Book Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock

Secluded River Cabin Getaway (Masten Cabin)

Secluded River Cabin Getaway (Masten Cabin)

Strasburg
With a stay at this vacation home in Strasburg, you'll be in the mountains, just a 1-minute walk from George Washington National Forest and 10 minutes by foot ...
Secluded River Cabin Getaway (Masten Cabin)
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Edinburg
When you a stay at this vacation home in Woodstock, you'll be on a river, just steps from George Washington National Forest and Shenandoah River.
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Rileyville
With a stay at this vacation home in Rileyville, you'll be on the waterfront, within a 15-minute drive of Luray Caverns and Warehouse Art Gallery.
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
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Charming Farmhouse w King Bed Hot Tub & EV Charger

Charming Farmhouse w King Bed Hot Tub & EV Charger

Timberville
When you stay at this vacation home in Timberville, you'll be in the mountains, within a 5-minute drive of New Market Community Park and The Shenvalee Golf ...
Charming Farmhouse w King Bed Hot Tub & EV Charger
Cozy Lakeside Homestead

Cozy Lakeside Homestead

Wardensville
When you stay at this vacation home in Wardensville, you'll be on a lake and steps from Warden Lake.
Cozy Lakeside Homestead
Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views

Strasburg
Located in Strasburg, this vacation home is within a 5-minute drive of George Washington National Forest and Shenandoah River.
Newly renovated Farm cottage with Mountain views
Hot Tub, Fire Pit, Grill, Screened Porch & WiFi

Hot Tub, Fire Pit, Grill, Screened Porch & WiFi

Mount Jackson
Located in Mount Jackson, this vacation home is within a 15-minute drive of Bryce Ski Resort and George Washington National Forest.
Hot Tub, Fire Pit, Grill, Screened Porch & WiFi
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

Luray
When you stay at this vacation home in Luray, you'll be steps from George Washington National Forest.
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!
Historic Slate Hill School House in Fort Valley, Virginia

Historic Slate Hill School House in Fort Valley, Virginia

Fort Valley
With a stay at this vacation home in Fort Valley, you'll be in the mountains, just steps from George Washington National Forest and a 4-minute drive from Secret ...
Historic Slate Hill School House in Fort Valley, Virginia
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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.

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

Holiday houses in Woodstock 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 Woodstock 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 Woodstock adventures, obvs.

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

Woodstock Holiday Homes essential information

Accommodation
325 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Secluded River Cabin Getaway (Masten Cabin), Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub, Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Charming Farmhouse w King Bed Hot Tub & EV Charger, Cozy Lakeside Homestead, Newly renovated Farm cottage with Mountain views , Hot Tub, Fire Pit, Grill, Screened Porch & WiFi, Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP! , Historic Slate Hill School House in Fort Valley, Virginia

Top trending hotels in Woodstock

Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 out of 5
1011 Motel Dr, Woodstock, VA
Comfort Inn Woodstock Shenandoah is centrally located in Woodstock, a 3-minute walk from Shenandoah County Fairgrounds and a 3-minute drive from Shenandoah ...
Comfort Inn Woodstock Shenandoah
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

2.5 out of 5
1130 Motel Dr, Woodstock, VA
Fully refundable
Located in Woodstock, Holiday Inn Express Woodstock-Shenandoah Valley by IHG is within a 5-minute drive of Shenandoah County Fairgrounds and W.O. Riley ...
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA

2.5 out of 5
1150 Motel Dr, Woodstock, VA
Fully refundableReserve now, pay when you stay
Located in Woodstock, Hampton Inn & Suites Woodstock, VA is within a 5-minute drive of Shenandoah County Fairgrounds and W.O. Riley Park.
Hampton Inn & Suites Woodstock, VA
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Econo Lodge Woodstock - Shenandoah Valley I-81

Econo Lodge Woodstock - Shenandoah Valley I-81

2 out of 5
1290 S Main St, Woodstock, VA
Fully refundableReserve now, pay when you stay
When you stay at Econo Lodge Woodstock - Shenandoah Valley I-81 in Woodstock, you'll be in the mountains, within a 5-minute drive of Shenandoah County Fairgrounds ...
Econo Lodge Woodstock - Shenandoah Valley I-81
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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.