Book Holiday Homes in Roseland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Roseland

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Charlottesville
Book a stay at this family-friendly vacation home in Charlottesville. Enjoy free WiFi, a garden, and patios. Popular attractions Ragged Branch Distillery and ...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Fairfield
Book a stay at this family-friendly vacation home in Fairfield. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Brownsburg Historic ...
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Alone Mill Schoolhouse - A paradise for outdoor lovers

Alone Mill Schoolhouse - A paradise for outdoor lovers

Lexington
Book a stay at this family-friendly vacation home in Lexington. Enjoy free WiFi, a garden, and a pool table. Popular attractions Lexington Valley Vineyard and ...
Alone Mill Schoolhouse - A paradise for outdoor lovers
Save an average of 15% on thousands of hotels when you're signed in
 Wintergreen Resort Post & Beam Home Beauty

Wintergreen Resort Post & Beam Home Beauty

Wintergreen Resort
Stay at this vacation home in Roseland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wintergreen Resort and Reids Gap Trailhead are ...
Wintergreen Resort Post & Beam Home Beauty
Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L

Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L

Lexington
The price is NZ$864 per night from 13 Apr to 14 Apr
NZ$864
includes taxes & fees
13 Apr - 14 Apr
Stay at this vacation home in Lexington. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Stonewall Jackson House and Stonewall Jackson ...
Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L
The Landmark: Luxury In Downtown Staunton

The Landmark: Luxury In Downtown Staunton

Staunton
Stay at this vacation home in Staunton. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions American Shakespeare Center and The Woodrow ...
The Landmark: Luxury In Downtown Staunton
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
The price is NZ$740 per night from 13 Apr to 14 Apr
NZ$740
includes taxes & fees
13 Apr - 14 Apr
Stay at this vacation home in Nellysford. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Private 3 bedroom, 2.5 bath home on 2 acres overlooking the Blue Ridge Mountains

Private 3 bedroom, 2.5 bath home on 2 acres overlooking the Blue Ridge Mountains

Glasgow
Stay at this vacation home in Glasgow. Enjoy free WiFi, a garden, and patios. Popular attractions Virginia Safari Park and Layne's Country Store are located ...
Private 3 bedroom, 2.5 bath home on 2 acres overlooking the Blue Ridge Mountains
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

Wintergreen Resort
Book a stay at this family-friendly vacation home in Roseland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wintergreen Resort and ...
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
Don't see what you're looking for?
See all available properties in Roseland
View all properties
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.

Roseland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Roseland vacation homes are the perfect way for you to wing it.

Holiday houses in Roseland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Roseland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Roseland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Roseland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Roseland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Roseland Holiday Homes essential information

Accommodation
490 Holiday Homes
Lowest Price
NZ$122
Highest Price
NZ$864
Popular accommodation
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious, Bud's Place, Southern Charm in the Shenandoah Valley of Virginia, Alone Mill Schoolhouse - A paradise for outdoor lovers, Wintergreen Resort Post & Beam Home Beauty, Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L, The Landmark: Luxury In Downtown Staunton, Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House., Private 3 bedroom, 2.5 bath home on 2 acres overlooking the Blue Ridge Mountains, NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

Top trending hotels in Roseland

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Roseland
The price is NZ$344 per night from 7 Apr to 8 Apr
NZ$344
includes taxes & fees
7 Apr - 8 Apr
Stay at this cabin in Roseland. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery ...
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

Roseland
Book a stay at this family-friendly cottage in Roseland. Enjoy free WiFi, a garden, and a pool table. Popular attractions Crabtree Falls and Woodson's Mill are ...
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Roseland
Book a stay at this family-friendly cottage in Roseland. Enjoy free WiFi, a garden, and patios. Popular attractions Crabtree Falls and Woodson's Mill are located ...
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Save an average of 15% on thousands of hotels when you're signed in
Wingate by Wyndham Waynesboro

Wingate by Wyndham Waynesboro

2.5 out of 5
20 Windigrove Dr, Waynesboro, VA
Fully refundableReserve now, pay when you stay
The price is NZ$122 per night from 27 Apr to 28 Apr
NZ$122
includes taxes & fees
27 Apr - 28 Apr
Book a stay at this business-friendly hotel in Waynesboro. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful ...
Wingate by Wyndham Waynesboro
Don't see what you're looking for?
See all available properties in Roseland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.