Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

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New Stunning Light-filled Woodstock Home w/Hot Tub
Entire residential home · 2 guests · 1 bed · 1 bath
New Stunning Light-filled Woodstock Home w/Hot TubBrand new listing! As featured in Hudson Valley Style Magazine. Explore Woodstock and nearby mountains from this light-filled 1700 sq ft 1-BR home. This house has over a half acre all to itself, merely a brisk 15 minute walk into the center of Woodstock - no car needed! Features: - Private patio w/fire pit, grill & hot tub. - 65-inch 4K TV w/soundbar - 2 desks - 150mbps Wi-Fi, routers on both floors - Queen bed Note that it has a shared driveway with the owner, who lives up the hill.
Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace
PLUS
Entire guesthouse · 2 guests · 1 bed · 1 bath
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 bath
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.

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Popular amenities for Woodstock vacation rentals

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

Other great vacation rentals in Woodstock

SUPERHOST
  1. Entire villa
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The Falls
$80 per night
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Work & Play in Woodstock! In town~WiFi~Hot Tub
$342 per night
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Brook Cottage Too: 5-star pristine/luxury SHELTER
$250 per night
  1. Entire residential home
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Mid-Century Modern Sanctuary Minutes to Woodstock
$625 per night
SUPERHOST
  1. Entire guest suite
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Peace & Quiet in Woodstock w/ room to spread out!
$97 per night
PLUS
  1. Entire guesthouse
  2. Bearsville
Mt. Guardian Guest House Exquisite Mountain Views
$195 per night
SUPERHOST
  1. Entire bungalow
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Woodstock Charmer
$161 per night
SUPERHOST
  1. Entire guesthouse
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Steps To Town /Bus /Pets Ok. No Xtra Fees 5 STAR!
$198 per night
SUPERHOST
  1. Entire cottage
  2. Woodstock
Stunning Woodstock 1 BR Hideaway
$225 per night
SUPERHOST
  1. Entire cottage
  2. Woodstock
Cozy Woodstock cottage
$123 per night
SUPERHOST
  1. Entire cabin
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Byrdcliffe Artist Studio
$180 per night
SUPERHOST
  1. Entire cottage
  2. Woodstock
Streamside Cottage walk to Town
$177 per night

Your guide to Woodstock

Welcome to Woodstock


How do I get around Woodstock?

If you’re looking to fly in, the New York Stewart International Airport (SWF) in New Windsor is a 50-minute drive from the south, while Albany International Airport (ALB) is about an hour north. However it may be easier to find a flight to one of the three major New York City airports ― Newark Liberty International Airport (EWR), LaGuardia Airport (LGA), and John F. Kennedy International Airport (JFK) ― each about a two-hour drive away. Bus service is available from Manhattan directly to Woodstock, while trains run to Poughkeepsie, about 45 minutes away. A rental car is the most convenient option to travel around the Catskills region.


When is the best time to stay in a vacation rental in Woodstock?

Woodstock is at its best in the summer months with comfortable temperatures from day to night, though a burst of summer rain isn’t unusual. Events are also in full swing, such as the Maverick Festival, with chamber music from June to September; Mower’s Saturday Market flea market and the Woodstock Farm Festival from May through the fall; and the Woodstock-New Paltz Arts & Craft Show, with a spring edition in May and fall one in September. Summer is also prime time to revel in the greenery with outdoor activities such as hiking and biking. Autumn brings its own delights with stunning fall colors, especially around the second week of October. While snow tends to blanket the area in the coldest months, the Catskills’ winter sports offerings can’t be topped. As the snow melts away, spring brings back the tourists, as the temperature works its way up to its comfy zone.


What are the top things to do in Woodstock?

Overlook Mountain Wild Forest

While most mountain hikes lure visitors with their sprawling mountaintop views, Overlook Mountain (with the Hudson River Valley in the foreground and five states in the distance) does that and so much more. Along the way up the Spur Trail, you’ll find the ruins of the never-finished Overlook Mountain House. At the summit, an impressive fire tower reaches 3,140 feet high. Also worth a visit: The Karma Triyana Dharmachakra Tibetan Buddhist monastery across the street from the trailhead.

The Center for Photography at Woodstock

What started as an artists’ colony’s urge to give photographers their own space has grown into a gallery and workshop center that both showcases and supports photography in every kind of light.

Opus 40

Just a 10-minute drive to the east in Saugerties is a 6.5-acre earthwork sculpture that was hand-shaped from bluestone by artist Harvey Fite over the course of 37 years. Sitting on 50 acres of meadows, forest, and quarries, the site — often likened to Stonehenge — also hosts theatrical and musical performances.