Book Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the ...
Opens in a new windowTraveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 5-minute drive of Okemo Mountain Resort and Red Lot.
Opens in a new windowClassic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Quiet Modern Luxury Home w/  Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater
With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing ...
Opens in a new windowQuiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
77 Okemo Ridge Rd, Ludlow, VT
With a stay at Okemo Mountain Lodging in Ludlow (Clock Tower Base Area), you'll be within a 10-minute walk of Okemo Mountain Resort and General Parking.
Opens in a new windowOkemo Mountain Lodging
Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

Hartford
Located in White River Junction, this vacation home is on a river, within a 15-minute walk of The Strong House Spa and Route 4 Glassblowing Studio.
Opens in a new windowBeautifully renovated with fireplace and coffee bar
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Ludlow
When you stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute walk of Okemo Mountain Resort and Sunshine Ski Lift.
Opens in a new windowClassic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Killington
With a stay at this vacation home in Killington, you'll be in the mountains, within a 10-minute drive of Killington Resort and Green Mountain National ...
Opens in a new windowSpacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Killington Vermont Ski and Snowmobiling House

Killington Vermont Ski and Snowmobiling House

Pittsfield
With a stay at this vacation home in Pittsfield, you'll be within a 15-minute drive of Killington Resort and Green Mountain National Forest.
Opens in a new windowKillington Vermont Ski and Snowmobiling House
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village ...
Opens in a new windowSki-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
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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
817 Holiday Homes
Lowest Price
AU$381
Highest Price
AU$604
Popular accommodation
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Okemo Mountain Lodging, Beautifully renovated with fireplace and coffee bar, Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table, Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking, Killington Vermont Ski and Snowmobiling House, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Top trending hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$604 per night from 30 Nov to 1 Dec
AU$604
30 Nov - 1 Dec
includes taxes & fees
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
Opens in a new windowWoodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
Opens in a new windowThe Shire Woodstock
The Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
Located in Woodstock (West Woodstock), The Jackson is within a 5-minute drive of Union Arena Community Center and Five Elm Arches.
Opens in a new windowThe Jackson
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On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is AU$381 per night from 10 Nov to 11 Nov
AU$381
10 Nov - 11 Nov
includes taxes & fees
Located in Woodstock (West Woodstock), On The River Inn is within a 5-minute drive of Union Arena Community Center and Five Elm Arches.
Opens in a new windowOn The River Inn
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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.