Woodstock Vacation Rentals

Compare 1,681 available properties from 18 providers
Woodstock
Anytime
2 guests
Save up to 22%

Best Vacation Home Deals in Woodstock

-15%
e.g. 3/23 - 3/30
Apartment ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $170 $202
VRBO
5.0
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-17%
e.g. 4/1 - 4/8
Apartment ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $116 $140
VRBO
5.0
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-22%
e.g. 7/6 - 7/13
House ∙ 6 guests ∙ 3 bedrooms
Woodstock, Windsor County, Vermont, United States
from $277 $355
VRBO
5.0
View deal

Find a rental meeting your expectations among the 1,681 great vacation rentals from numerous partner websites in Woodstock. HomeToGo immediately compares all of these properties so you can save up to 22%!

Recommended Vacation Rentals in Woodstock

Find your perfect vacation rental in Woodstock: from $35 per night

Apartment ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $116
VRBO
5.0
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $187
VRBO
5.0
View deal
Apartment ∙ 2 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $139
VRBO
4.2
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House ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $125
VRBO
4.9
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House ∙ 6 guests ∙ 2 bedrooms
Woodstock, Windsor County, Vermont, United States
from $281
VRBO
4.9
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $289
VRBO
4.9
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $163
VRBO
4.9
View deal
House ∙ 7 guests ∙ 3 bedrooms
Woodstock, Windsor County, Vermont, United States
from $82
VRBO
5.0
View deal
-15%
Resort ∙ 4 guests
Woodstock, Windsor County, Vermont, United States
from $269 $318
Expedia.com
4.5
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 4 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $175
VRBO
5.0
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Fireplace
House ∙ 10 guests ∙ 5 bedrooms
Woodstock, Windsor County, Vermont, United States
from $701
Airbnb
5.0
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Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Woodstock, Windsor County, Vermont, United States
from $145
Airbnb
4.5
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 8 guests ∙ 3 bedrooms
Woodstock, Windsor County, Vermont, United States
from $310
VRBO
4.8
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Pet-friendly
House ∙ 8 guests ∙ 4 bedrooms
Woodstock, Windsor County, Vermont, United States
from $343
VRBO
5.0
View deal
Pet-friendly
House ∙ 8 guests ∙ 4 bedrooms
Woodstock, Windsor County, Vermont, United States
from $426
Airbnb
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 6 guests ∙ 3 bedrooms
Woodstock, Windsor County, Vermont, United States
from $333
VRBO
5.0
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Fishing
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Woodstock, Windsor County, Vermont, United States
from $312
Booking.com
4.4
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Fishing
Private room ∙ 2 guests
Woodstock, Windsor County, Vermont, United States
from $175
Booking.com
4.9
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Popular Rental Amenities in Woodstock

  • Internet (144)
  • TV (125)
  • Kitchen (108)
  • Washer (95)
  • AC (84)
  • Fireplace (78)
  • Parking (62)
  • Yard (62)
  • Microwave (61)
  • No smoking (61)
  • Dishwasher (60)
  • Grill (51)
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 want to tune out with some TV time or you need internet access during your vacation, as the most frequently offered amenities are "TVs" and "internet." It is also possible to find a property in Woodstock if you want a rental with a sauna as 210 of the listed accommodations there provide "saunas."

The Weather in Woodstock

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12°
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12°
43°
21°
57°
32°
72°
46°
77°
54°
84°
59°
82°
57°
75°
50°
63°
41°
46°
28°
37°
23°
Jan.
Feb.
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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.

Accommodations in Woodstock

In Woodstock, house rentals are the most common type of accommodation. Additionally, these accommodations have an average size of 2,470 ft² as well as a median price of $442 a night. Furthermore, these rentals are perfect if you're going in a group of 8, it represents the average number of guests house rentals can welcome in Woodstock. You can also search and find other accommodation options in Woodstock. Apartment rentals are, for example, another popular property type in this destination, with 28 offers to compare. These accommodations cost $249 a night on average and have an average size of 1,200 ft².

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.

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Food & Drinks

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.

Family Activities

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.

Local Attractions

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.

Local Events

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!

We compare more than 600 providers, including:

Booking.com Vacation Rentals in Woodstock VRBO Vacation Rentals in Woodstock HomeAway Vacation Rentals in Woodstock Airbnb Vacation Rentals in Woodstock TripAdvisor Vacation Rentals in Woodstock VacationRentals.com Vacation Rentals in Woodstock HouseTrip Vacation Rentals in Woodstock FlipKey Vacation Rentals in Woodstock 9flats.com Vacation Rentals in Woodstock VaycayHero Vacation Rentals in Woodstock PerfectPlaces.com Vacation Rentals in Woodstock Homestay.com Vacation Rentals in Woodstock Only-apartments Vacation Rentals in Woodstock Interhome Vacation Rentals in Woodstock Bedycasa Vacation Rentals in Woodstock Novasol Vacation Rentals in Woodstock HomeEscape Vacation Rentals in Woodstock

Things to See and Do in Woodstock

Vacation Destinations Near Woodstock