A gravel road curving through a green field with a wooden fence on one side and mountains in the background.

Holiday Homes in Roseland

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Roseland holiday homes

A wooden deck with a blue planter table holding a yellow flower pot.

1. Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
9.8 out of 10, Exceptional, (19 reviews)
"Great location quiet area"
United States
Scott P.
The price is AU$409
includes taxes & fees
6 Nov - 7 Nov
Historic Bungalow 30 minutes from Wintergreen
A sauna with wooden benches and a view of a forested hillside.

2. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is AU$473
includes taxes & fees
28 Oct - 29 Oct
Branch and Barrel
A sandy beach with a lake and forested hills in the background.

3. 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 AU$393
includes taxes & fees
28 Oct - 29 Oct
Cozy Country small two bedroom home.
A two-story house with a covered porch, a stone pathway, and a well-maintained garden.

4. Blue Ridge Getaway

Blue Ridge Getaway
Roseland
The price is AU$1,038
includes taxes & fees
26 Oct - 27 Oct
Blue Ridge Getaway
A hallway with a wooden-framed mirror, a console table with a vase and a sculpture, a door with a glass panel, and a small rug on the floor.

5. Spacious, private, four-season mountainside home close to Wintergreen and hiking

Spacious, private, four-season mountainside home close to Wintergreen and hiking
Roseland
9.8 out of 10, Exceptional, (29 reviews)
"Very nice property. Quiet. Owners were very responsive and eager to assist although we didn't need anything during our stay."
United States
judson a.
The price is AU$762
includes taxes & fees
26 Oct - 27 Oct
Spacious, private, four-season mountainside home close to Wintergreen and hiking
A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

6. Adventure Awaits

Adventure Awaits
Laurel Ridge
9.0 out of 10, Wonderful, (10 reviews)
"our stay was so fun! "
United States
Kaden C.
The price is AU$829
includes taxes & fees
3 Nov - 4 Nov
Adventure Awaits
A deck with a fire pit, outdoor furniture, and a view of trees and a sunset.

7. Wintergreen cabin, 5 min to ski, hot tub, sauna

Wintergreen cabin, 5 min to ski, hot tub, sauna
Chestnut Springs
10.0 out of 10, Exceptional, (16 reviews)
"Family friendly in every way possible! My friends and I had the best experience with the nearby hikes, overlooks, and overall destination of the home! Awesome place to stay!"
United States
mikenzi b.
The price is AU$738
includes taxes & fees
20 Oct - 21 Oct
Wintergreen cabin, 5 min to ski, hot tub, sauna
A cabin with a deck, outdoor seating, and a fire pit.

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

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Chestnut Springs
9.8 out of 10, Exceptional, (20 reviews)
"Great stay!"
United States
Cheryl P.
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A stone fireplace with seating, surrounded by a gravel area and overlooking a forested hillside.

9. Barrel Sauna, Hot Tub & Views

Barrel Sauna, Hot Tub & Views
Roseland
10.0 out of 10, Exceptional, (2 reviews)
"House was beautiful and well maintained."
United States
Collin W.
The price is AU$556
includes taxes & fees
17 Nov - 18 Nov
Barrel Sauna, Hot Tub & Views
A large white house with a green roof, a patio with outdoor furniture, and a swimming pool.

10. Branch and Barrel: Hot Tub & Sauna + Mtn Views

Branch and Barrel: Hot Tub & Sauna + Mtn Views
Roseland
The price is AU$1,195
includes taxes & fees
17 Nov - 18 Nov
Branch and Barrel: Hot Tub & Sauna + Mtn Views
A two-story house with a deck, outdoor furniture, and a covered patio area.

11. On Mountain Time: 5BR, 3 mins to Devil's Backbone

On Mountain Time: 5BR, 3 mins to Devil's Backbone
Roseland
The price is AU$1,197
includes taxes & fees
17 Nov - 18 Nov
On Mountain Time: 5BR, 3 mins to Devil's Backbone
A bedroom with a bed, a bedside table, a window, and a view of trees.

12. On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is AU$1,097
includes taxes & fees
20 Oct - 21 Oct
On Mountain Time
A wooden deck with outdoor furniture, including chairs and tables, surrounded by trees.

13. Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is AU$1,014
includes taxes & fees
17 Nov - 18 Nov
Mountain Retreat: Year-Round Getaway, Pup Friendly
A wooden deck with outdoor seating and a fire pit.

14. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AU$909
includes taxes & fees
17 Nov - 18 Nov
Mountain Mindset
A kitchenette with a coffee machine, mugs, and a sign on the wall.

15. Whole House

Whole House
Amherst
9.6 out of 10, Exceptional, (44 reviews)
"Nice place overall, we enjoyed our stay. It was right down the road from our family. It was super convenient and just what we needed for the weekend."
United States
Pam B.
The price is AU$212
includes taxes & fees
20 Oct - 21 Oct
Whole House
A modern kitchen with a central island, stainless steel appliances, and wooden cabinetry.

16. Peaceful stay at the Colleen cottage!

Peaceful stay at the Colleen cottage!
Arrington
10.0 out of 10, Exceptional, (6 reviews)
"Peaceful, beautiful, and a convenient location. I highly recommend this spacious clean home on beautiful land."
United States
Pam H.
The price is AU$483
includes taxes & fees
28 Oct - 29 Oct
Peaceful stay at the Colleen cottage!
A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

17. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is AU$434
includes taxes & fees
20 Oct - 21 Oct
Tucked Inn: Lower Unit
A swimming pool with a stone border, surrounded by lounge chairs and a wooden deck.

18. Farmhouse getaway for family vacations and friend retreats - heated pool

Farmhouse getaway for family vacations and friend retreats - heated pool
Roseland
10.0 out of 10, Exceptional, (41 reviews)
"The house was the perfect getaway for our family trip! There was plenty of room for all the kids and adults. Very well equipped for all your needs (towels, kitchen items, linens). Kids were occupied the whole time between the pool, playhouse, barn arcade, and outdoor space to run around. We will be back again!"
United States
Libera G.
The price is AU$712
includes taxes & fees
20 Oct - 21 Oct
Farmhouse getaway for family vacations and friend retreats - heated pool
A modern kitchen with green cabinets, stainless steel appliances, and a dining area with a blue wall and a poster.

19. Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Nellysford
9.8 out of 10, Exceptional, (9 reviews)
"Adorable, clean and quiet stay! The place was nicer than expected. It's obvious the hosts are thoughtful of their guests - we found everything we needed and more. A short drive into Nellysford and tucked away in the trees. "
United States
Katie K.
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
A sandy beach with a lake and forested hills in the background.

20. House / hot tub/pet friendly

House / hot tub/pet friendly
Tyro
9.8 out of 10, Exceptional, (76 reviews)
"Very easy check in. We really enjoyed our stay!!"
United States
Mike B.
The price is AU$600
includes taxes & fees
21 Oct - 22 Oct
House / hot tub/pet friendly
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.
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Top Roseland Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

8/10 Good
"The room was clean and the staff were very accommodating"
diane 2-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Waynesboro East by IHG

Find out more about Roseland

Roseland Holiday Homes information

Number of reviews
291
Accommodation
566 Holiday Homes
Lowest Price
AU$212
Highest Price
AU$1,197