Woodstock, VT Vacation Rentals

Our Favorite Vacation Rentals in Woodstock

  • Villa with Pool + Fitness Center Access! | Awesome Location Near the Trails
     3br Villa
    RedAwning
    From
    $370
  • The Farmhouse
    Excellent2br Farmhouse
    HolidayLettings
    From
    $372
  • Villa Near Biking and Hiking Trails | Pool, Restaurant + Fitness Center Access!
     3br Villa
    RedAwning
    From
    $359
  • Lovely Condo / Townhouse in the Heart of Quechee
     2br Home/Apartment
    HolidayLettings
    From
    $252
  • Villa with a Fireplace Near the Trails | Pool + Fitness Center Access!
     2br Villa
    RedAwning
    From
    $323
  • Hakuna Matata
    Nice3br Home/Apartment
    HolidayLettings
    From
    $370
  • Vermont Villa Near the Trails | Pool + Fitness Center Access!
     Villa
    RedAwning
    From
    $269
  • NEW! 'Southgate Healing' Apt w/Views by Killington
     Home/Apartment
    HolidayLettings
    From
    $299

Check prices for these upcoming dates

Woodstock Vacation Rentals with a Pool

  • Modern 5 Bedroom / 4.5 bath Home that Sleeps 12
    Good5br Home/Apartment
    Airbnb
    From
    $735
  • Three Snow Village
    Excellent6br Home/Apartment
    Airbnb
    From
    $509
  • New to Air BnB 4 Bedroom/2 Bath Condo Steps Away from Lake Pinneo!
     4br Home/Apartment
    Airbnb
    From
    $454
  • 2 Bedroom Condo in Quechee, VT
    Excellent2br Home/Apartment
    Airbnb
    From
    $209

Woodstock Vacation Rentals with Wi-Fi

  • Prospect Place
    ExcellentHome/Apartment
    Airbnb
    From
    $283
  • Cozy Woodstock Village 2BR Apartment
     2br Home/Apartment
    Airbnb
    From
    $339
  • 3+ acre woodstock farmhouse with brook and pond
     3br Home/Apartment
    Airbnb
    From
    $931
  • The Cottage on Westerdale Road
    Excellent3br Cottage
    Airbnb
    From
    $494

Woodstock Pet-Friendly Vacation Rentals

  • Great Bear Lodge
     5br Home/Apartment
    HolidayLettings
    From
    $585
  • Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $344
  • ★25 ACRE WOODSTOCK ESTATE ★POSTCARD PERFECT★LUXURY
     5br Home/Apartment
    Airbnb
    From
    $787
  • Romantic Woodstock Suite-Private Entrance, Dogs ok
     Home/Apartment
    Airbnb
    From
    $329

Woodstock Travel Guide

Located in the state of Vermont, Woodstock is a poster-worthy New England little town. The colonial style houses are a reminder of the town's history, which is focused in the area known as The Green. Here you´ll find historical buildings such as Norman Williams Public Library.

Things to Do in Woodstock

This town might be small, but it's packed with places to see, fun activities, rich history, and options to relax. The many parks in the area offer activities such as horseback riding, biking, hiking, kayaking and other water sports.

Best Time to Visit Woodstock

The weather in Woodstock is clearly divided into four seasons. Summer is the most popular with visitors. However, foliage season in the fall is pretty spectacular, and winter is a great time to access ski areas like Mount Peg and Mount Tom, and the Suicide Six Ski Area.

Price and Availability in Woodstock

Most expensive
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The cheapest day to stay at a vacation rental in Woodstock tends to be Monday, while the most expensive day tends to be Thursday. Vacation homes in Woodstock tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Woodstock is in February, while the cheapest month is in May. The most popular time to book a vacation rental in Woodstock is in the high season in February. Woodstock has its low season in April, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Woodstock

Rainy days
92 º40
3
82 º23
4
59 º0
4
56 º2
3
56 º-28
4
68 º-10
2
57 º-9
2
73 º17
4
88 º33
1
93 º40
4
98 º45
6
94 º50
4
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Woodstock. The warmest months in Woodstock are June and May, when temperatures reach 98 ˚F. The coolest month is December, when temperatures drop to -28 ˚F. The wettest month in Woodstock is June with 5.93 inches of rain, while the driest month is August with 1.17 inches of rain.

What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly

Vacation Rentals in Woodstock

At AllTheRooms.com we have vacation rentals from all of the leading providers - Airbnb, Bed and Breakfast, Agoda and more. We have 317 vacation rentals, hotels and other places to stay in Woodstock ranging from cheap options to luxury places to stay. When traveling on a budget, the most economical place to stay in Woodstock is available at $60 per night. The average price of a vacation rental is generally $296 per night.

If you need to stay connected during your trip, then you can choose from over 123 accommodations in Woodstock that have WiFi. 22 places to stay include a morning meal. You can keep up with your workout regime by staying at one of 10 accommodations that provide gym facilities. If you are driving to Woodstock, you'll want to pick from 126 places to stay that provide parking.

AllTheRooms has 32 pet-friendly places to stay in Woodstock, so if you're traveling with your cat or dog you won't have any problems.

177 of our rentals in Woodstock have been reviewed by previous guests. They rated 68% as great. You can instantly book any of 83 places to stay right now.

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