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Woodstock Vacation Rentals

Find 246 available offers from 7 partners
Woodstock
Anytime
Guests
Woodstock
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Woodstock

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

Embrace the natural beauty of Vermont with a Woodstock vacation rental

A vacation rental in Woodstock will position you to embrace the outdoors, where you can enjoy everything from skiing and snowboarding in the winter months to hiking and swimming during warmer temperatures. Cottages, wood cabins and turn of the century farmhouses are all typical types of Woodstock, Vermont vacation homes.

Show all 247 properties

Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Woodstock rental with full kitchen.

House  Woodstock
Dec 29 - Jan 5
$849 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Village Of Woodstock with Grill, Yard & Pool + Mountain Views

5.0
Outstanding (13 ratings)
Woodstock, Windsor County, Vermont, United States
Kitchen
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Motel  Woodstock
Oct 2 - Oct 9
$479 per night
Motel ∙ 8 guests ∙ 1 bedroom

Motel in Woodstock

4.7
Excellent (328 ratings)
Woodstock, Windsor County, Vermont, United States
Kitchen
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Bed and breakfast  Woodstock
Dec 29 - Jan 5
$214 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wonderful B&B in Village Of Woodstock

Woodstock, Windsor County, Vermont, United States
Kitchen
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Woodstock and book a vacation rental with air conditioning.

House  Woodstock
Oct 2 - Oct 9
$324 per night
House ∙ 8 guests ∙ 3 bedrooms

Charming House in Woodstock with Grill & Yard

5.0
Outstanding (3 ratings)
Woodstock, Windsor County, Vermont, United States
Air conditioning
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Cottage  Woodstock
Jul 13 - Jul 20
$234 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Village Of Woodstock with Grill & Yard

4.8
Outstanding (90 ratings)
Woodstock, Windsor County, Vermont, United States
Air conditioning
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Chalet  Woodstock
Nov 16 - Nov 23
$253 per night
Chalet ∙ 6 guests ∙ 2 bedrooms

Modern Chalet in Woodstock with Finnish Sauna

5.0
Outstanding (76 ratings)
Woodstock, Windsor County, Vermont, United States
Air conditioning
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Woodstock accommodation with high-speed internet.

Cottage  Woodstock
Oct 18 - Oct 25
$176 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Woodstock with Yard, Grill & Patio + Gorgeous Views

5.0
Outstanding (51 ratings)
Woodstock, Windsor County, Vermont, United States
Internet
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House  Woodstock
Jun 30 - Jul 7
$410 per night
House ∙ 6 guests ∙ 4 bedrooms

Beautiful House in Woodstock with Grill, Patio & Yard

5.0
Outstanding (85 ratings)
Woodstock, Windsor County, Vermont, United States
Internet
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Farmhouse  Woodstock
Jun 30 - Jul 7
$315 per night
Farmhouse ∙ 8 guests ∙ 4 bedrooms

Farm in Woodstock with Yard & Grill + Vineyard Views

5.0
Outstanding (34 ratings)
Woodstock, Windsor County, Vermont, United States
Internet
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Best Vacation Home Deals in Woodstock

Save up to 47%

Bed and breakfast Woodstock
Jun 22 - Jun 29
-29%
$371
$264 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed And Breakfast in Village Of Woodstock with Patio & Yard

Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Jul 6 - Jul 13
-47%
$1,025
$542 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort in Village Of Woodstock with Outdoor Pool

4.9
Outstanding
Woodstock, Windsor County, Vermont, United States
Free cancellation
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House Woodstock
Dec 29 - Jan 5
-16%
$415
$350 per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful House in Woodstock with Grill, Patio & Yard + Beautiful Views

5.0
Outstanding (58 ratings)
Woodstock, Windsor County, Vermont, United States
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Find a rental meeting your expectations among the 246 great vacation rentals from numerous partner websites in Woodstock. HomeToGo immediately compares all of these properties so you can save up to 47%!

Recommended Vacation Rentals in Woodstock

Find your perfect vacation rental in Woodstock: from $140 per night

House Woodstock
Oct 2 - Oct 9
$362 per night
House ∙ 7 guests ∙ 3 bedrooms

Whole Vacation Home in Woodstock with Yard, Grill & Pool

5.0
Outstanding (34 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Jun 29 - Jul 6
$360 per night
House ∙ 6 guests ∙ 3 bedrooms

Charming House in Woodstock with Yard, Patio & Grill

5.0
Outstanding (26 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Aug 10 - Aug 17
$686 per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home in Woodstock with Patio, Yard & Grill

5.0
Outstanding (22 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Oct 2 - Oct 9
$854 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful Vacation Home in Woodstock with Yard, Grill & Patio

5.0
Outstanding (31 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Jul 27 - Aug 3
$1,668 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Woodstock with Yard, Grill & Patio + Natural Views

5.0
Outstanding (22 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Oct 2 - Oct 9
$826 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful Vacation Home in Village Of Woodstock with Grill, Patio & Sauna + Amazing Views

5.0
Outstanding (2 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Aug 3 - Aug 10
$400 per night
House ∙ 7 guests ∙ 4 bedrooms

Vacation Home in South Woodstock with Outdoor Fireplace

4.9
Outstanding (245 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Oct 2 - Oct 9
$904 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Village Of Woodstock with Patio & Grill + Sweeping Views

4.9
Outstanding (46 ratings)
Woodstock, Windsor County, Vermont, United States
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Cottage Woodstock
Oct 2 - Oct 9
$774 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Woodstock with Patio & Grill

Woodstock, Windsor County, Vermont, United States
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Budget-friendly Vacation Rentals in Woodstock

Find Fantastic yet Inexpensive Offers

Resort Woodstock
Dec 29 - Jan 5
$614 per night
Resort ∙ 4 guests ∙ 1 bedroom

Lovely Resort in Village Of Woodstock with Jacuzzi, Pool & Yard + Low-Height View

4.6
Excellent (431 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Oct 2 - Oct 9
$503 per night
House ∙ 8 guests ∙ 3 bedrooms

Pleasant House in Woodstock + Beautiful Views

Woodstock, Windsor County, Vermont, United States
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House Woodstock
Oct 2 - Oct 9
$754 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Woodstock with Grill, Patio & Yard + Incredible Views

Woodstock, Windsor County, Vermont, United States
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Top-Rated Rentals and Accommodations in Woodstock

Book Vacation Rental Offers with the Highest User Rating

Resort Woodstock
Dec 29 - Jan 5
$1,054 per night
Resort ∙ 3 guests ∙ 1 bedroom

Resort in Village Of Woodstock with Sauna, Jacuzzi & Patio

4.6
Excellent (431 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Dec 29 - Jan 5
$1,054 per night
Resort ∙ 2 guests ∙ 1 bedroom

Wonderful Resort in Village Of Woodstock with Patio, Pool & Sauna

4.6
Excellent (431 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Dec 29 - Jan 5
$644 per night
Resort ∙ 4 guests ∙ 1 bedroom

Resort in Village Of Woodstock with Yard, Sauna & Pool

4.6
Excellent (431 ratings)
Woodstock, Windsor County, Vermont, United States
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Popular Rental Amenities in Woodstock

  • Pet-friendly (26)
  • Fireplace (140)
  • Pool (92)
  • TV (216)
  • WiFi (236)
  • Fishing (95)
  • Kitchen (62)
  • Air conditioning (237)
  • Washing machine (31)
  • Hot tub (47)
  • No smoking (245)
  • Parking (26)

Above, you can find the most frequently used filters in Woodstock and the number of properties that include them. Woodstock is the right destination to book a rental if you are looking for a pet-friendly rental or you want a rental with a fireplace, as the most frequently offered amenities are "Pets allowed" and "Fireplace." It is also possible to find a property in Woodstock if you need wheelchair access as 77 of the listed accommodations there provide "Wheelchair accessible."

The Weather in Woodstock

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12 days 12
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37°
23°
19 days 19
Jan.
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Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Woodstock climate diagram. In the next 6 months, July will have higher average temperatures. January is the coolest month, with average minimal temperature reaching 12°. The rainiest month is December while the driest month is September.

7-Day Weather Forecast in Woodstock

Fri, 14 Jun
78°
77°

0%

3 h

8 mi/h

Sat, 15 Jun
66°
62°

0%

6 h

11 mi/h

Sun, 16 Jun
71°
68°

10%

1 h

3 mi/h

Mon, 17 Jun
75°
64°

15%

0 h

4 mi/h

Tue, 18 Jun
91°
87°

10%

3 h

7 mi/h

Wed, 19 Jun
91°
89°

10%

5 h

6 mi/h

Thu, 20 Jun
95°
84°

5%

3 h

1 mi/h

Accommodations for your vacation in Woodstock

In Woodstock, bed and breakfast rental are the most common type of accommodation. Additionally, these accommodations have an average size of 27 m² as well as a median price of $340 a night. Furthermore, these rentals are perfect if you're going in a group of 2, it represents the average number of guests bed and breakfast rental can welcome in Woodstock. You can also search and find other accommodation options in Woodstock. House rental are, for example, another popular property type in this destination, with 22 offers to compare. These accommodations cost $760 a night on average and have an average size of 240 m².
Where to find the best food in Woodstock?

Farm-to-Table takes is the star of Woodstock cuisine

New England is famous for its fresh seafood, especially along coastal cities like Boston, but Woodstock Vermont offers farm-fresh options that stand out amongst other inland dining options. Mangalitsa is a newcomer to the Vermont food scene and has high quality foods served in a stylish, wooden interior. The restaurant is known for its remarkable hospitality, seasonal small plates, and their quirky wine list.

Every Friday and Saturday Cloudland Farm serves a farm-to-table dinner featuring a set menu of 2-3 courses. This BYOB restaurant’s menu contains items that are all locally raised and can even be tailored to vegetarian and vegan diets.

Vermont doesn’t exactly conjure up notions of the Caribbean, but Melaza Bistro is changing that. Their fresh ingredients leverage tropical flavors and their menu combines classic New England dishes with bolder nuances to create masterpieces like rum guava glazes, chimichurri steak, and fried green plantains.

What are the best activities for families in Woodstock?

Farms and science museums are fun for the entire family

Despite the name, Suicide Six is a family friendly ski resort that’s suitable for a wide range of abilities and ages. With 30% beginner, 40% intermediate and 30% advanced slopes, the entire family can enjoy Vermont’s snow-covered mountains. In addition to skiing, the resort offers snowboarding, and during warmer months, you can mountain bike, hike, or go fly-fishing.

Billings Farm is an operational and educational farm located just a short stroll from Woodstock. Take in the farm life exhibits and visit the livestock barns that house sheep, horses, and dairy cattle. The restored and fully-furnished farmhouse was originally built in 1890 and features a formal parlor and a creamery in the basement. In the kitchen, you can watch tour guides demonstrate how late 19th century meals would be prepared on the house’s remarkable wood burning stove.

The Montshire Museum of Science is the perfect way to spend the day as a family, especially during inclement weather. Just a 26min drive from Woodstock, the museum focuses on hands-on activities and exhibits. An outdoor area of the museum focuses on water activities and has 100-acres of nature trails.

Where are the unique attractions in Woodstock?

Dreamy day trips: Presidential birthplaces and designer outlets

Weston, VT is about 50 minutes from Woodstock. With its historic Village Green, Weston is listed on the National Register of Historic Places. After wandering the quaint town, you can enjoy a show at the Weston Playhouse; it’s the longest-running professional theater in Vermont, and its team produces classic plays, musicals, and modern works all year long.

Located just 21 minutes south of Woodstock is the birthplace of 30th president Calvin Coolidge. Today the Historic Site includes the Coolidge family homestead but also other buildings including his one-room schoolhouse, a barn, and a cheese factory. Feel free to wander the village at any time, or you can pay for entrance into the buildings along with a guided tour during the from May through October.

For a day of shopping, Manchester designer outlets and fine restaurants are just over an hour away. You’ll find high more than 40 retailers at this outlet center, including high end luggage, designer handbags, kitchenware, and plenty of clothing retailers.

What are the best events and festivals in Woodstock?

Annual festivals highlight the best of Woodstock

Autumn Moon Festival is an annual event held in October, featuring vendors, bouncy castles, face painting, and games. Local historical preservation groups sell wares to raise funds for their organizations, and other vendors display their handcrafted goods including candles, soaps, and condiments made with locally grown ingredients. Performers on stilts wander through the crowd interacting with guests, and musical acts take the stage. If hunger hits you, try the funnel cake and French fries for warm and filling indulgences.

Most beer fanatics know Harpoon Brewery for their award-winning brews and the annual festivals held at their Boston location. But they also have a Vermont brewery that hosts the Harpoon BBQ Festival, an annual cook-off that takes place every July. Think: Beer and BBQ...and lots of it. This two day festival is the backdrop for a competitive BBQ tournament that hosts teams from all over the country.

The Annual Holiday House Tour is held annually and takes place during Christmas. Attendees of this charming annual event are greeted at each house by a host who shares the details and history of the residence. Enjoy a reception with the other house tour attendees at the last stop!

Information about vacation rentals in Woodstock

🏡 Vacation rentals available 247 rentals
💳 Possible discounts up to 50%
🌙 Nightly prices starting at $140
⭐ Popular amenities Pets allowed, Fireplace and Pool
🐾 Pet friendly homes 26 homes
🏊 Vacation rentals with pools 92 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Woodstock?

The price of a night's stay in Woodstock starts at $140. If you’re interested in a bed and breakfast rental, the average price is $340 per night. A house rental Woodstock will cost on average $760 per night.

How many vacation rentals are available to book in Woodstock?

Currently there are 247 rentals in Woodstock to browse and book for your trip.

What are the most popular amenities for vacation homes in Woodstock?

Travelers look for Pets allowed, Fireplace, and Pool when booking a vacation rental in Woodstock.

How many vacation rentals with pools are there in Woodstock?

Choose from 92 vacation rentals available to book in Woodstock.

Are dogs allowed in vacation homes in Woodstock?

Yes, currently there are 26 vacation homes in Woodstock that allow pets and the average nightly price is $507.

What's the best month to travel to Woodstock?

If you are choosing a vacation rental in Woodstock, keep in mind that rainy season is typically in December or January, with September often being the driest.

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