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Woodstock Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Bed & Breakfast
House
Pension
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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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Save up to 58%

Best Vacation Home Deals in Woodstock

House Woodstock
Apr 8 - Apr 15
-20%
$325
$260 per night
House ∙ 10 guests ∙ 4 bedrooms
Wonderful Vacation Home in Woodstock with Large Whirlpool + Mountain View
5.0
"Excellent" (132 ratings)
Woodstock, Windsor County, Vermont, United States
Details
Vrbo
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Farmhouse Woodstock
Apr 8 - Apr 15
-58%
$453
$191 per night
Farmhouse ∙ 8 guests ∙ 4 bedrooms
Farm in Woodstock with Yard + Vineyard Views
5.0
"Excellent" (20 ratings)
Woodstock, Windsor County, Vermont, United States
Details
Vrbo
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House Woodstock
Apr 22 - Apr 29
-51%
$454
$222 per night
House ∙ 4 guests ∙ 2 bedrooms
Beautiful House in Woodstock with Grill & Yard + Beautiful Views
5.0
"Excellent" (37 ratings)
Woodstock, Windsor County, Vermont, United States
Details
Vrbo
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Find a rental meeting your expectations among the 285 great vacation rentals from numerous partner websites in Woodstock. HomeToGo immediately compares all of these properties so you can save up to 32%!

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Top-Rated Rentals and Accommodations in Woodstock

House Woodstock
Aug 26 - Sep 2
$300 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Woodstock with Grill & Yard
5.0
"Excellent" (91 ratings)
Woodstock, Windsor County, Vermont, United States
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Apartment Woodstock
May 20 - May 27
$234 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Village Of Woodstock with Grill & Yard
5.0
"Excellent" (56 ratings)
Woodstock, Windsor County, Vermont, United States
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Cottage Woodstock
Apr 29 - May 6
$176 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Woodstock with Yard & Grill + Gorgeous Views
5.0
"Excellent" (43 ratings)
Woodstock, Windsor County, Vermont, United States
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Recommended Vacation Rentals in Woodstock

Find your perfect vacation rental in Woodstock: from $155 per night

House Woodstock
Jan 6 - Jan 13
$321 per night
House ∙ 6 guests ∙ 4 bedrooms
Beautiful House in Woodstock with Grill & Yard
5.0
"Excellent" (57 ratings)
Woodstock, Windsor County, Vermont, United States
Details
Vrbo
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House Woodstock
Nov 25 - Dec 2
$360 per night
House ∙ 7 guests ∙ 3 bedrooms
Whole Vacation Home in Woodstock with Yard, Grill & Pool
5.0
"Excellent" (35 ratings)
Woodstock, Windsor County, Vermont, United States
Details
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Apartment Woodstock
Apr 1 - Apr 8
-31%
$228
$161 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Rental Apartment in Village Of Woodstock with Yard
4.9
"Excellent" (96 ratings)
Woodstock, Windsor County, Vermont, United States
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Cottage Woodstock
Jun 17 - Jun 24
$238 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Village Of Woodstock with Grill & Yard
4.8
"Excellent" (84 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Jul 1 - Jul 8
$376 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in South Woodstock with Outdoor Fireplace
4.9
"Excellent" (216 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
May 6 - May 13
-24%
$850
$651 per night
House ∙ 10 guests ∙ 5 bedrooms
Wonderful Vacation Home in Woodstock with Yard & Grill
5.0
"Excellent" (25 ratings)
Woodstock, Windsor County, Vermont, United States
Details
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House Woodstock
Apr 1 - Apr 8
-32%
$1,198
$1,171 per night
House ∙ 4 guests ∙ 6 bedrooms
House in Woodstock with Spacious Parking
4.9
"Excellent" (25 ratings)
Woodstock, Windsor County, Vermont, United States
Details
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Bed & Breakfast Woodstock
Jan 20 - Jan 27
-49%
$453
$230 per night
Bed & Breakfast ∙ 4 guests ∙ 1 bedroom
Wonderful Bed And Breakfast in Village Of Woodstock with Pool, Patio & Yard
4.9
"Excellent" (144 ratings)
Woodstock, Windsor County, Vermont, United States
Details
Expedia
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Motel Woodstock
May 6 - May 13
-35%
$288
$188 per night
Motel ∙ 4 guests ∙ 1 bedroom
Motel in Woodstock
4.7
"Outstanding" (228 ratings)
Woodstock, Windsor County, Vermont, United States
Details
Expedia
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Budget-friendly Vacation Rentals in Woodstock

Apartment Woodstock
Nov 25 - Dec 2
-19%
$237
$192 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Village Of Woodstock with Grill
5.0
"Excellent" (56 ratings)
Woodstock, Windsor County, Vermont, United States
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Chalet Woodstock
Dec 9 - Dec 16
$259 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Modern Chalet in Woodstock with Finnish Sauna
5.0
"Excellent" (56 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Mar 23 - Mar 30
$289 per night
House ∙ 6 guests ∙ 3 bedrooms
Entire Vacation Home in Woodstock with Private Patio
5.0
"Excellent" (74 ratings)
Woodstock, Windsor County, Vermont, United States
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Vacation Houses With Pools

Make a splash on your next vacation! Over 33% of in Woodstock vacation rentals have a swimming pool.

Chalet Pool Woodstock
Mar 9 - Mar 16
$258 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Modern Chalet in Woodstock with Finnish Sauna
5.0
"Excellent" (56 ratings)
Woodstock, Windsor County, Vermont, United States
Pool
Details
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House Pool Woodstock
Nov 25 - Dec 2
$360 per night
House ∙ 7 guests ∙ 3 bedrooms
Whole Vacation Home in Woodstock with Yard, Grill & Pool
5.0
"Excellent" (35 ratings)
Woodstock, Windsor County, Vermont, United States
Pool
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House Pool Woodstock
Apr 22 - Apr 29
$950 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Village Of Woodstock with Yard, Pool & Grill + Expansive Views
4.6
"Outstanding" (21 ratings)
Woodstock, Windsor County, Vermont, United States
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Woodstock!

Apartment Pet-friendly Woodstock
May 20 - May 27
$234 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Village Of Woodstock with Grill & Yard
5.0
"Excellent" (56 ratings)
Woodstock, Windsor County, Vermont, United States
Pet-friendly
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Apartment Pet-friendly Woodstock
Nov 25 - Dec 2
-19%
$236
$192 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Village Of Woodstock with Grill
5.0
"Excellent" (56 ratings)
Woodstock, Windsor County, Vermont, United States
Pet-friendly
Details
Vrbo
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House Pet-friendly Woodstock
Apr 22 - Apr 29
-51%
$450
$220 per night
House ∙ 4 guests ∙ 2 bedrooms
Beautiful House in Woodstock with Grill & Yard + Beautiful Views
5.0
"Excellent" (37 ratings)
Woodstock, Windsor County, Vermont, United States
Pet-friendly
Details
Vrbo
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Woodstock with their own private patios and balconies.

House Balcony Woodstock
Apr 1 - Apr 8
-32%
$1,185
$806 per night
House ∙ 4 guests ∙ 6 bedrooms
House in Woodstock with Spacious Parking
4.9
"Excellent" (25 ratings)
Woodstock, Windsor County, Vermont, United States
Balcony
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Villa Balcony Woodstock
Mar 25 - Apr 1
$4,149 per night
Villa ∙ 46 guests ∙ 15 bedrooms
Villa in Woodstock with Patio
4.2
"Very good" (5 ratings)
Woodstock, Windsor County, Vermont, United States
Balcony
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House Balcony Woodstock
Apr 22 - Apr 29
$2,900 per night
House ∙ 14 guests ∙ 7 bedrooms
Vacation Home in Woodstock with Grill & Yard
5.0
"Excellent" (12 ratings)
Woodstock, Windsor County, Vermont, United States
Balcony
Details
Vrbo
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Popular Rental Amenities in Woodstock

  • Internet (261)
  • Air conditioning (241)
  • TV (227)
  • Yard (226)
  • No smoking (170)
  • No pets (151)
  • Balcony/Patio (150)
  • Fireplace (124)
  • Pool (89)
  • Microwave (86)
  • Fishing (79)
  • Kitchen (62)

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 need internet access during your vacation or you never miss an episode of your favorite show, as the most frequently offered amenities are "Internet" and "Air conditioning." It is also possible to find a property in Woodstock if you want a rental with a jacuzzi as 30 of the listed accommodations there provide "Hot tub."

The Weather in Woodstock

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32°
12°
17 days 17
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34°
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14 days 14
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43°
21°
16 days 16
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32°
12 days 12
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72°
46°
15 days 15
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54°
14 days 14
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84°
59°
13 days 13
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82°
57°
10 days 10
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75°
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9 days 9
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63°
41°
15 days 15
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46°
28°
11 days 11
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37°
23°
19 days 19
Jan.
Feb.
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Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
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- Rainy days

7-Day Weather Forecast in Woodstock

Tue, 21 Mar
41°
26°

15%

5 h

5 mi/h

Wed, 22 Mar
44°
30°

15%

0 h

2 mi/h

Thu, 23 Mar
44°
33°

15%

1 h

6 mi/h

Fri, 24 Mar
33°
32°

15%

0 h

2 mi/h

Sat, 25 Mar
32°
32°

15%

0 h

5 mi/h

Sun, 26 Mar
35°
30°

15%

1 h

10 mi/h

Mon, 27 Mar
37°
28°

15%

1 h

4 mi/h

Accommodations for your vacation in Woodstock

In Woodstock, bed & breakfast are the most common type of accommodation. Additionally, these accommodations have an average size of 31 m² as well as a median price of $351 a night. Furthermore, these rentals are perfect if you're going in a group of 3, it represents the average number of guests bed & breakfast 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 33 offers to compare. These accommodations cost $861 a night on average and have an average size of 222 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 284 properties
💳 Possible discounts up to 52%
🌙 Nightly prices starting at $155
⭐ Popular amenities Internet, Air conditioning and TV
🐾 Pet friendly accommodations 23 properties
🏊 Vacation rentals with pools 99 properties

Frequently Asked Questions

What is the typical nightly price for a vacation home in Woodstock?

The average accommodation in Woodstock is priced at $155 per night. If you would like to stay in a bed & breakfast, the average price is $351 per night. A house rental Woodstock will cost on average $861 per night.

How many vacation homes are available to book in Woodstock?

Currently there are 284 vacation homes from 5 different providers in Woodstock.

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

Three most popular amenities for vacation home rentals in Woodstock include accommodations that have: Air conditioning, Internet, and TV.

How many vacation rentals with pools are there in Woodstock?

Check out 99 vacation rentals available in Woodstock for renting.

Are dogs allowed in vacation homes in Woodstock?

Sure, currently there are 23 vacation rentals in Woodstock that allow pets and the average nightly rate is $645.

When is it better to travel to Woodstock?

Woodstock has its warmest time of year in July and August, with average nightly prices around $155.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Woodstock TripAdvisor Vacation Rentals in Woodstock Vrbo Vacation Rentals in Woodstock VacationRentals.com Vacation Rentals in Woodstock HouseTrip Vacation Rentals in Woodstock FlipKey Vacation Rentals in Woodstock Homestay.com Vacation Rentals in Woodstock Only-apartments Vacation Rentals in Woodstock Interhome Vacation Rentals in Woodstock Novasol Vacation Rentals in Woodstock HomeEscape Vacation Rentals in Woodstock

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