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Woodstock Rentals

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308 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 exceeded our expectations - it was spacious, private and full of all the amenities you'd have at your home. Close to everything and walkable to downtown, owners who are personable and knowledgeable of the area you can't find a better place to launch your exploration of Woodstock!

Price per night from

$114

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

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$255

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

Woodstock house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$289

Luxury Apartment Over Brook, Near Village

Woodstock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$290

Serene, Modern Escape, Overlooking Quiet Brook

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$261

Stunning home with pool table, dart board, & gas grill!

Taftsville house

5 bedrooms / 5 bathrooms / sleeps 9

Price per night from

$310

Tentrr Signature - The Perch

Woodstock tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$180

Great rentals within 20 miles that match your search

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

Proctorsville house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 1 minutes

Price per night from

$452

Cozy Historic Hilltop Cottage

Brownsville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$167

Heavenly Vacation Home on Silver Lake

Barnard house

5 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$570

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

Killington house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$634

Great Bear Lodge

Sharon house

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$403

Minutes from Killington + Okemo + Woodstock, VT come and experience The Cabin

Bridgewater log cabin

4 bedrooms / 3 bathrooms / sleeps 24

Price per night from

$924

☆ 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

$174

2 mins to Okemo, Shuttle Route and Hot Tub!

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 13 minutes

Price per night from

$145

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

15 bedrooms / 12 bathrooms / sleeps 44

Price per night from

$2,829

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

$462

Heavenly on Killington Access Road Brand New House

Killington house

7 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$635

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

Killington house

8 bedrooms / 6 bathrooms / sleeps 24

Responds fast! avg. 3 hours 5 minutes

Price per night from

$1,018

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

$120

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. 3 hours 8 minutes

Price per night from

$694

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 12 minutes

Price per night from

$105

Colonial-style solid-timber home in a quiet setting; sanctuary.

Barnard house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$278

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

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$752

Ski Killington, Pico, Snow Mobile, Summer Fun

Killington house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$579

Swiss Chalet 8-Bdrooms_6 F-Bathrooms X-Mass *Grps 5+

Killington chalet

8 bedrooms / 6 bathrooms / sleeps 22

Price per night from

$579

South Face Village

Ludlow condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$637

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

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$226

Oma"s Kottage

Ludlow house

6 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 25 minutes

Price per night from

$232

KILLINGTON GOLFING, BIKING SKI 2 Bd 1&1/2 B $79 av nt. 4 Season Resort Sleeps 8

Killington condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 49 minutes

Price per night from

$111

Vermont Cottage Lake Amherst

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$810

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 3 hours 20 minutes

Price per night from

$434

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

Mount Holly private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$120

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$62

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

Ludlow condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$261

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

$342

Clean, Affordable, 2 BR Apt 5 min drive to Okemo & 25 min drive to Killington Mt

Ludlow apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$87

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$810

Viewing 38 of 308
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.

Top Destination reviews

Woodstock VT Village Log Home Apartment WINTER WONDERLAND
Great weekend stay

I book this place for my wife and I to stay at while i raced the Vermont Overland bike race. Unfortunately l, she was unable to join me do a last minute issue. Having been committed to riding I went up alone. The owner, Bob, was very accommodating. I also had a buddy who was racing stay the night before the race to save him the long drive I the morning. The place was bright, extremely well keep and comfortable. It's best appeal is the location within an easy walk to town. Overall a great experience for a weekend get away.see more
Woodstock Carriage House! Vermont's finest county road with homes and farms.
Beautiful home away from home.

Arriving on Cloudland Rd and staying at the Carriage House was a wonderful experience. The beauty of Woodstock and and its surroundings made this home a special place to stay. In addition, Margarete's hospitality was as warm and welcoming as you can hope for. I look forward to returning again in the future!see more

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