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Woodstock vacation rentals

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Best Woodstock vacation rentals

Most recommended vacation rentals in Woodstock

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Riverside Cottage - Woodstock - Living room
Riverside Cottage
Woodstock, VT
8.5Very good(18)
Pet friendly
$312+
Check availability
Woodstock Village Carriage House - Woodstock - Building
Woodstock Village Carriage House
Woodstock, VT
$359+
Check availability
Treehouse at Wise Pines- SoBo - Woodstock - Bedroom
Treehouse at Wise Pines- SoBo
Woodstock, VT
$186+
Check availability
Private & Affordable Charming Custom Ranch In S. Woodstock. March Discounts !! - Woodstock - Living room
Private & Affordable Charming Custom Ranch In S. Woodstock. March Discounts !!
Woodstock, VT
Free Wi-Fi
Pet friendly
$580+
Check availability
Delightful Cozy Space in Woodstock Village - Woodstock
Delightful Cozy Space in Woodstock Village
Woodstock, VT
Pet friendly
$328+
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Vermont Gem Near Woodstock and Quechee - Woodstock - Living room
Vermont Gem Near Woodstock and Quechee
Woodstock, VT
Pet friendly
$665+
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Luxury, private, peaceful home with Instagram worthy amenities! - Woodstock - Living room
Luxury, private, peaceful home with Instagram worthy amenities!
Woodstock, VT
Free Wi-Fi
$1,238+
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Scenic South Woodstock, Vermont home - Woodstock - Living room
Scenic South Woodstock, Vermont home
Woodstock, VT
Free Wi-Fi
$703+
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Beautiful 3 bed, 3.5 bath on 6 acres - Woodstock - Living room
Beautiful 3 bed, 3.5 bath on 6 acres
Woodstock, VT
Free Wi-Fi
$611+
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Charming Log Cabin Apartment in Woodstock Village - Woodstock - Dining room
Charming Log Cabin Apartment in Woodstock Village
Woodstock, VT
Free Wi-Fi
$223+
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New Vermont Luxury In Woodstock Village: Private Home, Pond & Mountain Views - Woodstock - Living room
New Vermont Luxury In Woodstock Village: Private Home, Pond & Mountain Views
Woodstock, VT
Free Wi-Fi
$1,101+
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Your Vermont Vacation Awaits! - Woodstock - Living room
Your Vermont Vacation Awaits!
Woodstock, VT
Free Wi-Fi
Pool
$699+
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Relaxing retreat in the mountains 20 min to Killington - Woodstock - Bedroom
Relaxing retreat in the mountains 20 min to Killington
Woodstock, VT
Free Wi-Fi
$394+
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Luxury Estate 25 Gorgeous Acres of Privacy Family GetawaySwimming Pond - Woodstock - Bedroom
Luxury Estate 25 Gorgeous Acres of Privacy Family GetawaySwimming Pond
Woodstock, VT
Pet friendly
Spa
$1,420+
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The Daydream Cottage - Woodstock
The Daydream Cottage
Woodstock, VT
5.0Fair(2)
Pet friendly
$394+
Check availability
Woodstock Four Season Family Estate Has It All Recently Renovated! - Woodstock
Woodstock Four Season Family Estate Has It All Recently Renovated!
Woodstock, VT
Pet friendly
$1,772+
Check availability
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$0 - $899$899 - $1,798$1,798 - $2,697$2,697 - $3,595$3,595+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

April

High season

October

Average price (weeknight)

$610

Average price (weekend night)

$651
Cheapest month to stay with an average 59% drop in price.
Most expensive month to stay with an average 73% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Woodstock vacation rental deals

  • Vacation rentals in Woodstock are around 78% more expensive than hotels on average. Search here to compare prices for all accommodation types in Woodstock.
  • The best vacation rental properties in Woodstock are Scenic South Woodstock, Vermont home (10.0, 26 reviews), Classic, cozy farmhouse in the 4 season playground of VT's prettiest town! (10.0, 20), and Perfect Design & Location for the VT Experience. \'Hope Upon, Up Above\' (9.9, 36), based on ratings and reviews from real travelers.
  • The cheapest night for renting a vacation home in Woodstock is Saturday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Woodstock for 3 days.
See more tips

FAQs when booking a vacation home in Woodstock

  • What types of vacation rentals are available in Woodstock?

    There are loads of different property types that you can make your vacation home in Woodstock. You’ll find agritourism, apartments, cabins, chalets, condos, cottages and houses.

  • Are there any pet-friendly vacation rentals in Woodstock?

    There are a number of dog and pet-friendly Woodstock vacation rentals, with around 17% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Woodstock?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Woodstock?

Our map will help you find the perfect place to stay in Woodstock by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Woodstock

Woodstock vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Woodstock. Find cheap vacation homes to rent in Woodstock. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Woodstock that suits you best.

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