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Woodstock Rentals

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160 Houses

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

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$365

Tentrr Signature Site - The Perch

Woodstock tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$149

Great rentals within 20 miles that match your search

☆ SKI ON & OFF! ☆ Luxury Trailside Condo! NEW Steam Shower, Hot Tub, Pool

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

“First Family Ski Trip with the Kids” I have a 4 year old and an 11 month old and neither my wife nor I had been skiing since both kids were born. Our eldest was ready for his first skiing vacation and Killington was a great spot since they have a great ski school and child care for the little one. We booked somewhat late but had another couple that wanted to bring their 4 year old daughter as well, so we found this awesome rental. Unfortunately we didn't really get to use the ski on/off to its fullest potential since we had to drop the kids off at their base each day but it would have been extremely convenient. The condo was the perfect size, wifi was key along with the other amenities. The clubhouse was close and convenient, awesome to be able to take the kids to the pool after a day on the slopes and sit myself in the hot tub while they played. I will definitely be coming back here!

Responds fast! avg. 12 minutes

Price per night from

$196

Ski Killington Vermont

Killington apartment

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$248

Luxury Lakefront Home near Okemo

Ludlow house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$842

Hidden House Vermont : Private Mountain Retreat in the Heart of The Green Mts.

Bethel apartment

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$301

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

Mount Holly private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

Chase House Inn - Edwin Stanton Room

Cornish house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$187

Heavenly Vacation Home on Silver Lake

Barnard house

5 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$608

Elegant victorian with free wifi, private washer/dryer - Near Okemo

Proctorsville house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$483

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

15 bedrooms / 12 bathrooms / sleeps 44

Price per night from

$6,420

Hideaway Chalet Comfort for 24 SKI PASSES 50% ski slopes 2min HOT TUB

Killington house

8 bedrooms / 6 bathrooms / sleeps 24

Responds fast! avg. 1 hour 56 minutes

Price per night from

$1,185

Price per night from

$309

Mountain dog-friendly duplex w/ firepit, pellet grill & deck - close to Okemo

Ludlow townhouse

4 bedrooms / 1 bathroom / sleeps 14

Price per night from

$296

Serene & Private 20acre Mountain Getaway!

Bethel house

3 bedrooms / 3 bathrooms / sleeps 21

Price per night from

$695

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

4 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$753

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

Killington house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$289

Ski House Between Killington and Okemo

Plymouth condo

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 13 minutes

Price per night from

$257

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 my Granddaughter will be attending VLS starting in the Fall.

Responds fast! avg. 2 hours 14 minutes

Price per night from

$170

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

$513

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

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$743

A Vermont House for All Seasons

Ludlow cottage

3 bedrooms / 2 bathrooms / sleeps 6

“Perfect, just PERFECT” This house is just perfect for my group of 6. Everything is exactly as described. It's clean, warm & cozy, has everything that you need. Owner is very nice & thoughtful as well, you can find little notes throughout the house. Could not have asked for more!

Responds fast! avg. 2 hours 15 minutes

Price per night from

$261

2 bedroom premium AAA rated condo across from the slopes-2D2

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$225

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$431

Ski-in/out Luxury 3 Bedroom & 3 Bathroom Okemo Penthouse Condo at Jackson Gore

Ludlow apartment

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,479

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

6 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$282

Cozy Apt Near Killington Ski Area & Sugarbush Farm

Bridgewater apartment

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 15 minutes

Price per night from

$181

2 bedroom premium AAA rated condo across from the slopes-2C4

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 17 minutes

Price per night from

$219

South Face Village

Ludlow condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$616

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!

Responds fast! avg. 1 hour 34 minutes

Price per night from

$951

2 mins to Okemo, Shuttle Route and Hot Tub!

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 7 minutes

Price per night from

$174

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$309

Clifford Country Bed & Breakfast, open May-October

Mount Holly b&b

3 bedrooms / 2 bathrooms / sleeps 6

“Unspoiled Vermont at it's finest!” Located on a quiet country lane in the picturesque little village of Mount Holly Vermont the traveller to the Okemo Valley region will discover the charmingly delightful Clifford Country Bed and Breakfast. The Inn is owned and operated by a lovely women named Emily Clifford Jackson and quite honestly the only thing nicer than your stay at the Inn itself will be the opportunity to meet and become friends with Ms. Jackson. Clifford Country offers it's quests all the warmth and amenities of a country inn including extremely clean and comfortable accommadations complete with old-fashioned home-style hospitality and affordable rates. Breakfast is served daily and features all the old favorites such as fresh fruit and juices, farm fresh milk ,eggs and maple syrup from the farms of local friends and neighbors. Emily also offers a wide variety of freshly home made breads, muffins, pancakes, etc. all of which seem to just be the perfect way to start off your Vermont morning. This was my second visit to Clifford Country and although there is much more that I could tell folks about both the area and the Inn I would like to share this with the viewers of Tripadvisor. As a "Green Hotel in the Green Mountain State" for the traveller looking to experience the epitome of "unspoiled Vermont" Clifford Country is an absolute gem and typifies all that is special about this beautiful place. I suspect there may be places to stay in Vermont that are more pretentious than Clifford Country but I can guarantee there are non more pleasurable. Clifford Country is a totally charming B & B run by an equally charming owner and it really doesn't get any better than that. I shall return to Clifford Country as soon as possible.

Price per night from

$116

KILLINGTON GOLFING, BIKING SKI 2 Bd 1&1/2 B $79 av nt. 4 Season Resort Sleeps 6

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 39 minutes

Price per night from

$106

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

$449

Vermont Cottage Lake Amherst

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$788

Mountain Lodge at Okemo-1Br Newly Renovated

Ludlow condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Price per night from

$173

1Br Ski-in, Ski-out With King Bed- Okemo Mtn Lodge

Ludlow condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Price per night from

$173

Viewing 38 of 160
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.

Also consider