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Holiday Lettings
> North America
> United States
> Vermont
> Houses and Cottages in Woodstock

Houses in Woodstock and Cottages – Holiday Lettings - Holiday Rentals Woodstock

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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39 Holiday homes

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Holiday b&b rental

Woodstock b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £182 / night

£1,273 / week

1 / 27

Ski home to rent in Woodstock

Woodstock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from £336 / night

£2,351 / week

1 / 30

Woodstock holiday home rental

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £229 / night

£1,597 / week

1 / 26

Ski cottage to rent in Woodstock

Woodstock cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £185 / night

£1,290 / week

1 / 18

Woodstock ski apartment to rent.

Woodstock apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £187 / night

£1,307 / week

1 / 24

Ski apartment to rent in Woodstock

Woodstock apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £180 / night

£1,257 / week

1 / 10

Ski apartment to rent in Woodstock

Woodstock apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £108 / night

£754 / week

1 / 23

Ski cottage to rent in Woodstock

Woodstock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £141 / night

£983 / week

1 / 30

Ski home to rent in Woodstock

Woodstock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £292 / night

£2,044 / week

1 / 30

Woodstock ski home to rent.

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £301 / night

£2,102 / week

1 / 23

Woodstock ski home to rent.

Woodstock house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 6

from £439 / night

£3,071 / week

1 / 27

Ski home to rent in Woodstock

Woodstock house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £241 / night

£1,681 / week

1 / 30

Holiday home in Taftsville

Taftsville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £304 / night

£2,122 / week

1 / 30

Woodstock ski home to rent.

Woodstock house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from £572 / night

£4,004 / week

1 / 20

Holiday home in Woodstock

Woodstock house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £519 / night

£3,630 / week

1 / 16

Woodstock ski home to rent.

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,179 / night

£8,248 / week

1 / 30

Woodstock holiday home let

Woodstock house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

from £859 / night

£6,008 / week

1 / 30

Woodstock ski chalet to rent.

Woodstock chalet

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £201 / night

£1,407 / week

1 / 30

Ski home to rent in Woodstock

Woodstock house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £310 / night

£2,167 / week

1 / 24

Home rental in Woodstock

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £316 / night

£2,212 / week

1 / 15

Holiday home rental

Taftsville house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from £555 / night

£3,881 / week

1 / 30

Woodstock ski home to rent.

Woodstock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £288 / night

£2,011 / week

1 / 30

Home rental in Woodstock

Woodstock house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from £2,194 / night

£15,356 / week

1 / 27

Ski home to rent in Woodstock

Woodstock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £678 / night

£4,741 / week

1 / 30

Holiday home in Woodstock

Woodstock house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £120 / night

£838 / week

1 / 11

Holiday cottage in Woodstock

Woodstock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £158 / night

£1,106 / week

1 / 30

Woodstock ski home to rent.

Woodstock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £357 / night

£2,496 / week

1 / 28

Holiday home in Woodstock

Woodstock house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £120 / night

£838 / week

1 / 11

Ski home to rent in Woodstock

Woodstock house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £421 / night

£2,943 / week

1 / 30

Woodstock holiday home rental

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

from £280 / night

£1,955 / week

1 / 18

Woodstock ski home to rent.

Woodstock house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £252 / night

£1,759 / week

1 / 30

Ski home to rent in Woodstock

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £395 / night

£2,764 / week

1 / 30

Ski home to rent in Woodstock

Woodstock house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £300 / night

£2,094 / week

1 / 30

Ski home to rent in Woodstock

Woodstock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £239 / night

£1,671 / week

1 / 27

Ski home to rent in Woodstock

Woodstock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £180 / night

£1,257 / week

1 / 16

Woodstock ski cottage to rent.

Woodstock cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £402 / night

£2,815 / week

1 / 30

Woodstock holiday home rental

Woodstock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £627 / night

£4,384 / week

1 / 30

Cottage rental in Woodstock

Woodstock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Pricing unknown

1 / 8

Woodstock holiday home rental

Woodstock house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £599 / night

£4,188 / week

1 / 17

Great rentals within 20 miles that match your search

Ski home to rent in Killington

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

from £868 / night

£6,074 / week

1 / 53

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Woodstock holidays

With numerous options for outdoor recreational activities, interesting historical sites, and friendly locals, the Vermont town of Woodstock has it all! Central Street is the primary commercial shopping district in Woodstock, but you can also visit The Green for some of the best restaurants that the state has to offer.

Here are a few additional suggestions of things to do in Woodstock:

  • Billings Farm and Museum: Visit this 270 acre farm, dairy barn, and museum with historic artefacts.
  • Ottauquechee River: This river that runs through Woodstock offers plenty of opportunities for fishing and canoeing excursions.
  • Dana House: This small museum hosts several pieces of artwork and historic artefacts from the local area in the 19th century.
  • Mount Tom: Climb to the top of Woodstock's main mountain for stunning views of the town and surrounding areas.

There are many events and festivals held throughout the year in Woodstock that bring the whole community together. Watch the parade through town featuring horses and costumed riders during Wassail weekend in February, sample artwork from the top painters and sculptors in the region during the Woodstock Art Festival in September, or try the local cuisine from the best chefs and brewers in the state during the Taste of Woodstock event in September.

To get the most out of your time in Woodstock, stay in a holiday rental. Rent a villa or condo close to the historic sites throughout town, or book a cosy cabin with amazing mountain views right outside your door.

If you wish to explore the rest of the region, Woodstock is only a short drive from some of the other popular towns and cities in Vermont. The hiking options found in Rutland and the colonial village of Barre can both be reached within an hour by car.

Also consider