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Woodstock Rentals

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Price range

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$10 - $500

Woodstock Rentals

About Woodstock

324 Houses

Woodstock VT Village Log Home Apartment WINTER WONDERLAND

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 4

“A great way to see Woodstock!” We got married in Woodstock in September of 2012 and decided to take a trip back to explore without the pressure of planning or having a wedding. We normally stayed at the Woodstock Inn, but no longer. The apartment exc

Price per night from

$99

1 / 36

'Lilac Cottage' - Victorian S. Woodstock Retreat!

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 52 minutes

Price per night from

$301

1 / 24

Woodstock Carriage House! Vermont's finest county road with homes and farms.

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$220

1 / 27

Dog-friendly house w/ charm & entertainment - 4 miles to nearest ski slopes!

Woodstock house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 2 minutes

Price per night from

$110

1 / 29

Luxury Apartment Over Brook, Near Village

Woodstock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

1 / 6

Serene, Modern Escape, Overlooking Quiet Brook

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$150

1 / 6

Great rentals within 20 miles that match your search

Sun House Studios

Sharon house

3 bedrooms / 2 bathrooms / sleeps 6

“Above expectations and perfect location for visiting Vermont Law School.” Perfect location for visiting Vermont Law School. Comfortable and all amenities that would be needed are provided. Clean and great attention to detail. Would return now that

Responds fast! avg. 1 hour 48 minutes

Price per night from

$150

1 / 30

Seasonal Rental Cozy 2 BR Apt 5 min drive to Okemo & 25 min drive to Killington

Ludlow apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$100

1 / 10

Cozy country cabins with all the comforts of home!

South Royalton log cabin

2 bedrooms / 1 bathroom / sleeps 3

“A great cozy get away!” My boyfriend and I stayed at the upper cabin last week and it was just what we needed to relax. The cabin is beautifully decorated to make you feel right at home. The gas fire place in the living room really makes the cabin toa

Price per night from

$189

1 / 31

Savage Hart Farm's Two Bedroom Apartment

White River Junction apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$244

1 / 13

Savage Hart Farm - a Sheep Farm with an Apartment

White River Junction apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$164

1 / 12

Ludlow Cabin Near Okemo Ski Lodge

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$249

1 / 27

Premier Ski-in / Ski-out - 3 Bed, Sunrise Mountain

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$647

1 / 28

Okemo Slopeside Rental located at the Main Base!

Ludlow condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$373

1 / 16

The Lodges Bear Mountain Luxury ski-on/ski-off 3 bed 3 Bath LOW RATES-Mar/Apr

Killington condo

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$294

1 / 54

Sunrise - W Glade J-1

Killington apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$232

1 / 24

Spacious Loft Style Apartment on the Green

Strafford apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$174

1 / 17

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$75

1 / 36

6 BR Ski Chalet in VT Green Mountains

Ludlow chalet

6 bedrooms / 2 bathrooms / sleeps 16

Price per night from

$244

1 / 39

Lakeside house, close to Woodstock

Barnard house

5 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 50 minutes

Price per night from

$493

1 / 17

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 1 hour 55 minutes

Price per night from

$493

1 / 29

Pico Resort Slopeside Condo, Killington Vermont

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$125

1 / 38

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$696

1 / 39

NEW! 4-Season Stockbridge Home-Fireplace & Deck!

Stockbridge house

6 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 9 minutes

Price per night from

$319

1 / 33

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 cente

Responds fast! avg. 2 hours 48 minutes

Price per night from

$597

1 / 18

Charming Ski Chalet Close to Main St & Okemo Mtn

Ludlow chalet

3 bedrooms / 2 bathrooms / sleeps 13

Price per night from

$274

1 / 26

Killington Furnished Private Apartment

Killington apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$150

1 / 6

Tanglewood Vista at Killington: Amazing Mountain Vacation Destination!

Killington house

5 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$125

1 / 47

Quiet Hillside 4 Bedroom Carriage House W/3 Baths

Ludlow guest house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$299

1 / 16

Legendary Racquetball Home, Book now for March!

Killington house

5 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$995

1 / 17

Cabin in the Big Woods - sleeping porch lake trails playground

Mount Holly log cabin

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$80

1 / 20

Queen room in peaceful country B&B, open May-Oct.

Mount Holly room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$103

1 / 11

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

7 bedrooms / 4 bathrooms / sleeps 22

Price per night from

$498

1 / 20

Premier Ski-in/Ski-out Location, Sunrise Mountain

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$324

1 / 24

Cricket Hill - Cozy, clean, private, spacious. 5 rooms. Entire lower level.

Killington house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$130

1 / 19

Walk to Okemo Ski Lifts! Private 5 bedroom home.

Ludlow house

5 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 2 hours 18 minutes

Price per night from

$224

1 / 25

Luxury Lake Rescue Home Near Okemo

Ludlow house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$498

1 / 24

NEW! Pristine Home Near Suicide Six & DT Woodstock

South Pomfret house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 35 minutes

Price per night from

$269

1 / 24
Viewing 38 of 324

About Woodstock

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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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