Woodstock, New York

Vacation Rentals in Woodstock, New York

Discover 98 vacation rental properties in Woodstock. From 1 to 5 bedrooms. Average $403/night. 100% have pools.

98 verified listings Book securely on VRBO Prices updated March 2026

98 properties available

Romantic Luxury Chalet With Private Pool

Romantic Luxury Chalet With Private Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$381/night
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Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres

Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres

4 beds 2 baths
PoolA/CWiFiBalcony
$617/night
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Private Home ~ All Yours ~ Newly Renovated ~ In town ~ fenced in yard ~ Quiet

Private Home ~ All Yours ~ Newly Renovated ~ In town ~ fenced in yard ~ Quiet

2 beds 1 bath
PoolA/CWiFiBalcony
$306/night
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Streamside Cottage Walking Distance to Town of Woodstock

Streamside Cottage Walking Distance to Town of Woodstock

1 bed 1 bath
PoolA/CWiFiBalcony
$207/night
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NEW! Rock City Writer's Studio: Bucolic Setting, Nordic Sauna, Walk to Town!

NEW! Rock City Writer's Studio: Bucolic Setting, Nordic Sauna, Walk to Town!

1 bath
PoolA/CWiFiBalcony
$126/night
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Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

1 bed 1 bath
PoolA/CWiFiBalcony
$171/night
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Village Center: Gracious & Spacious Retreat "Above the Books"

Village Center: Gracious & Spacious Retreat "Above the Books"

2 beds 1 bath
PoolA/CWiFiBalcony
$218/night
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JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House

JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House

2 beds 2 baths
PoolA/CWiFiBalcony
$380/night
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Private apartment suite, dedicated WiFi, easy access to Woodstock village

Private apartment suite, dedicated WiFi, easy access to Woodstock village

1 bed
PoolA/CWiFiBalcony
$117/night
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NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

1 bed 1 bath
PoolA/CWiFiBalcony
$199/night
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TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

1 bed 1 bath
PoolA/CWiFiBalcony
$291/night
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Special Summer Offer: Private Central Woodstock w/ Heated Saltwater Pool

Special Summer Offer: Private Central Woodstock w/ Heated Saltwater Pool

4 beds 4 baths
PoolA/CWiFiBalcony
$853/night
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INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views

INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views

2 beds 2 baths
PoolA/CWiFiBalcony
$452/night
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Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

3 beds 3 baths
PoolA/CWiFiBalcony
$339/night
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ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

2 beds 2 baths
PoolA/CWiFiBalcony
$291/night
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Adorable Red Cottage, walking distance to Woodstock

Adorable Red Cottage, walking distance to Woodstock

3 beds 1 bath
PoolA/CWiFiBalcony
$136/night
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Woodstock Paradise with Gardens & Private Heated Pool (seasonal)

Woodstock Paradise with Gardens & Private Heated Pool (seasonal)

2 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

2 beds 2 baths
PoolA/CWiFiBalcony
$296/night
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Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House

2 beds 1 bath
PoolA/CWiFiBalcony
$377/night
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TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$324/night
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Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

3 beds 2 baths
PoolA/CWiFiBalcony
$584/night
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Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

3 beds 2 baths
PoolA/CWiFiBalcony
$279/night
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Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

1 bath
PoolA/CWiFiBalcony
$191/night
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Bright, historic Woodstock home close to town

Bright, historic Woodstock home close to town

2 beds 1 bath
PoolA/CWiFiBalcony
$387/night
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A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access

A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access

1 bed 1 bath
PoolA/CWiFiBalcony
$267/night
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In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,

In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,

2 beds 1 bath
PoolA/CWiFiBalcony
$216/night
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Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!

Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!

3 beds 2 baths
PoolA/CWiFiBalcony
$381/night
View Details → Book on VRBO
Magical cottage in the Woodstock woods with with heated pool and firepit

Magical cottage in the Woodstock woods with with heated pool and firepit

1 bed 1 bath
PoolA/CWiFiBalcony
$357/night
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"Blissful Retreat" Elegant , Charming & Peaceful

"Blissful Retreat" Elegant , Charming & Peaceful

2 beds 1 bath
PoolA/CWiFiBalcony
$396/night
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Contemporary, Secluded Cabin in the Heart of Woodstock W/ Hot Tub & Fireplace

Contemporary, Secluded Cabin in the Heart of Woodstock W/ Hot Tub & Fireplace

1 bed 1 bath
PoolA/CWiFiBalcony
$243/night
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Luxury Woodstock Retreat: 11 Acres of Bliss w Pool

Luxury Woodstock Retreat: 11 Acres of Bliss w Pool

4 beds 3 baths
PoolA/CWiFiBalcony
$1,518/night
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Woodstock Sanctuary Spa Retreat - walk to town!

Woodstock Sanctuary Spa Retreat - walk to town!

2 beds 1 bath
PoolA/CWiFiBalcony
$362/night
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Gracious Woodstock Retreat -Walking Distance to Town

Gracious Woodstock Retreat -Walking Distance to Town

4 beds 3 baths
PoolA/CWiFiBalcony
$447/night
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Cozy Woodstock Home w/ Fire Pit!

Cozy Woodstock Home w/ Fire Pit!

1 bed 1 bath
PoolA/CWiFiBalcony
$243/night
View Details → Book on VRBO
NEW! Woodstock-Private-Exquisite-Modern A-Frame-Minimum Stays are Monthly!

NEW! Woodstock-Private-Exquisite-Modern A-Frame-Minimum Stays are Monthly!

5 beds 3 baths
PoolA/CWiFiBalcony
$497/night
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A pleasant space in a pleasant neighborhood in a beautiful part of the country!

A pleasant space in a pleasant neighborhood in a beautiful part of the country!

2 beds 1 bath
PoolA/CWiFiBalcony
$251/night
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MONTH! History+art+luxury+style=Byrdcliffe Retreat w/separate office+heated pool

MONTH! History+art+luxury+style=Byrdcliffe Retreat w/separate office+heated pool

3 beds 2 baths
PoolA/CWiFiBalcony
$828/night
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Spacious, Private, Close to Town, Work From Home

Spacious, Private, Close to Town, Work From Home

3 beds 2 baths
PoolA/CWiFiBalcony
$450/night
View Details → Book on VRBO
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

3 beds 2 baths
PoolA/CWiFiBalcony
$340/night
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Modern Glass House, Minutes to Town

Modern Glass House, Minutes to Town

3 beds 3 baths
PoolA/CWiFiBalcony
$1,548/night
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Spa ranch | hot tub, steam, wetroom, chef kitchen

Spa ranch | hot tub, steam, wetroom, chef kitchen

3 beds 2 baths
PoolA/CWiFiBalcony
$753/night
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Woodstock Historic Artist Estate. The Museum House

Woodstock Historic Artist Estate. The Museum House

3 beds 2 baths
PoolA/CWiFiBalcony
$999/night
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Walk To Woodstock, Streamside W/In Ground Pool

Walk To Woodstock, Streamside W/In Ground Pool

5 beds 5 baths
PoolA/CWiFiBalcony
$2,210/night
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Serene Woodstock Cottage & Studio - Right In Town

Serene Woodstock Cottage & Studio - Right In Town

3 beds 2 baths
PoolA/CWiFiBalcony
$246/night
View Details → Book on VRBO
LIVE IN NATURE - WALK TO TOWN- CHILDREN LOVE US- SIT BY THE CAMP FIRE

LIVE IN NATURE - WALK TO TOWN- CHILDREN LOVE US- SIT BY THE CAMP FIRE

1 bed 1 bath
PoolA/CWiFiBalcony
$199/night
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Fabulous Newly Renovated Family House Near Woodstock Center

Fabulous Newly Renovated Family House Near Woodstock Center

4 beds 3 baths
PoolA/CWiFiBalcony
$424/night
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Serene Woodstock 3 bedroom cottage with sweeping mountain views

Serene Woodstock 3 bedroom cottage with sweeping mountain views

3 beds 2 baths
PoolA/CWiFiBalcony
$321/night
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Cheerful, renovated 4 bedroom, 10 min walk to town

Cheerful, renovated 4 bedroom, 10 min walk to town

4 beds 1 bath
PoolA/CWiFiBalcony
$481/night
View Details → Book on VRBO

Showing 48 of 98 properties

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