot Tub & Views
Terrace/patio

Mountain Mindset: Pup Friendly + Trail

Mountain Mindset: Pup Friendly + Trail
Laurel Ridge
9.6 out of 10, Exceptional, (10 reviews)
"Gorgeous setting and incredibly cozy. Perfect for our holiday family gathering!"
United States
Calli S.
Mountain Mindset: Pup Friendly + Trail
Terrace/patio

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is ￥39,298
￥88,439 total
includes taxes & fees
May 19 - May 20
Mountain Retreat: Year-Round Getaway, Pup Friendly
Smart TV, fireplace, video games, DVD player

Pet Friendly with Mountain views ON 151 BrewRidge Trl near Wineries~Hikes~Skiing

Pet Friendly with Mountain views ON 151 BrewRidge Trl near Wineries~Hikes~Skiing
Roseland
10.0 out of 10, Exceptional, (5 reviews)
"Very well stocked cabin. Location was amazing. We enjoyed our stay so much!!"
United States
Peggy M.
The price is ￥28,153
￥71,335 total
includes taxes & fees
May 13 - May 14
Pet Friendly with Mountain views ON 151 BrewRidge Trl near Wineries~Hikes~Skiing
Exterior

Three Ridges 05 With Wintergreen Advantage

Three Ridges 05 With Wintergreen Advantage
Chestnut Springs
The price is ￥37,568
￥66,346 total
includes taxes & fees
May 13 - May 14
Three Ridges 05 With Wintergreen Advantage
Exterior

White Oak 51 with Wintergreen Advantage

White Oak 51 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Had a great thanksgiving with family. Wood burning fireplace with wood stacked just outside condo. Kitchen had all needed utensils. Having wintergreen advantage was a major plus—allowing access to gym and spa"
United States
Nathan S.
The price is ￥43,856
￥74,290 total
includes taxes & fees
May 13 - May 14
White Oak 51 with Wintergreen Advantage
Exterior

Above The Clouds with Wintergreen Advantage

Above The Clouds with Wintergreen Advantage
Wintergreen
The price is ￥45,428
￥94,944 total
includes taxes & fees
May 22 - May 23
Above The Clouds with Wintergreen Advantage
Exterior

Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!

Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!
Roseland
The price is ￥96,554
￥167,212 total
includes taxes & fees
May 16 - May 17
Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!
Exterior

Branch and Barrel: Hot Tub & Sauna + Mtn Views

Branch and Barrel: Hot Tub & Sauna + Mtn Views
Roseland
The price is ￥56,903
￥119,180 total
includes taxes & fees
May 26 - May 27
Branch and Barrel: Hot Tub & Sauna + Mtn Views
Standard Suite, 1 Queen Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (56 reviews)
"Great place to stay during our trip to Crozet. Very clean and spacious suites. Great location."
United States
Tatyana
The price is ￥12,378
￥13,777 total
includes taxes & fees
May 17 - May 18
Affordable Suites of America Waynesboro
Interior

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is ￥14,147
￥23,407 total
includes taxes & fees
May 17 - May 18
Whole House
Smart TV

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Buena Vista
9.8 out of 10, Exceptional, (28 reviews)
"Nice and cozy home for overnight stays "
United States
Yahima O.
The price is ￥15,719
￥29,742 total
includes taxes & fees
May 25 - May 26
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Roseland Hotel Reviews

Sleep Inn Staunton

Sleep Inn Staunton

10/10 Excellent
"Yes"
Linda 3-night trip
Posted 3 hours ago
Sleep Inn Staunton

Find out more about Roseland

Search for holiday rentals in Roseland on Expedia! You can easily find your home rentals, villas, holiday apartments in Roseland using one of the methods below:

  • View our selection of featured holiday rentals in Roseland
  • Use the map to find apartments and other holiday homes in the Roseland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Roseland while they last

Look no further and take a look at our great range of rental properties in Roseland!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Roseland?

Yes, we offer vacation rentals near the most popular attractions in Roseland, or you can go with a secluded option if you're looking for relaxation. Discover why Roseland is known for its ski slopes and mountain landscape. While you're here, grab a bite or have a drink at the breweries.

What are some of the best vacation home rentals in Roseland?

Alone Mill Schoolhouse - A paradise for outdoor lovers: This vacation home rental outside of Roseland is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Roseland?

Choose from 81 Expedia vacation rentals in Roseland for a memorable vacation.

What’s there to see and do in Roseland?

George Washington National Forest and Reids Gap Trailhead are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Wintergreen Resort and Woodson's Mill.

What’s a vacation rental in Roseland like?

Vacation rentals are private properties you can stay in for short or long periods in Roseland. Vacation rentals provide amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.