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
Book a stay at this family-friendly vacation home in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and ...
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
Stay at this vacation home in Ludlow. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Okemo Mountain Resort and Sachem ...
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
Stay at this vacation home in Bridgewater Corners. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Long Trail Brewing Company and Coolidge ...
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
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and ...
Opens in a new windowOkemo Mountain Lodging
Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

Hartford
Book a stay at this golf vacation home in White River Junction. Enjoy free WiFi, a fitness center, and a garden. Popular attractions The Strong House Spa and ...
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
Book a stay at this ski vacation home in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Sunshine Ski ...
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
Book a stay at this family-friendly vacation home in Killington. Enjoy free WiFi, a sauna, and a garden. Popular attractions Killington Resort and Fire Tower ...
Opens in a new windowSpacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
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
Book a stay at this ski vacation home in Killington. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Killington Resort and Sunrise ...
Opens in a new windowSki-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Killington
Book a stay at this family-friendly vacation home in Killington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Killington Resort and Black ...
Opens in a new windowMountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
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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
853 Holiday Homes
Lowest Price
NZ$436
Highest Price
NZ$692
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, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Top trending hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$692 per night from 30 Nov to 1 Dec
NZ$692
30 Nov - 1 Dec
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowWoodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowThe Shire Woodstock
The Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
Stay at this 4-star B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions ...
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 NZ$436 per night from 10 Nov to 11 Nov
NZ$436
10 Nov - 11 Nov
includes taxes & fees
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Opens in a new windowOn The River Inn
Don't see what you're looking for?
See all available properties in Woodstock
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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.