Book Holiday Homes in Delaplane

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 Delaplane

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

Delaplane
Located in Delaplane, this vacation home is within a 5-minute drive of RdV Vineyards and Delaplane Cellars.
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Modern Home on Middleburg Equestrian Farm

Modern Home on Middleburg Equestrian Farm

Middleburg
Located in Middleburg, this vacation home is within a 15-minute drive of Glenwood Park and Red Fox Fine Art.
Modern Home on Middleburg Equestrian Farm
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

Front Royal
When you stay at this vacation home in Linden, you'll be in the mountains, within a 5-minute drive of George Richard Thompson State Wildlife Management Area ...
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Save an average of 15% on thousands of hotels when you're signed in
Gruner Bungalow at Otium Cellars

Gruner Bungalow at Otium Cellars

Purcellville
Located in Purcellville, this vacation home is in a rural location, a 3-minute drive from Franklin Park and 7 minutes from Fireman's Field.
Gruner Bungalow at Otium Cellars
Modern Country House on the Shenandoah River

Modern Country House on the Shenandoah River

Charles Town
When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.
Modern Country House on the Shenandoah River
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Leesburg
Located in Leesburg, this vacation home is in a rural location, within a 5-minute drive of Catoctin Valley and Oatlands Historic House and Gardens.
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Markham
With a stay at this vacation home, you'll be centrally located in Linden, within a 15-minute drive of Naked Mountain Winery & Vineyards and Aspen Dale Winery ...
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.

This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.

Winchester
Located in Winchester, this vacation home is in a rural location, a 4-minute drive from Appleland Sports Center and 6 minutes from The Kernstown ...
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
 Shenandoah mountain view home King bed StarLink EV port river access 90 min DC

Shenandoah mountain view home King bed StarLink EV port river access 90 min DC

Bentonville
Located in Bentonville, this vacation home is on a river, within a 15-minute drive of George Washington National Forest and Hazard Mill Recreation Area.
Shenandoah mountain view home King bed StarLink EV port river access 90 min DC
Don't see what you're looking for?
See all available properties in Delaplane
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.

Delaplane 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 Delaplane vacation homes are the perfect way for you to wing it.

Holiday houses in Delaplane 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 Delaplane 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 Delaplane adventures, obvs.

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

Delaplane Holiday Homes essential information

Accommodation
158 Holiday Homes
Lowest Price
AU$161
Highest Price
AU$1,119
Popular accommodation
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine, Modern Home on Middleburg Equestrian Farm, #CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries, Gruner Bungalow at Otium Cellars, Modern Country House on the Shenandoah River , Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia, Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains , This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA., Shenandoah mountain view home King bed StarLink EV port river access 90 min DC

Top trending hotels in Delaplane

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

Delaplane
Located in Delaplane, this vacation home is within a 5-minute drive of RdV Vineyards and Delaplane Cellars.
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Delaplane
Located in Delaplane, this vacation home is in a rural location, within a 15-minute walk of Barrel Oak Winery and Blue Valley Vineyard And Winery.
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 6 Apr to 7 Apr
AU$161
includes taxes & fees
6 Apr - 7 Apr
With a stay at La Quinta Inn & Suites by Wyndham Winchester in Winchester, you'll be in the business district, just a 3-minute walk from Shenandoah University ...
La Quinta Inn & Suites by Wyndham Winchester
Save an average of 15% on thousands of hotels when you're signed in
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$1,119 per night from 1 Apr to 2 Apr
AU$1,119
includes taxes & fees
1 Apr - 2 Apr
Located in Middleburg, Salamander Resort And Spa is in the historical district, within a 15-minute drive of Greenhill Winery & Vineyards and Chrysalis ...
Salamander Resort And Spa
Don't see what you're looking for?
See all available properties in Delaplane
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.