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Woodstock Vacation Rentals

Find 241 available offers from 5 partners
Woodstock
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Farmhouse
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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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Best Vacation Home Deals in Woodstock

Save up to 47%

House Woodstock
Apr 6 - Apr 13
-47%
$415
$220 per night
House ∙ 4 guests ∙ 2 bedrooms
Beautiful House in Woodstock with Grill & Yard + Beautiful Views
5.0
Outstanding (49 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Mar 16 - Mar 23
-23%
$310
$238 per night
House ∙ 8 guests ∙ 3 bedrooms
Charming House in Woodstock with Grill & Yard
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Jun 1 - Jun 8
-17%
$420
$350 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Woodstock with Yard & Grill + Great Views
4.9
Outstanding (38 ratings)
Woodstock, Windsor County, Vermont, United States
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Find a rental meeting your expectations among the 241 great vacation rentals from numerous partner websites in Woodstock. HomeToGo immediately compares all of these properties so you can save up to 47%!

Top-Rated Rentals and Accommodations in Woodstock

Book Vacation Rental Offers with the Highest User Rating

Chalet Woodstock
Aug 11 - Aug 18
$258 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Modern Chalet in Woodstock with Finnish Sauna
5.0
Outstanding (73 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Apr 6 - Apr 13
-17%
$1,172
$977 per night
House ∙ 15 guests ∙ 6 bedrooms
House in Woodstock with Spacious Parking
4.9
Outstanding (25 ratings)
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Nov 11 - Nov 18
-17%
$1,190
$990 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Village Of Woodstock with Yard + Mountain Views
5.0
Outstanding (8 ratings)
Woodstock, Windsor County, Vermont, United States
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Recommended Vacation Rentals in Woodstock

Find your perfect vacation rental in Woodstock: from $177 per night

House Woodstock
Jun 7 - Jun 14
$750 per night
House ∙ 6 guests ∙ 4 bedrooms
House in Woodstock with Grill & Yard + Incredible Views
Woodstock, Windsor County, Vermont, United States
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House Woodstock
Jul 6 - Jul 13
$199 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Woodstock with Yard
5.0
Outstanding (4 ratings)
Woodstock, Windsor County, Vermont, United States
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Motel Woodstock
Nov 11 - Nov 18
$177 per night
Motel ∙ 5 guests ∙ 1 bedroom
Motel in Woodstock
4.7
Excellent (309 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Apr 19 - Apr 26
-37%
$1,114
$705 per night
Resort ∙ 4 guests ∙ 1 bedroom
Resort in Village Of Woodstock with Yard, Pool & Jacuzzi
4.6
Excellent (488 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Mar 30 - Apr 6
-66%
$947
$325 per night
Resort ∙ 4 guests ∙ 1 bedroom
Pleasant Resort in Village Of Woodstock with Pool, Patio & Yard
4.6
Excellent (488 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Apr 19 - Apr 26
-56%
$724
$315 per night
Resort ∙ 4 guests ∙ 1 bedroom
Charming Resort in Village Of Woodstock with Sauna, Hot Tub & Yard
4.6
Excellent (488 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Apr 19 - Apr 26
-56%
$724
$315 per night
Resort ∙ 4 guests ∙ 1 bedroom
Lovely Resort in Village Of Woodstock with Jacuzzi, Pool & Yard + Low-Height View
4.6
Excellent (488 ratings)
Woodstock, Windsor County, Vermont, United States
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Bed and breakfast Woodstock
Mar 30 - Apr 6
-29%
$450
$320 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
B&B in Woodstock with Patio & Yard + Garden Views
5.0
Outstanding (222 ratings)
Woodstock, Windsor County, Vermont, United States
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Resort Woodstock
Apr 19 - Apr 26
-37%
$1,114
$705 per night
Resort ∙ 3 guests ∙ 1 bedroom
Resort in Village Of Woodstock with Sauna, Jacuzzi & Patio
4.6
Excellent (488 ratings)
Woodstock, Windsor County, Vermont, United States
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Budget-friendly Vacation Rentals in Woodstock

Find Fantastic yet Inexpensive Offers

Resort Woodstock
Mar 30 - Apr 6
-53%
$754
$355 per night
Resort ∙ 4 guests ∙ 1 bedroom
Wonderful Resort in Village Of Woodstock with Pool, Jacuzzi & Yard
4.6
Excellent (488 ratings)
Woodstock, Windsor County, Vermont, United States
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Bed and breakfast Woodstock
Sep 21 - Sep 28
$300 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Charming Bed & Breakfast in Woodstock with Grill, Yard & Patio
4.8
Outstanding (94 ratings)
Woodstock, Windsor County, Vermont, United States
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Bed and breakfast Woodstock
Sep 21 - Sep 28
$300 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Wonderful Bed & Breakfast in Woodstock with Pool, Yard & Patio
4.8
Outstanding (94 ratings)
Woodstock, Windsor County, Vermont, United States
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Vacation rentals with Wi-Fi

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

Lodge Woodstock
May 3 - May 10
-19%
$1,291
$1,048 per night
Lodge ∙ 28 guests ∙ 13 bedrooms
Lodge in Killington with Ample Parking + Mountain Views
5.0
Outstanding (61 ratings)
Woodstock, Windsor County, Vermont, United States
Internet
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House Woodstock
Dec 1 - Dec 8
-62%
$464
$177 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Plymouth with Jacuzzi & Grill
5.0
Outstanding
Woodstock, Windsor County, Vermont, United States
Internet
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Chalet Woodstock
Jun 15 - Jun 22
-17%
$533
$442 per night
Chalet ∙ 16 guests ∙ 8 bedrooms
Chalet in Killington with Ample Parking
5.0
Outstanding (137 ratings)
Woodstock, Windsor County, Vermont, United States
Internet
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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.

Bed and breakfast Woodstock
Sep 21 - Sep 28
$315 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Nice B&B in Woodstock with Pool, Yard & Patio + River Views
4.8
Outstanding (94 ratings)
Woodstock, Windsor County, Vermont, United States
Air conditioning
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Bed and breakfast Woodstock
Sep 21 - Sep 28
$315 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
Nice Bed & Breakfast in Woodstock with Pool, Yard & Grill
4.8
Outstanding (94 ratings)
Woodstock, Windsor County, Vermont, United States
Air conditioning
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Bed and breakfast Woodstock
Sep 21 - Sep 28
$300 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
B&B in Woodstock with Pool, Yard & Grill
4.8
Outstanding (94 ratings)
Woodstock, Windsor County, Vermont, United States
Air conditioning
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Vacation homes and rentals with a yard

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Woodstock with private yards.

House Woodstock
Nov 4 - Nov 11
-32%
$1,799
$1,226 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Woodstock with Grill & Yard
5.0
Outstanding (2 ratings)
Woodstock, Windsor County, Vermont, United States
Yard
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House Woodstock
Oct 21 - Oct 28
-68%
$1,800
$568 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Woodstock with Yard & Grill + Natural Views
4.8
Outstanding (22 ratings)
Woodstock, Windsor County, Vermont, United States
Yard
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Bed and breakfast Woodstock
Sep 21 - Sep 28
$315 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Bed & Breakfast in Woodstock with Grill, Pool & Patio
4.8
Outstanding (94 ratings)
Woodstock, Windsor County, Vermont, United States
Yard
Details
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Popular Rental Amenities in Woodstock

  • Pet-friendly (19)
  • Fireplace (113)
  • Pool (81)
  • TV (209)
  • WiFi (232)
  • Fishing (93)
  • Kitchen (54)
  • Air conditioning (225)
  • Washing machine (36)
  • Hot tub (46)
  • No smoking (151)
  • Parking (28)

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 a wheelchair accessible vacation rental as 34 of the listed accommodations there provide "Wheelchair accessible."

The Weather in Woodstock

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32°
12°
17 days 17
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14 days 14
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21°
16 days 16
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32°
12 days 12
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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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57°
10 days 10
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75°
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9 days 9
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63°
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15 days 15
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46°
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11 days 11
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37°
23°
19 days 19
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

7-Day Weather Forecast in Woodstock

Wed, 27 Sep
66°
46°

0%

11 h

2 mi/h

Thu, 28 Sep
68°
48°

10%

11 h

2 mi/h

Fri, 29 Sep
66°
51°

0%

3 h

3 mi/h

Sat, 30 Sep
71°
51°

0%

11 h

1 mi/h

Sun, 1 Oct
68°
50°

0%

11 h

7 mi/h

Mon, 2 Oct
62°
44°

0%

11 h

5 mi/h

Tue, 3 Oct
64°
44°

10%

8 h

2 mi/h

Accommodations for your vacation in Woodstock

In Woodstock, house rental are the most common type of accommodation. Additionally, these accommodations have an average size of 250 m² as well as a median price of $768 a night. Furthermore, these rentals are perfect if you're going in a group of 8, it represents the average number of guests house rental can welcome in Woodstock. You can also search and find other accommodation options in Woodstock. Bed and breakfast rental are, for example, another popular property type in this destination, with 26 offers to compare. These accommodations cost $374 a night on average and have an average size of 30 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 241 homes
💳 Possible discounts up to 47%
🌙 Nightly prices starting at $177
⭐ Popular amenities Pets allowed, Fireplace and Pool
🐾 Pet friendly homes 17 homes
🏊 Vacation rentals with pools 80 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 $177. If you’re interested in a house rental, the average price is $768 per night. A bed and breakfast rental Woodstock will cost on average $374 per night.

How many vacation rentals are available to book in Woodstock?

Currently there are 241 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 80 vacation rentals available to book in Woodstock.

Are dogs allowed in vacation homes in Woodstock?

Yes, currently there are 17 vacation homes in Woodstock that allow pets and the average nightly price is $688.

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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