Find Vacation Rentals in Woodstock, Woodstock

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Popular Woodstock Vacation Rentals

Find the perfect Woodstock vacation rental

Farmhouse Woodstock
$180 per night
Farmhouse ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (23 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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House Woodstock
$750 per night
House ∙ 6 guests ∙ 4 bedrooms
4.9
"Excellent" (24 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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House Woodstock
$297 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (23 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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Cottage Woodstock
$333 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (97 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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House Woodstock
$319 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (7 ratings)
Woodstock, Ulster County, New York, United States
Details
Vrbo
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House Woodstock
$322 per night
House ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (27 ratings)
Woodstock, Ulster County, New York, United States
Details
Vrbo
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House Woodstock
$767 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (13 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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Cottage Woodstock
$408 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (189 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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House Woodstock
$346 per night
House ∙ 8 guests ∙ 4 bedrooms
4.7
"Outstanding" (31 ratings)
Woodstock, Ulster County, New York, United States
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Vrbo
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Recommended Rentals With Pools

House Pool Woodstock
$814 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (182 ratings)
Woodstock, Ulster County, New York, United States
Pool
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Vrbo
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Apartment Pool Woodstock
$125 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (13 ratings)
Woodstock, Ulster County, New York, United States
Pool
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Vrbo
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Cottage Pool Woodstock
$449 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (22 ratings)
Woodstock, Ulster County, New York, United States
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

House Pet-friendly Woodstock
$495 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
"Excellent" (11 ratings)
Woodstock, Ulster County, New York, United States
Pet-friendly
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Vrbo
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Cottage Pet-friendly Woodstock
$255 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (96 ratings)
Woodstock, Ulster County, New York, United States
Pet-friendly
Details
Vrbo
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House Pet-friendly Woodstock
$268 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (20 ratings)
Woodstock, Ulster County, New York, United States
Pet-friendly
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Vrbo
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Best vacation rentals with a balcony

Chalet Balcony Woodstock
$399 per night
Chalet ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (173 ratings)
Woodstock, Ulster County, New York, United States
Balcony
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Vrbo
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Apartment Balcony Woodstock
$154 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (21 ratings)
Woodstock, Ulster County, New York, United States
Balcony
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Vrbo
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Cabin Balcony Woodstock
$287 per night
Cabin ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (104 ratings)
Woodstock, Ulster County, New York, United States
Balcony
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Vrbo
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Frequently Asked Questions

How much does it cost to book a vacation rental in Woodstock?

Prices for a stay in Woodstock begin at $136 per night.

Is there a wide selection of vacation rentals in Woodstock?

Tripping.com offers great selection on vacation rentals with 358 offers currently available in Woodstock.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Woodstock Information

About Woodstock

A mecca for artists in the woods of New York, Woodstock has a long history of attracting painters, musicians, and festivalgoers. It was established in 1787 by European settlers and began industrializing in the early 1800s. Though Woodstock’s reputation is preceded by the infamous festival of the same name, it actually isn’t hosted in the town. The permit for the festival was turned down in Woodstock, so it moved 60 miles away a dairy farm in Bethel. Woodstock, dubbed “the most famous small town in the world,” remains tied to its history and aims to keep the past alive in its art and preservation of natural beauty.

Things to do in Woodstock

Woodstock is full of eclectic shops that are sure to interest travelers. Shop for jewelry, handmade ceramic pieces, or even Tibetan décor. In the warmer months, be sure to stop by Mower’s Saturday Market for antiques, produce, and other unique gifts from local vendors. Whether you’re a foodie or you just enjoy a good meal, Woodstock has many fine restaurants that often offer organically sourced food and diverse menus. Try top-rated Provisions deli for a pastrami sandwich or vegan dessert. For a laid-back drink, check out The Commune Saloon, featuring a fire pit and live music. Enjoy the benefits of Woodstock’s healing community by checking out their spas and holistic studios. Visit The Emerson Spa for a relaxing massage, or check out Mountain View Studio for an interdisciplinary healing experience. Each summer, Woodstock hosts a summer concert series called Concerts on the Green, which are free concerts suitable for all ages. There is also Jazzstock, which celebrates jazz music year round. Summer visitors can also check out Maverick Concerts, the award-winning chamber music festival at a unique venue in the woods.

Day Trips from Woodstock

Nature enthusiasts will find plenty of hiking, fishing, and camping at Big Indian Wilderness. You will find the longest stretch of trail through pristine forest in the Catskill Mountains. Try the Mongaup-Hardenburg Trail for a moderately difficult hike offering opportunities for birdwatching and other animal life. Take a one-hour drive North to Albany, which is New York’s capital. Take a free tour of the capitol building, stroll through Washington Park, and stop for dinner at top-rated Athos Restaurant. History enthusiasts can’t miss a tour of Franklin Delano Roosevelt’s home. Only a 45-minute drive from Woodstock, this historic site contains the former president’s home, the Eleanor Roosevelt National Historic Site, and the Vanderbilt Mansion National Historic Site. The grounds are free to visitors, but tours start at $10 per person.

Woodstock Accommodations

A quick search on Tripping.com yields nearly 200 results for vacation rentals. Pick a spot in the woods for a secluded vacation or a spot close to the Hudson River for quick access to kayaking and canoeing. Many rentals are quaint cottages and cabins, perfect for your relaxing vacation to Woodstock.

Transportation in Woodstock

Woodstock can be reached from the East and West through New York State Route 212. Within Woodstock, there are many taxi services as well as bus service through Adirondack Pine Hill Trailways. There are also many walking trails within the town. The nearest major airport is Stewart International Airport, 48 miles away from Woodstock.

Popular Day Trips Near Woodstock

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