Roseland Holiday Rentals

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Check prices for these dates

Tonight
18 July - 19 July
Tomorrow
19 July - 20 July
This weekend
18 July - 20 July
Next weekend
25 July - 27 July

Holiday Rentals in Roseland

Historic Bungalow 30 minutes from Wintergreen
Exterior

Historic Bungalow 30 minutes from Wintergreen

10.0 out of 10, Exceptional, (10)
"I love this place. I’ve stayed there one previous time and it was just as wonderful. Peaceful beautiful home for a relaxing vacation."
The price is AU$380
includes taxes & fees
21 July - 22 July
Historic Bungalow 30 minutes from Wintergreen
Cozy Country small two bedroom home.
Smart TV, DVD player

Cozy Country small two bedroom home.

9.6 out of 10, Exceptional, (15)
"This was a nice cozy comfortable house nearby Crabtree falls hiking! We would stay here again."
The price is AU$373
includes taxes & fees
26 July - 27 July
Cozy Country small two bedroom home.
Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room
Terrace/patio

Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room

10.0 out of 10, Exceptional, (12)
"We enjoyed the space, amenities and location!"
The price is AU$690
includes taxes & fees
29 July - 30 July
Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room
Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking
Outdoor dining

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

10.0 out of 10, Exceptional, (16)
"Beautiful, clean and well stocked mountain property that has everything you need for a wonderful stay."
The price is AU$831
includes taxes & fees
20 July - 21 July
Spacious, private, four-season home built on mountainside with great proximity to Wintergreen, breweries, cideries, and hiking
Possum Trot Lodge - Wedding & Event Venue, Lodging for 18, Stone Fireplace
Property grounds

Possum Trot Lodge - Wedding & Event Venue, Lodging for 18, Stone Fireplace

10.0 out of 10, Exceptional, (1)
"The Lodge at Possum Trot is a truly relaxing, cozy country retreat. It is comfortably furnished, beautifully decorated and completely equipped. Judith is a very attentive host and actively ensured we had a great visit. If you enjoy a roaring fire, cooking together and being with your loved ones, this is your place."
The price is AU$1,233
includes taxes & fees
22 July - 23 July
Possum Trot Lodge - Wedding & Event Venue, Lodging for 18, Stone Fireplace
Possum Trot Farmhouse - Wedding & Event Venue, Lodging for 18, Stone Fireplace
Smart TV, fireplace, offices, printers

Possum Trot Farmhouse - Wedding & Event Venue, Lodging for 18, Stone Fireplace

10.0 out of 10, Exceptional, (10)
"Possum Trot is a slice of heaven on earth! Tucked away in the rolling hills, this property was great for a big group of 14 celebrating the New Year. Judith is a communicative and gracious host. Would absolutely stay again!"
The price is AU$2,295
includes taxes & fees
22 July - 23 July
Possum Trot Farmhouse - Wedding & Event Venue, Lodging for 18, Stone Fireplace
Wintergreen 5BR with Hot Tub, Sauna, Firepit
Terrace/patio

Wintergreen 5BR with Hot Tub, Sauna, Firepit

Wintergreen 5BR with Hot Tub, Sauna, Firepit
Branch and Barrel: Hot Tub & Sauna + Mtn Views
Exterior detail

Branch and Barrel: Hot Tub & Sauna + Mtn Views

The price is AU$1,077
includes taxes & fees
6 Aug - 7 Aug
Branch and Barrel: Hot Tub & Sauna + Mtn Views
Designer Home w/ Incredible Views, Sleeps 16
Terrace/patio

Designer Home w/ Incredible Views, Sleeps 16

9.6 out of 10, Exceptional, (8)
"perfect for family gathering layout of house, views, host very helpful"
The price is AU$2,190
includes taxes & fees
22 July - 23 July
Designer Home w/ Incredible Views, Sleeps 16
Wintergreen Luxury, Breathtaking Views
Outdoor dining

Wintergreen Luxury, Breathtaking Views

Wintergreen Luxury, Breathtaking Views
Charming 4bedroom single story home in Wintergreen VA. 2Primary suites, flat lot
Outdoor dining

Charming 4bedroom single story home in Wintergreen VA. 2Primary suites, flat lot

The price is AU$1,284
includes taxes & fees
31 July - 1 Aug
Charming 4bedroom single story home in Wintergreen VA. 2Primary suites, flat lot
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Outdoor dining

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

2.0 star property
The price is AU$452
includes taxes & fees
22 July - 23 July
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Waynesboro Home Near Wintergreen Charlottesville
House

Waynesboro Home Near Wintergreen Charlottesville

2.0 star property
The price is AU$892
includes taxes & fees
20 July - 21 July
Waynesboro Home Near Wintergreen Charlottesville
Charming Basement apartment! Great for Families.
Interior

Charming Basement apartment! Great for Families.

9.4 out of 10, Exceptional, (6)
"The owner was amazing"
The price is AU$215
includes taxes & fees
24 July - 25 July
Charming Basement apartment! Great for Families.
Updated, Cheerful Home Minutes to SVU, VMI and W&L
Property grounds

Updated, Cheerful Home Minutes to SVU, VMI and W&L

9.0 out of 10, Wonderful, (26)
"The property was easy to navigate to and the neighborhood was very quiet. It had a nice big yard and the theatre room was fun!"
The price is AU$334
includes taxes & fees
20 July - 21 July
Updated, Cheerful Home Minutes to SVU, VMI and W&L
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Outdoor dining

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

10.0 out of 10, Exceptional, (3)
"We had a brief stay but it had all the amenities we needed and was very clean and welcoming. Thank you."
The price is AU$468
includes taxes & fees
20 July - 21 July
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Interior

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

10.0 out of 10, Exceptional, (18)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
The price is AU$235
includes taxes & fees
28 July - 29 July
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Outdoor dining

Secluded 20+ Acre Retreat Near Brew & Wine Trails

9.8 out of 10, Exceptional, (7)
"The house was clean and very comfortable. Plenty of room for the dog to run around through the woods and for how secluded its only minutes from the distilleries and wineries"
Secluded 20+ Acre Retreat Near Brew & Wine Trails
The Firefly Springhouse
Exterior

The Firefly Springhouse

10.0 out of 10, Exceptional, (30)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is AU$178
includes taxes & fees
29 July - 30 July
The Firefly Springhouse
Pine Creek Tiny House
Outdoor dining

Pine Creek Tiny House

10.0 out of 10, Exceptional, (1)
"The place was clean, comfy and well stocked. We would love to return."
The price is AU$391
includes taxes & fees
20 July - 21 July
Pine Creek Tiny House
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

Hotel 24 South

Hotel 24 South

10/10 Excellent
"This is a lovely old hotel in the heart of the town. It was our second time staying here and we were pleased with both the beauty of the hotel and the friendly staff."
Barbara 1-night trip
Posted 1 day ago
Hotel 24 South

Frequently asked questions

Can I find holiday rentals in Roseland?

Yes, there are holiday rentals close to the most popular sights in Roseland, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Roseland has to offer?

Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking: This highly rated holiday home rental in Roseland is located in the mountains, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Other favourite homes for rent in Roseland are Insane Mountain Views - New Listing and Luxury 5Bd 4Ba Sleeps 16+ Hot-tub/Dog Friendly.

How many holiday rentals are there in Roseland?

Choose from 77 Expedia holiday rentals in Roseland for a memorable holiday.

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 holiday rental in Roseland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roseland. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips or small group gatherings.