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

$490

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

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,093

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$374

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

Price per night from

$5,116

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$288

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

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

$978

Ski Killington Vermont

Killington apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Price per night from

$219

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$432

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

Price per night from

$748

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

$460

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

$863

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$403

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

$633

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

$288

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

$459

Price per night from

$190

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$167

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

$363

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$213

Price per night from

$1,380

Suites at killington Center

Killington condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$345

Vermont Cottage Lake Amherst

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$805

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$805

Pico Resort Slopeside Condo, Killington Vermont

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$518

Price per night from

$403

Quintessential Guest House Getaway

Meriden guest house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$546

25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails

Ludlow apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$403

Killington - FALL IN THE MOUNTAINS...YOU CAN'T BEAT THE VIEWS!

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$259

Clean/Comfortable 2 Bdroom Cabin w/No Hidden Fees*

Mendon house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$206

“The Perfect Vermont Getaway” When I visit Vermont in winter, I tend to go with a mixed crowd. Part of our group are avid skiers/snowboarders, the other part (well, me) are not. This house allows you to experience the best of both worlds, with something for everyone. Situated on top of the mountain (within walking distance to the lodge and with a shuttle that can pick you up right outside the front door), it's in the absolute perfect location for those who like to lace up their boots and hit the slopes. For anyone not playing snow bunny for the day, you are smack dab in the middle of Okemo with plenty of cafes, shopping, and scenic walks just down the hillside (or a very short drive away if you wish to explore). The house itself is also a fantastic, light, open space that is comfortable no matter which straw you draw for beds (we got the twins in the upstairs loft and had one of the soundest sleeps I'd had all winter). Plus, who doesn't love a hot tub. You never feel cramped even with a full house. The living room is an amazing space to just sip coffee and read your book in the morning sunshine or in front of the fire. The owners are extremely knowledgeable, responsive, and helpful, and made sure our stay was top-notch. They have everything outlined for you in a book when you arrive and are there for you should you have any questions. I can't wait to go back next winter!

Price per night from

$1,840

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$1,374

☆ SKI ON & OFF! ☆ Spruce Glen C on Great Eastern Trail w/Sauna, Fireplace

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 9 minutes

Price per night from

$95

Viewing 38 of 108
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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