Woodstock Rentals

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Stay At Jimmy's

Woodstock b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$229

Great rentals within 20 miles that match your search

Price per night from

$489

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$167

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$373

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

Price per night from

$5,107

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$287

Killington Mountain Slopeside Home

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Ski home at Killington” We've been here for 10 days in late January. Wonderful place. Excellent home. We were two families with 4 aDT, CHD 4 with 6.9, 11 and 14 years. We left and came back home from skiing. We used the heated pool at the sport center. the hot tub ... We skate on the frozen pond. Although we are not accustomed to the cold (-13 F/ -25 C) for being Brazilians, we enjoyed a lot. Thank you!

Price per night from

$976

Ski Killington Vermont

Killington apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Price per night from

$218

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$431

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,091

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$213

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Ludlow townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$459

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Killington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$861

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

Price per night from

$746

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 58 minutes

Price per night from

$104

South Face Village

Ludlow condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$632

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$345

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Reading house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$287

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$402

Price per night from

$190

Chase House Inn - Edwin Stanton Room

Cornish house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$173

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 20

Responds fast! avg. 37 minutes

Price per night from

$458

1820 House

Perkinsville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$345

A Quiet Retreat in Rural New Hampshire

Cornish house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$362

Breakaway House - Unit A & B

Killington house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

Price per night from

$668

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 58 minutes

Price per night from

$104

PennRock Lakeside

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$368

Sunrise Timberline A2 - Ski Shack

Killington condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$378

The Whimsical Chalet

Mount Holly villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$291

Sweet Life

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$367

Mt Green 3-D10

Killington house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$373

Sunrise - W Glade J-1

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$288

Gateway Condominium Unit 25

Mendon condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$149

The Mendon House

Killington house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$287

Mt Green 2-F09

Killington studio

  • Studio
  • 1 bathroom
  • sleeps 4

Price per night from

$163

Woods Village 43

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$269

Mt Green 2-C03

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$258

Woods Village 33

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$180

Viewing 38 of 109
rentals in Woodstock

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About Woodstock

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 artifacts.
  • Ottaquechee 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 artifacts 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 vacation rental. Rent a villa or condo close to the historic sites throughout town, or book a cozy 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.

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