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Woodstock vacation rentals

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Top-rated vacation rentals in Woodstock

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

Cottage in Woodstock
Secluded Farmhouse Style, Close to All
Cozy & charming on a quiet, wooded road with fireplace, gourmet kitchen, spacious dining area, cozy bedroom, living room with modern amenities air conditioning and washer/dryer. Separate yoga/meditation studio (for warmer months) Enjoy the private deck area to grill or relax outside. You’ll feel as if you're in an oasis! And the town of Woodstock is a five minute drive away. Sunfrost farms, a grocery/cafe is a 15 minute walk. Note: We love animals but due to allergies we can't accept any pets.
$191 per night
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Cabin in Woodstock
Brand New Modern Cabin walk to town
This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroom with all new fixtures and a soaking tub. You can walk to town in approximately 10-12 minutes. This is in a neighborhood so there are visible neighbors but the architect utilized the natural surroundings to make it feel like you are in the woods. The beauty of this house is it’s access to town. If you look at my past reviews it’s the same location but a new house in front.
$210 per night
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Rental unit in Woodstock
Hotel Woodstock - Iris Suite
Overlooking the Woodstock village center, this antique hotel has 148 years of history and charm. From the front steps you will feel the same energy that travelers have felt since President Ulysses S. Grant visited Woodstock in 1872. This room 2C is a 1 bedroom apartment with a balcony that overlooks the back of the property. There is a full kitchen and a private bath. You do not need a car! The Trailways bus from NYC stops directly across the green, and walk to everything in the village.
$59 per night
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Stay near Woodstock's top sights

Photo of SILVIA
SILVIA275 locals recommend
Photo of Bread Alone Bakery
Bread Alone Bakery206 locals recommend
Photo of Oriole 9
Oriole 9173 locals recommend
Photo of Garden Cafe Woodstock
Garden Cafe Woodstock234 locals recommend
Photo of Cucina
Cucina298 locals recommend
Photo of Catskill Mountain Pizza Co
Catskill Mountain Pizza Co106 locals recommend

Woodstock summer vacation rentals

Home in Woodstock
Ophelia - Classic Woodstock Artist House
$171 per night
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Home in Woodstock
New Stunning Light-filled Woodstock Home w/Hot Tub
$263 per night
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Rental unit in Woodstock
Hotel Woodstock - Aster Suite
$59 per night
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Rental unit in Woodstock
Hotel Woodstock - Tiger Lily Suite
$59 per night
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Cottage in Woodstock
Luxury+firepit+stream+walk/town=Brook Cottage Too
$245 per night
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Cottage in Woodstock
Romantic luxury+stream+walk to town=Brook Cottage
$295 per night
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Cabin in Woodstock
Visit Woodstock from a Radiant 1940s Cottage
$179 per night
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Rental unit in Woodstock
Hotel Woodstock - Sunflower Loft Suite
$59 per night
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Home in Saugerties
Catskill Retreat w/ Hot Tub | Skiing, Hiking, Etc.
$360 per night
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Home in Woodstock
Woodstock Historic Artist Estate - The Carriage House
$156 per night
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Guesthouse in Woodstock
BOHEMIAN RHAPSODY - Be Here Now
$116 per night
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Cottage in Woodstock
Herb Cottage: history•art•woodstove•walk to town!
$195 per night
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Woodstock house rentals

Home in Woodstock
Woodstock Historic Artist Estate- The Museum House
$297 per night
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Home in Woodstock
Woodstock Historic Artist Estate - The Pond House
$488 per night
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Home in West Hurley
New Breathtaking Catskill Retreat with Views and Hot Tub
$249 per night
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Home in Woodstock
Romance+history+luxury+privacy in town=Maple House
$345 per night
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Home in Woodstock
MountainView, HotTub, Sauna, 2 Fireplcs, fire pit
$280 per night
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Private room in Woodstock
The Treetop Bedroom
$92 per night
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Home in Woodstock
Mountain house with hot tub, in the woods
$299 per night
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Home in Phoenicia
Woodland Valley by Summer | Renovated Bungalow
$207 per night
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Private room in Woodstock
Tranquil Suite - Minutes from Woodstock Center
$78 per night
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Home in Woodstock
Dutch Touch Woodstock Cottage
$128 per night
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Home in Woodstock
Romantic+historic artists cottage in private woods
$236 per night
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Home in Woodstock
HUGE KITCHEN, 4 Pvt. Acres, 7 Min. Town, WiFi, AC
$245 per night
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Woodstock cabin rentals

Cabin in Woodstock
Mountaintop log cabin in woods close to town!
$245 per night
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Cabin in Woodstock
Work & Ski~Woodstock~HotTub~Woodstove~Dogs welcome
$275 per night
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Cabin in Woodstock
Restored Farmhouse with Yoga Studio
$221 per night
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Cabin in Bearsville
Cliffside Solar Japanese Teahouse w/ pool & tennis
$136 per night
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Cabin in Woodstock
Byrdcliffe Artist Studio (27.1-1-70)
$190 per night
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Cabin in Phoenicia
Eddy Cabin - Oasis on Stream
$149 per night
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Cabin in Woodstock
The Pike Lane Cabin & Nature Preserve
$129 per night
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Cabin in Woodstock
Cosy Catskills Cabin, minutes to Woodstock Village
$220 per night
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Cabin in Catskill
Restorative Escape in the Woods with Sauna
$206 per night
Cabin in Phoenicia
Cozy Catskills Cottage on the Esopus Creek
$195 per night
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Cabin in Bearsville
1970s Creekside Cabin | 2 miles from Woodstock
$774 per night
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Cabin in Kingston
Charming cabin in the Catskills! On 11 acres. WIFI
$116 per night
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Your guide to Woodstock

Welcome to Woodstock

Despite the fact that the 1969 Woodstock Festival took place a 90-minute drive to the southwest at Bethel Woods Center for the Arts, the town of Woodstock is the exact cross-section of arts and nature that you’d expect from its association with the famous music fest. Sitting in the foothills of the Catskills, the arts colony was established here in 1902, drawing artists of all types — ranging from craftspeople and photographers to actors and musicians. Free-spirited creativity has a certain kind of purity here, inspired by the vast forests, peaks, and waters — in fact, the Ashokan Reservoir is so crisp that it supplies 40 percent of New York City’s drinking water.


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 book one of the area’s house rentals and 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.

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