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Vacation Rentals in Woodstock, New York

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about Woodstock

Woodstock, New York Vacation Rentals and Tourism

The massive 1969 rock concert that’s associated with Woodstock, New York actually occurred 50 miles away. But the out-of-town festivities do give you an idea of what to expect with Woodstock vacation rentals. Tap into your inner hippie by staying a Woodstock vacation rental…

Great affordable Woodstock lodging may be music to your ears, but expect your senses to be overloaded at the start of your Woodstock, New York vacation. That’s because music is everywhere! But art in general flourishes in and around Woodstock vacation rentals. After all, decades before Woodstock got the reputation of being a haven for hippies, it was a thriving artistic community and it still is to this day. So hunker down in a Woodstock lake cabin rental or vacation home and give into the carefree spirit of the area.

Bob Dylan, Van Morrison, Cat Stevens, and many other classic musicians, have composed tunes in this inspiring town. See what kinds of creativity Woodstock vacation cabins can coax out of you!

Woodstock Vacation Rental Deals

When you vacation in Woodstock, you’ll discover that the ways to explore, have fun and relax are endless. But there's for sure one way that you can save money while you're there no matter what activities you choose, and that is by staying in an affordable Woodstock rental home. There are countless cheap Woodstock beach homes, condos, and villas to choose from and they’re all reasonably priced. We can accommodate a group or a budget of any size and are confident with our good deals on Woodstock accommodation, that you won’t break the bank on your next trip.

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Woodstock Handmade Log Cabin
Woodstock Cabin Rental Picture
  • bedrooms 2
  • community
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $200 - $225 /nt
    $750 - $850 /wk
    $2,800 - $3,000 /mth
 
 
 
 
 

5 reviews write a review

Charming Artist's Cottage
Woodstock House Rental Picture
  • bedrooms 2
  • community Woodstock, NY
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $150 - $250 /nt
    $950 - $1,250 /wk
 
 
 
 
 

2 reviews write a review

The Waterfall House
Woodstock House Rental Picture
  • bedrooms 2
  • community Catskill Mountains
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $350 - $400 /nt
    $2,300 - $2,700 /wk
    $6,000 - $9,800 /mth
 
 
 
 
 

49 reviews write a review

Catskills-Retreat
Woodstock House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $295 - $695 /nt
    $995 - $1,500 /wk
    $3,200 - $3,600 /mth
 
 
 
 
 

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Woodstook Design Waterfront, Deck, Private Dock Kayak. Swim
Woodstock House Rental Picture
  • bedrooms 2
  • community Hudson Valley
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $132 - $420 /nt
    $1,050 - $2,300 /wk
    $5,800 - $8,400 /mth
 
 
 
 
 

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Romantic Streamside Cottage
Woodstock House Rental Picture
  • bedrooms 2
  • community Village of Woodstock
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $400 /nt
    $1,200 - $1,500 /wk
    $3,600 - $4,800 /mth
 
 
 
 
 

1 reviews write a review

Family Fun in Private Paradise
Woodstock House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $300 - $320 /nt
    $2,000 - $2,200 /wk
 
 
 
 
 

8 reviews write a review

Breathe the Country Air
Woodstock House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 11
  • baths
  • rates (USD) $325 - $650 /nt
    $2,500 - $3,000 /wk
    $4,800 - $5,250 /mth
 
 
 
 
 

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Privacy & Luxury @ Heart of Woodstock w/Hot Tub
Woodstock House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $250 - $295 /nt
    $1,855 - $2,000 /wk
    $4,900 - $5,850 /mth
 
 
 
 
 

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Romantic Chalet with Saltwater Pool
Woodstock Chalet Rental Picture
  • bedrooms 0
  • rental type Chalet
  • sleeps 2
  • baths 1
  • rates (USD) $195 - $275 /nt
    $1,225 - $1,925 /wk
    $7,500 /mth
 
 
 
 
 

6 reviews write a review

The Ultimate Country Escape For City-folk By City-folk - All Amenities Luxury
Woodstock Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • sleeps 14
  • baths 3
  • rates (USD) $360 - $475 /nt
    $2,750 /wk
    $10,500 /mth
 
 
 
 
 

1 reviews write a review

Wonderful Farmhouse...Walk to Woodstock
Woodstock Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $338 /nt
 
 
 
 
 

5 reviews write a review

Dancing Angel: Sunny Mountainside Cottage with World-Class Views!
Woodstock Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $175 - $195 /nt
    $975 - $1,175 /wk
 
 
 
 
 

12 reviews write a review

STYLISH HOT TUB VILLA IN TOWN, GARDEN, DECK, Steam Room, Sleeps 2-7
Woodstock House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $199 /nt
 
 
 
 
 

39 reviews write a review

As seen in Cottage Style Magazine Woodstock Stone home walk to swim lake, ski
Woodstock Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $395 - $550 /nt
    $2,600 - $3,500 /wk
 
 
 
 
 

29 reviews write a review

2BR Cabin, Hot Tub, Fireplace, in the Heart of Woodstock
Woodstock Cabin Rental Picture
  • bedrooms 2
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $225 - $275 /nt
    $1,500 /wk
    $4,500 /mth
 
 
 
 
 

3 reviews write a review

Secluded, Luxury Home with Hot Tub
Woodstock House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $225 - $295 /nt
    $1,700 - $1,850 /wk
    $4,500 - $5,100 /mth
 
 
 
 
 

4 reviews write a review

A Romantic Escape, a Luxury Barn in Woodstock
Woodstock Barn Rental Picture
  • bedrooms 1
  • rental type Barn
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $195 - $245 /nt
    $1,250 - $1,350 /wk
 
 
 
 
 

10 reviews write a review

POOL , HOT TUB & FIRE PLACE
Woodstock House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $350 - $450 /nt
    $3,150 /wk
    $12,500 /mth
 
 
 
 
 

12 reviews write a review

Romantic Hidden Gem w/ Mt. Views, walk to town
Woodstock Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $150 - $275 /nt
 
 
 
 
 

23 reviews write a review

Catskills, HITS, Woodstock, Saugerties, Secluded Yet Close To All
Woodstock Chateau_/_country_house Rental Picture
  • bedrooms 4
  • rental type Chateau / country house
  • sleeps 8
  • baths
  • rates (USD) $400 - $500 /nt
    $2,500 - $3,000 /wk
    $7,500 - $9,000 /mth
 
 
 
 
 

4 reviews write a review

As seen on HGTV!! Renovated 2 story Farmhouse on 4 Acres/Meadow/Mountain views!
Woodstock House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $350 /nt
    $1,750 /wk
    $6,300 /mth
 
 
 
 
 

19 reviews write a review

'I found myself in a strange and wondrous place......'
Woodstock House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 4
  • rates (USD) $375 - $450 /nt
    $2,250 - $2,550 /wk
    $7,200 - $9,180 /mth
 
 
 
 
 

19 reviews write a review

NEW! FIRST TIME OFFERED! INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views
Woodstock Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $265 - $350 /nt
    $1,540 - $1,750 /wk
 
 
 
 
 

15 reviews write a review

Gorgeous Woodstock Chalet + Hot Tub, optional Guest House, Sleeps 12-16
Woodstock Chateau_/_country_house Rental Picture
  • bedrooms 5
  • rental type Chateau / country house
  • owner badgeowner badge
  • sleeps 16
  • baths 4
  • rates (USD)
 
 
 
 
 

7 reviews write a review

Spectacular, Luxurious Home on 12 acres w/ Mountain Views, Privacy, Space
Woodstock House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD)
 
 
 
 
 

7 reviews write a review

Nethermead Woodstock
Woodstock House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $350 /nt
    $1,750 /wk
 
 
 
 
 

8 reviews write a review

Modern Barn Getaway Near Woodstock
Woodstock House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $350 - $750 /nt
    $2,400 - $3,000 /wk
    $9,000 - $12,000 /mth
 
 
 
 
 

27 reviews write a review

Imagine Woodstock Historic Mill house
Woodstock Mill Rental Picture
  • bedrooms 2
  • rental type Mill
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $190 - $325 /nt
    $1,490 /wk
    $3,900 /mth
 
 
 
 
 

8 reviews write a review

WOODSTOCK TREEHOUSE near CATSKILLS, SAUGERTIES, HITS, secluded yet close to all
Woodstock Chateau_/_country_house Rental Picture
  • bedrooms 4
  • rental type Chateau / country house
  • sleeps 9
  • baths 2
  • rates (USD) $450 - $500 /nt
    $2,750 - $3,000 /wk
    $8,000 - $9,000 /mth
 
 
 
 
 

10 reviews write a review

Woodstock Treehouse Near Catskills, Saugerties, Hits, Secluded Yet Close To All
Woodstock Chateau_/_country_house Rental Picture
  • bedrooms 4
  • rental type Chateau / country house
  • sleeps 9
  • baths 2
  • rates (USD) $450 - $500 /nt
    $2,750 - $3,000 /wk
    $8,000 - $9,000 /mth
 
 
 
 
 

3 reviews write a review

Classic Catskills Estate on Private Mountain, with Available Guest House
Woodstock House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 13
  • baths 3
  • rates (USD) $300 - $500 /nt
 
 
 
 
 

10 reviews write a review

Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock
Woodstock Cabin Rental Picture
  • bedrooms 4
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $300 - $450 /nt
    $1,950 - $1,995 /wk
 
 
 
 
 

50 reviews write a review

As Seen on HGTV's House Hunters - Heartwarming Cedar Cottage + Hot Tub
Woodstock Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $200 - $300 /nt
    $1,400 /wk
    $4,000 /mth
 
 
 
 
 

6 reviews write a review

One Of The Best Houses In Woodstock (Great for Catskills Skiing)
Woodstock Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $250 - $500 /nt
    $1,350 - $2,750 /wk
    $5,785 - $10,240 /mth
 
 
 
 
 

18 reviews write a review

Spanish Style Five Bedroom with In Ground Pool, Cinema Room and Woods
Woodstock Chateau_/_country_house Rental Picture
  • bedrooms 5
  • rental type Chateau / country house
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $450 /nt
    $2,450 /wk
    $9,000 /mth
 
 
 
 
 

5 reviews write a review

Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Village Green!
Woodstock Bungalow Rental Picture
  • bedrooms 3
  • rental type Bungalow
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $325 - $375 /nt
    $1,950 - $2,250 /wk
 
 
 
 
 

11 reviews write a review

Privacy And Comfort With Modern Amenities
Woodstock House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $235 /nt
    $1,175 /wk
    $3,525 /mth
 
 
 
 
 

2 reviews write a review

A WOODSTOCK FAMILY FAVORITE – Private, yet near everything!
Woodstock House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $299 /nt
    $2,075 /wk
 
 
 
 
 

5 reviews write a review

SPECIAL WINTER PRICING Luxurious, Private, Romantic, Skiers welcome, Magical
Woodstock House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $236 - $450 /nt
    $2,250 - $2,700 /wk
    $5,000 - $10,200 /mth
 
 
 
 
 

3 reviews write a review

Beautiful Woodstock Mountain House with Hot Tub and Ping Pong
Woodstock House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $295 - $350 /nt
    $1,500 - $1,800 /wk
    $3,500 - $5,000 /mth
 
 
 
 
 

7 reviews write a review

Awesome!! 'The Gift', Hot Tub, W/BFireplace,Steam Rm
Woodstock Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $399 /nt
 
 
 
 
 

110 reviews write a review

THE NEST: Sunny studio w/skylights, pool, walk to village green + NYC bus !
Woodstock Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $115 - $145 /nt
    $750 - $875 /wk
 
 
 
 
 

18 reviews write a review

Minutes To Hits, Woodstock, Saugerties, Thruway Exit 19
Woodstock Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • sleeps 8
  • baths 2
  • rates (USD) $325 - $400 /nt
    $2,000 - $2,500 /wk
    $6,000 - $7,500 /mth
 
 
 
 
 

2 reviews write a review

Woodstock, Saugerties, Catskills, HITS, Kingston, Eclectic Wooded Escape
Woodstock Farmhouse Rental Picture
  • bedrooms 3
  • rental type Farmhouse
  • sleeps 7
  • baths 2
  • rates (USD) $275 - $300 /nt
    $1,500 - $1,800 /wk
    $4,500 - $5,500 /mth
 
 
 
 
 

1 reviews write a review

Stunning Contemporary Country Home With Salt Water Pool In Woodstock Ny
Woodstock House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 7
  • baths 3
  • rates (USD) $550 /nt
    $3,500 /wk
    $14,000 /mth
 
 
 
 
 

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Eastwoods, Luxury, Nature, Privacy, Comfort,Hiking,Skiing,Peace...
Woodstock House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

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Quaint Woodstock Cottage
Woodstock Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $135 /nt
    $945 /wk
    $3,780 /mth
 
 
 
 
 

7 reviews write a review

Historic Farmhouse, Secluded Yet Steps Away from Village Green
Woodstock Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $400 - $425 /nt
    $2,000 /wk
 
 
 
 
 

4 reviews write a review