Book Holiday Homes in Dickerson

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Featured Holiday Homes in Dickerson

Breathtaking views  with an  indoor private pool, come escape with us

Breathtaking views with an indoor private pool, come escape with us

Bluemont
Located in Bluemont, this vacation home is in the mountains, a 3-minute drive from Twin Oaks Tavern Winery and 6 minutes from Hill High Country Store.
Breathtaking views with an indoor private pool, come escape with us
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Middletown
The price is AU$504 per night from 6 Jan to 7 Jan
AU$504
includes taxes & fees
6 Jan - 7 Jan 2025
When you stay at this vacation home in Middletown, you'll be within a 10-minute drive of Orchid Cellar Winery and Willow Oaks Craft Cider and Wine.
Charming "Cream of the Crop" Cape ~❤️of Middletown
Cozy townhome with WiFi and AC in charming Sterling

Cozy townhome with WiFi and AC in charming Sterling

Sterling
The price is AU$193 per night from 24 Dec to 25 Dec
AU$193
includes taxes & fees
24 Dec - 25 Dec
With a stay at this vacation home in Sterling, you'll be within a 15-minute drive of Reston Town Center and Seneca Square Shopping Center.
Cozy townhome with WiFi and AC in charming Sterling
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Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
The price is AU$1,035 per night from 26 Dec to 27 Dec
AU$1,035
includes taxes & fees
26 Dec - 27 Dec
With a stay at this vacation home in Charles Town, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and Shenandoah ...
Terra Alta - Incredible River Views and Hot Tub!
 Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Marshall
Located in Marshall, this vacation home is in a rural location, within a 10-minute drive of Upperville Park and National Sporting Library & Museum.
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated  Sunny Luxurious Indoor

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Middleburg
Located in Middleburg, this vacation home is in a rural location, a 5-minute drive from Greenhill Winery & Vineyards and 5 minutes from Red Fox Fine Art.
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Appalachian Trail Conservancy ...
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!
Riverside cottage, minutes from historic Harpers Ferry!  Private river access!

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Harpers Ferry
The price is AU$356 per night from 26 Dec to 27 Dec
AU$356
includes taxes & fees
26 Dec - 27 Dec
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Potomac River and within a 5-minute drive of Chesapeake and Ohio Canal.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and John Brown Wax ...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
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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.

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

Holiday houses in Dickerson 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 Dickerson 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 Dickerson adventures, obvs.

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

Dickerson Holiday Homes essential information

Accommodation
372 Holiday Homes
Lowest Price
AU$145
Highest Price
AU$1,035
Popular accommodation
Breathtaking views with an indoor private pool, come escape with us, Charming "Cream of the Crop" Cape ~❤️of Middletown, Cozy townhome with WiFi and AC in charming Sterling, Terra Alta - Incredible River Views and Hot Tub!, Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor, Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!, Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Top trending hotels in Dickerson

Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is AU$201 per night from 10 Jan to 11 Jan
AU$201
includes taxes & fees
10 Jan - 11 Jan 2025
When you stay at Hyatt Regency Dulles in Herndon, you'll be next to a golf course, within a 15-minute drive of Reston Town Center and Dulles Expo Conference ...
Hyatt Regency Dulles
Embassy Suites by Hilton Tysons Corner

Embassy Suites by Hilton Tysons Corner

3.5 out of 5
8517 Leesburg Pike, Vienna, VA
Fully refundableReserve now, pay when you stay
The price is AU$145 per night from 3 Jan to 4 Jan
AU$145
includes taxes & fees
3 Jan - 4 Jan 2025
When you stay at Embassy Suites by Hilton Tysons Corner in Vienna, you'll be in the business district, within a 15-minute drive of Tysons Corner Center and Reston ...
Embassy Suites by Hilton Tysons Corner
The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

4 out of 5
8120 Wisconsin Ave, Bethesda, MD
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 29 Dec to 30 Dec
AU$187
includes taxes & fees
29 Dec - 30 Dec
Located in Bethesda, The Bethesdan Hotel, Tapestry Collection by Hilton is in the business district, within a 5-minute drive of Walter Reed National Military ...
The Bethesdan Hotel, Tapestry Collection by Hilton
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Embassy Suites by Hilton Bethesda Washington DC

Embassy Suites by Hilton Bethesda Washington DC

3.5 out of 5
6711 Democracy Blvd, Bethesda, MD
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 30 Dec to 31 Dec
AU$216
includes taxes & fees
30 Dec - 31 Dec
With a stay at Embassy Suites by Hilton Bethesda Washington DC in Bethesda, you'll be in the business district, within a 15-minute drive of Tysons Corner Center ...
Embassy Suites by Hilton Bethesda Washington DC
Don't see what you're looking for?
See all available properties in Dickerson
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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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^Subject to availability and chosen travel dates.