Skip to content

Holiday rentals in Woodstock

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace
PLUS
Entire guest house · 2 guests · 1 bed · 1 bathroom
Pick Herbs at a Quirky Stone Cottage with BBQ and FireplaceSnuggle up on a leather sofa by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical, compact home has a private deck with a bbq, a garden with a hammock and a fire pit. There is a full size Murphy bed and a sofa (not a pull-out). Full kitchen except for an oven.
Dutch Touch Woodstock Cottage
SUPERHOST
Entire residential home · 2 guests · 1 bed · 1 bathroom
Dutch Touch Woodstock CottageThe Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.
Rocket Room - Rock Stars Only
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom
Rocket Room - Rock Stars OnlyWalk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. What are you waiting for?

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Woodstock holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Woodstock

PLUS
  1. Entire guest house
  2. Bearsville
Mt. Guardian Guest House Exquisite Mountain Views
SUPERHOST
  1. Entire cabin
  2. Woodstock
Byrdcliffe Artist Studio
  1. Entire cabin
  2. Woodstock
Brand New Modern Cabin walk to town
  1. Entire residential home
  2. Saugerties
Spacious home in Saugerties/Woodstock
SUPERHOST
  1. Entire residential home
  2. Woodstock
Mountain house with hot tub, in the woods
  1. Entire residential home
  2. Woodstock
New Stunning Light-filled Woodstock Home w/Hot Tub
SUPERHOST
  1. Entire cottage
  2. Woodstock
Gorgeous Private Modern Cottage, Tranquil & Clean
SUPERHOST
  1. Entire cabin
  2. Woodstock
Fast Wifi w/ Desks, Fireplace + Backyard Brook
SUPERHOST
  1. Entire rental unit
  2. Woodstock
Chic Country Apt in Woodstock, NY
SUPERHOST
  1. Entire residential home
  2. Saugerties
Secluded Contemporary Art filled home in the woods
PLUS
  1. Entire cabin
  2. Woodstock
Visit Woodstock from a Radiant 1940s Cottage
SUPERHOST
  1. Entire villa
  2. Woodstock
The Falls