Vacation rentals in Woodstock - HomeToGo base64Hash Vacation rentals in Woodstock - HomeToGo

Vacation rentals in Woodstock

Find 269 available vacation homes
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Top 15 Recommended vacation rentals in Woodstock

Find your perfect vacation rental in Woodstock from just $178 per night!

House Woodstock
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with BBQ & terrace | Perfect for remote work

Woodstock, Windsor County, Vermont, United States
from $212
per night
from $212
per night
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Apartment Woodstock
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental apartment with barbeque, sauna & garden

Woodstock, Windsor County, Vermont, United States
from $596
per night
Outstanding(2 ratings)
from $596
per night
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House Woodstock
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with jacuzzi, yard & BBQ | Mountain view | Pet-friendly

Woodstock, Windsor County, Vermont, United States
from $1,148
per night
Outstanding(22 ratings)
from $1,148
per night
View deal
Cabin Woodstock
Cabin ∙ 4 guests ∙ 3 bedrooms

Family-oriented cottage with grill & garden | Good for workation

Woodstock, Windsor County, Vermont, United States
from $495
per night
from $495
per night
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Apartment Woodstock
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment with terrace & BBQ | Nature view

Woodstock, Windsor County, Vermont, United States
from $201
per night
Outstanding(64 ratings)
from $201
per night
View deal
Cabin Woodstock
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with barbecue & garden

Woodstock, Windsor County, Vermont, United States
from $178
per night
Outstanding(116 ratings)
from $178
per night
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House Woodstock
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbeque & terrace

Woodstock, Windsor County, Vermont, United States
from $640
per night
from $640
per night
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House Woodstock
House ∙ 6 guests ∙ 4 bedrooms

Child-friendly beautiful house with barbecue, yard & terrace | Nature view | Suitable for remote work

Woodstock, Windsor County, Vermont, United States
from $348
per night
Outstanding(93 ratings)
from $348
per night
View deal
House Woodstock
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with terrace & grill

Woodstock, Windsor County, Vermont, United States
from $590
per night
Outstanding(59 ratings)
from $590
per night
View deal
House Woodstock
House ∙ 8 guests ∙ 4 bedrooms

House with BBQ & terrace | Mountain view

Woodstock, Windsor County, Vermont, United States
from $394
per night
Outstanding(20 ratings)
from $394
per night
View deal
Chalet Woodstock
Chalet ∙ 6 guests ∙ 2 bedrooms

Chalet with barbeque, pool & yard

Woodstock, Windsor County, Vermont, United States
from $243
per night
Outstanding(78 ratings)
from $243
per night
View deal
House Woodstock
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with yard, barbeque & patio | Mountain view

Woodstock, Windsor County, Vermont, United States
from $863
per night
Outstanding(23 ratings)
from $863
per night
View deal
House Woodstock
House ∙ 4 guests ∙ 5 bedrooms

Fully equipped wonderful vacation home with BBQ, sauna & yard

Woodstock, Windsor County, Vermont, United States
from $856
per night
Outstanding(37 ratings)
from $856
per night
View deal
Apartment Woodstock
Apartment ∙ 4 guests ∙ 1 bedroom

Rental apartment with yard, terrace & grill

Woodstock, Windsor County, Vermont, United States
from $199
per night
Outstanding(76 ratings)
from $199
per night
View deal
House Woodstock
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with BBQ, jacuzzi & pool

Woodstock, Windsor County, Vermont, United States
from $232
per night
from $232
per night
View deal

Vacation Rentals With Fireplaces

Condo  Woodstock
from $194
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped nice condo with yard & patio | Nature view | Good for workation | Pets allowed

Woodstock, Windsor County, Vermont, United States
Fireplace
View deal
House  Woodstock
from $142
per night
House ∙ 4 guests ∙ 1 bedroom

Family-oriented wonderful house | Dogs allowed

Woodstock, Windsor County, Vermont, United States
Fireplace
View deal
House  Woodstock
from $141
per night
House ∙ 4 guests ∙ 1 bedroom

Vacation home with 1 room for 4 persons

Woodstock, Windsor County, Vermont, United States
Fireplace
View deal
See all offers

Vacation rentals and apartments with air conditioning

House  Woodstock
from $290
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with patio & garden | Pets are welcome

Woodstock, Windsor County, Vermont, United States
Air conditioning
View deal
House  Woodstock
from $520
per night
House ∙ 8 guests ∙ 4 bedrooms

Lovely vacation home with 4 rooms for 8 persons

Woodstock, Windsor County, Vermont, United States
Air conditioning
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House  Woodstock
from $268
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with 2 rooms for 4 persons

Woodstock, Windsor County, Vermont, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House  Woodstock
from $1,774
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with grill

Woodstock, Windsor County, Vermont, United States
Balcony
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House  Woodstock
from $155
per night
House ∙ 2 guests ∙ 1 bedroom

House with 1 room for 2 persons

Woodstock, Windsor County, Vermont, United States
Balcony
View deal
House  Woodstock
from $2,850
per night
House ∙ 14 guests ∙ 7 bedrooms

Vacation home with yard, BBQ & patio | Nature view | Good for workation

5.0
Outstanding(14 ratings)
Woodstock, Windsor County, Vermont, United States
Balcony
View deal
See all offers

Budget-friendly Vacation Rentals in Woodstock

Find Fantastic yet Inexpensive Offers

Resort Woodstock
from $305
per night
Resort ∙ 4 guests ∙ 1 bedroom

Resort with patio & yard

Woodstock, Windsor County, Vermont, United States
View deal
Bed and breakfast Woodstock
from $193
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast for 2 persons

4.9
Outstanding
Woodstock, Windsor County, Vermont, United States
View deal
House Woodstock
from $1,912
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbecue, private pool & yard | Mountain view

Woodstock, Windsor County, Vermont, United States
View deal

Top-Rated Rentals and Accommodations in Woodstock

Book Vacation Rental Offers with the Highest User Rating

Bed and breakfast Woodstock
from $385
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with jacuzzi & garden | Garden view | Perfect for remote work

5.0
Outstanding(25 ratings)
Woodstock, Windsor County, Vermont, United States
View deal
Bed and breakfast Woodstock
from $367
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented B&B with fast internet & jacuzzi

4.8
Outstanding(14 ratings)
Woodstock, Windsor County, Vermont, United States
View deal
Resort Woodstock
from $550
per night
Resort ∙ 4 guests ∙ 1 bedroom

Pleasant resort with pool, terrace & garden

4.6
Excellent(501 ratings)
Woodstock, Windsor County, Vermont, United States
View deal

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Popular Rental Amenities in Woodstock

  • Pet-friendly (97)
  • Fireplace (182)
  • Pool (95)
  • TV (253)
  • WiFi (309)
  • Fishing (149)
  • Kitchen (143)
  • Air conditioning (310)
  • Washing machine (64)
  • Hot tub (22)
  • No smoking (321)
  • Parking (34)

Finding an accommodation with a pool shouldn't be too hard in Woodstock. One-third of the accommodations include pools. Hotel room with pools in Woodstock are a wonderful choice for groups of 3 and cost, on average, $658 a night. nearly all of Woodstock's rentals offering a pool are situated within two miles of water, divide your time between the pool and the waterfront

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.

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.

Information about vacation rentals in Woodstock

🏡 Vacation rentals available 269 rentals
💳 Possible discounts up to 12%
🌙 Nightly prices starting at $178
⭐ Popular amenities Pets allowed, Fireplace and Pool
🐾 Pet friendly homes 60 homes
🏊 Vacation rentals with pools 94 homes

Frequently Asked Questions

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

The price of a night's stay in Woodstock starts at $178. $904 is the average nightly price for house rentals in Woodstock. Bed and breakfast rentals in Woodstock cost $428 per night on average.

How many vacation homes are available to book in Woodstock?

There are currently 269 rentals in Woodstock to browse and rent for your upcoming trip.

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

If you're looking to book a vacation rental in Woodstock, others search for accommodation with these amenities: Pets allowed, Fireplace and Pool.

How many vacation homes with a pool are in Woodstock?

Choose from 94 vacation rentals available to book in Woodstock.

Are pets allowed in vacation rentals in Woodstock?

If you are traveling with a pet in Woodstock - 22% of vacation homes are pet-friendly.

What's the best time of year to travel to Woodstock?

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

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