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

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Roseland holiday homes

Exterior

1. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is £207
includes taxes & fees
31 Aug - 1 Sept
Branch and Barrel
Outdoor dining

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.
The price is £218
includes taxes & fees
10 Sept - 11 Sept
Historic Bungalow 30 minutes from Wintergreen
Beach

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 £186
includes taxes & fees
1 Sept - 2 Sept
Cozy Country small two bedroom home.
Living area

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 £358
includes taxes & fees
31 Aug - 1 Sept
Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking
Terrace/patio

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.
The price is £375
includes taxes & fees
31 Aug - 1 Sept
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Exterior

6. 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 £240
includes taxes & fees
31 Aug - 1 Sept
Barrel Sauna, Hot Tub & Views
Exterior

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

Branch and Barrel: Hot Tub & Sauna + Mtn Views
Roseland
The price is £545
includes taxes & fees
31 Aug - 1 Sept
Branch and Barrel: Hot Tub & Sauna + Mtn Views
Room

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

On Mountain Time: 5BR, 3 mins to Devil's Backbone
Roseland
The price is £586
includes taxes & fees
30 Aug - 31 Aug
On Mountain Time: 5BR, 3 mins to Devil's Backbone
Private kitchen

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

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is £428
includes taxes & fees
31 Aug - 1 Sept
Mountain Retreat: Year-Round Getaway, Pup Friendly
House, Private Bathroom (On Mountain Time) | Exterior

10. On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is £518
includes taxes & fees
30 Aug - 31 Aug
On Mountain Time
Exterior

11. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is £385
includes taxes & fees
31 Aug - 1 Sept
Mountain Mindset
Interior

12. 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 £113
includes taxes & fees
30 Aug - 31 Aug
Whole House
House, Private Bathroom (Tucked Inn: Lower Unit) | Exterior

13. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is £207
includes taxes & fees
31 Aug - 1 Sept
Tucked Inn: Lower Unit
Pool

14. 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.
The price is £399
includes taxes & fees
1 Sept - 2 Sept
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
Exterior

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, (47 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 £319
includes taxes & fees
31 Aug - 1 Sept
Ideal for family summer vacations or a few couples wine weekend/mountain getaway
Exterior

16. 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.
The price is £267
includes taxes & fees
31 Aug - 1 Sept
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Living area

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 £270
includes taxes & fees
30 Aug - 31 Aug
Spacious + Serene Mtn Top Escape, 4 En Suites
Outdoor dining

18. Secluded 20+ Acre Retreat Near Brew & Wine Trails

Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton
9.8 out of 10, Exceptional, (25 reviews)
"Very beautiful spot they have here. We enjoyed our stay here from chilling by the fire looking at the stars to a family breakfast in the spacious kitchen and dinning room. Only hiccup we find were some ant friends but that’s to be expected in the middle of the woods, so be aware of where you keep your food and to clean up after yourself. We’ll definitely be back. "
United States
Xavier V.
The price is £244
includes taxes & fees
30 Aug - 31 Aug
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Beach

19. 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 £245
includes taxes & fees
10 Sept - 11 Sept
House / hot tub/pet friendly
Property grounds

20. Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Buena Vista
9.0 out of 10, Wonderful, (47 reviews)
"Nice place to stay"
United States
Ann E.
The price is £152
includes taxes & fees
30 Aug - 31 Aug
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
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

avid hotel Staunton by IHG

avid hotel Staunton by IHG

10/10 Excellent
"100"
Peter 1-night trip
Posted 1 day ago
avid hotel Staunton by IHG

Find out more about Roseland

Roseland Holiday Homes information

Number of reviews
433
Accommodation
534 Holiday Homes
Lowest Price
£113
Highest Price
£586