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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Roseland holiday homes

A sauna with wooden benches and a view of a forested hillside.

1. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is €242
includes taxes & fees
21 Sept - 22 Sept
Branch and Barrel
A wooden deck with a blue planter table holding a yellow flower pot.

2. Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (17 reviews)
"Great location quiet area"
United States
Scott P.
Historic Bungalow 30 minutes from Wintergreen
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 €220
includes taxes & fees
16 Sept - 17 Sept
Cozy Country small two bedroom home.
A spacious living room with a large sectional sofa, a dining area, and a kitchen. There is a staircase leading to an upper level.

4. 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, (29 reviews)
"Overall, just love this house."
United States
Matt B.
The price is €427
includes taxes & fees
3 Sept - 4 Sept
Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking
A cabin with a deck, outdoor seating, and a fire pit.

5. 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, (18 reviews)
"Great stay!"
United States
Cheryl P.
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A spacious living room with large windows, a wooden ceiling, and a chandelier.

6. Designer Home w/ Incredible Views, Sleeps 16

Designer Home w/ Incredible Views, Sleeps 16
Wintergreen Resort
9.4 out of 10, Exceptional, (23 reviews)
"We enjoyed our stay at this beautiful place. love to come back "
United States
Neda A.
The price is €968
includes taxes & fees
27 Sept - 28 Sept
Designer Home w/ Incredible Views, Sleeps 16
A large white house with a green roof, a patio with outdoor furniture, and a stone fireplace.

7. 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.
Barrel Sauna, Hot Tub & Views
A large white house with a green roof, a patio with outdoor furniture, and a swimming pool.

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

Branch and Barrel: Hot Tub & Sauna + Mtn Views
Roseland
Branch and Barrel: Hot Tub & Sauna + Mtn Views

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

On Mountain Time: 5BR, 3 mins to Devil's Backbone
Roseland
The price is €687
includes taxes & fees
3 Sept - 4 Sept
On Mountain Time: 5BR, 3 mins to Devil's Backbone

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

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
Mountain Retreat: Year-Round Getaway, Pup Friendly
A wooden front door with a glass panel and a doormat, a porch with a railing, and potted plants.

11. On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is €603
includes taxes & fees
14 Sept - 15 Sept
On Mountain Time
A wooden deck with outdoor seating and a fire pit.

12. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is €479
includes taxes & fees
9 Sept - 10 Sept
Mountain Mindset
A kitchenette with a coffee machine, mugs, and a sign on the wall.

13. Whole House

Whole House
Amherst
9.6 out of 10, Exceptional, (43 reviews)
"House was perfect for overnight stay. 30 min from Vines Center and easy to find."
United States
Unspecified U.
The price is €132
includes taxes & fees
15 Sept - 16 Sept
Whole House
A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

14. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is €242
includes taxes & fees
3 Sept - 4 Sept
Tucked Inn: Lower Unit
A grassy outdoor area with several blue Adirondack chairs and a swing set.

15. Ideal for family summer vacations or a few couples wine weekend/mountain getaway

Ideal for family summer vacations or a few couples wine weekend/mountain getaway
Lovingston
10.0 out of 10, Exceptional, (48 reviews)
"We loved our stay. Plenty of space, gorgeous view, pool, hot tub, and game room were a hit with the kids. We would love to stay again!"
United States
Katie W.
The price is €477
includes taxes & fees
3 Sept - 4 Sept
Ideal for family summer vacations or a few couples wine weekend/mountain getaway
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a stone deck.

16. Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries

Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
Roseland
10.0 out of 10, Exceptional, (41 reviews)
"Beautiful property. Everyone enjoyed the pool and was able to unwind. Easy check in and check out. Hope to be back."
United States
Ashley B.
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

17. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"Great place"
United States
Stephen M.
The price is €314
includes taxes & fees
3 Sept - 4 Sept
Spacious + Serene Mtn Top Escape, 4 En Suites
A cabin with a large window, surrounded by trees.

18. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A spacious living room with a stone fireplace, a wooden ceiling, and large windows offering a view of trees.

19. 4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.6 out of 10, Exceptional, (35 reviews)
"it is really excellent."
United States
RK D.
The price is €572
includes taxes & fees
21 Sept - 22 Sept
4 BR cabin mins to trails & breweries pets welcome
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, (75 reviews)
"Very easy check in. We really enjoyed our stay!!"
United States
Mike B.
The price is €288
includes taxes & fees
8 Sept - 9 Sept
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

Spark by Hilton Staunton

Spark by Hilton Staunton

10/10 Excellent
"The customer service rep at the desk. 100% helpful for getting the room we needed at the next Spark Hotel. 10 out of 10."
Ed 1-night trip
Posted less than an hour ago
Spark by Hilton Staunton

Find out more about Roseland

Roseland Holiday Homes information

Number of reviews
3
Accommodation
536 Holiday Homes
Lowest Price
€173
Highest Price
€705