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

Holiday Homes in Roseland

  • 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
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Roseland holiday homes

Exterior

Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is €178
includes taxes & fees
12 Aug - 13 Aug
Branch and Barrel
Outdoor dining

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (17 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is €269
includes taxes & fees
19 Jul - 20 Jul
Historic Bungalow 30 minutes from Wintergreen
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 €223
includes taxes & fees
21 Jul - 22 Jul
Cozy Country small two bedroom home.
Pool

Relaxing Wintergreen Chalet

Relaxing Wintergreen Chalet
Chestnut Springs
8.0 out of 10, Very good, (21 reviews)
"Enjoyed our stay and the owner was very helpful and informative."
United States
richard r.
The price is €405
includes taxes & fees
15 Aug - 16 Aug
Relaxing Wintergreen Chalet
Exterior

On Mountain Time: NEW house near Devil's Backbone

On Mountain Time: NEW house near Devil's Backbone
Roseland
The price is €658
includes taxes & fees
17 Aug - 18 Aug
On Mountain Time: NEW house near Devil's Backbone
Sauna

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 €315
includes taxes & fees
12 Aug - 13 Aug
Barrel Sauna, Hot Tub & Views
Sauna

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
Terrace/patio

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
Mountain Retreat: Year-Round Getaway, Pup Friendly
Exterior

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is €488
includes taxes & fees
20 Jul - 21 Jul
Mountain Mindset
House, Private Bathroom (On Mountain Time) | Interior

On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is €613
includes taxes & fees
19 Jul - 20 Jul
On Mountain Time
House, Private Bathroom (Forever Farm) | Exterior

Forever Farm

Forever Farm
2.5 star property
Schuyler
The price is €341
includes taxes & fees
21 Jul - 22 Jul
Forever Farm
Exterior

Ideal for large family summery vacations or a few couples / girlfriends to spend a long wine weekend / mountain getaway

Ideal for large family summery vacations or a few couples / girlfriends to spend a long wine weekend / mountain getaway
Lovingston
10.0 out of 10, Exceptional, (43 reviews)
"This was a very nice stay. We weren't there long enough to enjoy the pool or hot tub. The host was very communicative and let us do a late checkout. Excellent spot for a family gathering. "
United States
Diane H.
The price is €775
includes taxes & fees
18 Aug - 19 Aug
Ideal for large family summery vacations or a few couples / girlfriends to spend a long wine weekend / mountain getaway
Interior

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (39 reviews)
"House was perfect for overnight stay. 30 min from Vines Center and easy to find."
United States
Unspecified U.
The price is €134
includes taxes & fees
20 Jul - 21 Jul
Whole House
Coffee/tea maker, fridge, microwave, oven

Peaceful stay at the Colleen cottage!

Peaceful stay at the Colleen cottage!
Arrington
10.0 out of 10, Exceptional, (2 reviews)
"Peaceful, beautiful, and a convenient location. I highly recommend this spacious clean home on beautiful land."
United States
Pam H.
The price is €324
includes taxes & fees
2 Aug - 3 Aug
Peaceful stay at the Colleen cottage!
Beach towels

House / hot tub/pet friendly

House / hot tub/pet friendly
Tyro
9.8 out of 10, Exceptional, (74 reviews)
"Very easy check in. We really enjoyed our stay!!"
United States
Mike B.
The price is €279
includes taxes & fees
17 Aug - 18 Aug
House / hot tub/pet friendly
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (68 reviews)
"Such a great little place! Quick drive to town, but far enough for a quiet night. Room had everything we needed (and then some) for a short stay, and all the animals were the sweetest added bonus. Would absolutely stay here again if we’re ever back in the area."
United States
Rebekah
The price is €104
includes taxes & fees
19 Jul - 20 Jul
The Firefly Springhouse
Smart TV, fireplace, books

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 €332
includes taxes & fees
20 Jul - 21 Jul
Spacious + Serene Mtn Top Escape, 4 En Suites
Interior

Hot Tub | Fire Pit | River | State Park | King Bed

Hot Tub | Fire Pit | River | State Park | King Bed
Wingina
9.6 out of 10, Exceptional, (13 reviews)
"The house was cozy, comfortable and clean. It's secluded nature setting was a perfect getaway. The hot-tub was a great treat as much as the sound of the stream and view. "
United States
Melissa C.
The price is €367
includes taxes & fees
1 Aug - 2 Aug
Hot Tub | Fire Pit | River | State Park | King Bed
Property grounds

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, (46 reviews)
"Great stay. Nice property in a very quiet neighborhood. "
United States
Kurtis W.
The price is €181
includes taxes & fees
21 Jul - 22 Jul
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Exterior

Family Time in Love, Virginia: Mountain Cabin Getaway

Family Time in Love, Virginia: Mountain Cabin Getaway
Love
The price is €511
includes taxes & fees
28 Jul - 29 Jul
Family Time in Love, Virginia: Mountain Cabin Getaway
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

The Gin Hotel, an Ascend Collection Hotel

The Gin Hotel, an Ascend Collection Hotel

10/10 Excellent
"great dinner on site. no need to leave."
edmund 1-night trip
Posted 4 hours ago
The Gin Hotel, an Ascend Collection Hotel

Find out more about Roseland

Roseland Holiday Homes information

Number of reviews
Accommodation
491 Holiday Homes
Lowest Price
€144
Highest Price
€784