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Woodstock Vacation Rentals

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176 rentals in Woodstock.
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Romantic Country Barn By the Stream, vacation rental in Woodstock
Romantic Country Barn By the Stream, vacation rental in Woodstock
Romantic Country Barn By the Stream, vacation rental in Woodstock

Romantic Country Barn By the Stream

Cabin Holiday Rental
2 bedrooms
1 bathroom
Sleeps 4
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Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!, vacation rental in Woodstock
Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!, vacation rental in Woodstock
Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!, vacation rental in Woodstock

Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room, vacation rental in Woodstock
1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room, vacation rental in Woodstock
1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room, vacation rental in Woodstock

1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views, vacation rental in Woodstock
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views, vacation rental in Woodstock
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views, vacation rental in Woodstock

INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Romantic Luxury Chalet with Private Pool, vacation rental in Woodstock
Romantic Luxury Chalet with Private Pool, vacation rental in Woodstock
Romantic Luxury Chalet with Private Pool, vacation rental in Woodstock

Romantic Luxury Chalet with Private Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Streamside Cottage Walking Distance to Town of Woodstock, vacation rental in Woodstock
Streamside Cottage Walking Distance to Town of Woodstock, vacation rental in Woodstock
Streamside Cottage Walking Distance to Town of Woodstock, vacation rental in Woodstock

Streamside Cottage Walking Distance to Town of Woodstock

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, vacation rental in Woodstock
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, vacation rental in Woodstock
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, vacation rental in Woodstock

SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Beautiful Woodstock Mountain House with Hot Tub and Ping Pong, vacation rental in Woodstock
Beautiful Woodstock Mountain House with Hot Tub and Ping Pong, vacation rental in Woodstock
Beautiful Woodstock Mountain House with Hot Tub and Ping Pong, vacation rental in Woodstock

Beautiful Woodstock Mountain House with Hot Tub and Ping Pong

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Charming Artist's Cottage, vacation rental in Woodstock
Charming Artist's Cottage, vacation rental in Woodstock
Charming Artist's Cottage, vacation rental in Woodstock

Charming Artist's Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock, vacation rental in Woodstock
Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock, vacation rental in Woodstock
Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock, vacation rental in Woodstock

Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
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Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!, vacation rental in Woodstock
Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!, vacation rental in Woodstock
Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!, vacation rental in Woodstock

Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Magical Chalet with spectacular views, vacation rental in Woodstock
Magical Chalet with spectacular views, vacation rental in Woodstock
Magical Chalet with spectacular views, vacation rental in Woodstock

Magical Chalet with spectacular views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!, vacation rental in Woodstock
Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!, vacation rental in Woodstock
Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!, vacation rental in Woodstock

Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag, vacation rental in Woodstock
Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag, vacation rental in Woodstock
Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag, vacation rental in Woodstock

Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!, vacation rental in Woodstock
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!, vacation rental in Woodstock
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!, vacation rental in Woodstock

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock, vacation rental in Woodstock
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock, vacation rental in Woodstock
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock, vacation rental in Woodstock

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
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Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, vacation rental in Woodstock
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, vacation rental in Woodstock
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, vacation rental in Woodstock

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Village Center: Gracious & Spacious Retreat 'Above the Books', vacation rental in Woodstock
Village Center: Gracious & Spacious Retreat 'Above the Books', vacation rental in Woodstock
Village Center: Gracious & Spacious Retreat 'Above the Books', vacation rental in Woodstock

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Home, Mins. to Woodstock, vacation rental in Woodstock
Private Home, Mins. to Woodstock, vacation rental in Woodstock
Private Home, Mins. to Woodstock, vacation rental in Woodstock

Private Home, Mins. to Woodstock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre, vacation rental in Woodstock
Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre, vacation rental in Woodstock
Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre, vacation rental in Woodstock

Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable, vacation rental in Woodstock
NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable, vacation rental in Woodstock
NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable, vacation rental in Woodstock

NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Contemporary, Secluded Cabin in the Heart of  Woodstock W/ Hot Tub & Fireplace, vacation rental in Woodstock
Contemporary, Secluded Cabin in the Heart of  Woodstock W/ Hot Tub & Fireplace, vacation rental in Woodstock
Contemporary, Secluded Cabin in the Heart of  Woodstock W/ Hot Tub & Fireplace, vacation rental in Woodstock

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Pet Friendly Cabin Doh-Ray up  * 1500 ft, vacation rental in Woodstock
Pet Friendly Cabin Doh-Ray up  * 1500 ft, vacation rental in Woodstock
Pet Friendly Cabin Doh-Ray up  * 1500 ft, vacation rental in Woodstock

Pet Friendly Cabin Doh-Ray up * 1500 ft

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gracious Woodstock Retreat -Walking Distance to Town, vacation rental in Woodstock
Gracious Woodstock Retreat -Walking Distance to Town, vacation rental in Woodstock
Gracious Woodstock Retreat -Walking Distance to Town, vacation rental in Woodstock

Gracious Woodstock Retreat -Walking Distance to Town

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock, vacation rental in Woodstock
Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock, vacation rental in Woodstock
Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock, vacation rental in Woodstock

Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard, vacation rental in Woodstock
Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard, vacation rental in Woodstock
Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard, vacation rental in Woodstock

Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SPRING at CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, vacation rental in Woodstock
SPRING at CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, vacation rental in Woodstock
SPRING at CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, vacation rental in Woodstock

SPRING at CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!, vacation rental in Woodstock
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!, vacation rental in Woodstock
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!, vacation rental in Woodstock

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Woodstock House on 35 private acres Mtn Views, vacation rental in Woodstock
Woodstock House on 35 private acres Mtn Views, vacation rental in Woodstock
Woodstock House on 35 private acres Mtn Views, vacation rental in Woodstock

Woodstock House on 35 private acres Mtn Views

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Privacy & Luxury * Heart of Woodstock w/ Hot Tub, vacation rental in Woodstock
Privacy & Luxury * Heart of Woodstock w/ Hot Tub, vacation rental in Woodstock
Privacy & Luxury * Heart of Woodstock w/ Hot Tub, vacation rental in Woodstock

Privacy & Luxury * Heart of Woodstock w/ Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Country Cabin in Woodstock, NY- Cozy and Pet Friendly, vacation rental in Woodstock
Country Cabin in Woodstock, NY- Cozy and Pet Friendly, vacation rental in Woodstock
Country Cabin in Woodstock, NY- Cozy and Pet Friendly, vacation rental in Woodstock

Country Cabin in Woodstock, NY- Cozy and Pet Friendly

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views, vacation rental in Woodstock
Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views, vacation rental in Woodstock
Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views, vacation rental in Woodstock

Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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Lovely Woodstock Home, Private, Walk to Town - Family friendly, vacation rental in Woodstock
Lovely Woodstock Home, Private, Walk to Town - Family friendly, vacation rental in Woodstock
Lovely Woodstock Home, Private, Walk to Town - Family friendly, vacation rental in Woodstock

Lovely Woodstock Home, Private, Walk to Town - Family friendly

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, vacation rental in Woodstock
Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, vacation rental in Woodstock
Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, vacation rental in Woodstock

Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Mountain Gardens  - DOGS �- welcome It’s Autumn � ����enjoy the fire, vacation rental in Woodstock
Mountain Gardens  - DOGS �- welcome It’s Autumn � ����enjoy the fire, vacation rental in Woodstock
Mountain Gardens  - DOGS �- welcome It’s Autumn � ����enjoy the fire, vacation rental in Woodstock

Mountain Gardens - DOGS �- welcome It’s Autumn � ����enjoy the fire

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!, vacation rental in Woodstock
Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!, vacation rental in Woodstock
Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!, vacation rental in Woodstock

Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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As Seen on HGTV's House Hunters & NY Times- Woodstock Cedar Cottage + Hot Tub, vacation rental in Woodstock
As Seen on HGTV's House Hunters & NY Times- Woodstock Cedar Cottage + Hot Tub, vacation rental in Woodstock
As Seen on HGTV's House Hunters & NY Times- Woodstock Cedar Cottage + Hot Tub, vacation rental in Woodstock

As Seen on HGTV's House Hunters & NY Times- Woodstock Cedar Cottage + Hot Tub

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, vacation rental in Woodstock
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, vacation rental in Woodstock
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, vacation rental in Woodstock

COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Hikers Haven Romantic Mountaintop Studio❤️Pool�♀️ SWIM��3 min from, vacation rental in Woodstock
Hikers Haven Romantic Mountaintop Studio❤️Pool�♀️ SWIM��3 min from, vacation rental in Woodstock
Hikers Haven Romantic Mountaintop Studio❤️Pool�♀️ SWIM��3 min from, vacation rental in Woodstock

Hikers Haven Romantic Mountaintop Studio❤️Pool�♀️ SWIM��3 min from

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Mid-Century Gem with Heated Pool 1 Mile from Town, vacation rental in Woodstock
Mid-Century Gem with Heated Pool 1 Mile from Town, vacation rental in Woodstock
Mid-Century Gem with Heated Pool 1 Mile from Town, vacation rental in Woodstock

Mid-Century Gem with Heated Pool 1 Mile from Town

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Updated/Pet-Friendly Cabin By Hikes and Woodstock!, vacation rental in Woodstock
Updated/Pet-Friendly Cabin By Hikes and Woodstock!, vacation rental in Woodstock
Updated/Pet-Friendly Cabin By Hikes and Woodstock!, vacation rental in Woodstock

Updated/Pet-Friendly Cabin By Hikes and Woodstock!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Woodstock Historic Artist Estate - The Carriage House, vacation rental in Woodstock
Woodstock Historic Artist Estate - The Carriage House, vacation rental in Woodstock
Woodstock Historic Artist Estate - The Carriage House, vacation rental in Woodstock

Woodstock Historic Artist Estate - The Carriage House

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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Relax and stay awhile, vacation rental in Woodstock
Relax and stay awhile, vacation rental in Woodstock
Relax and stay awhile, vacation rental in Woodstock

Relax and stay awhile

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Modern Farmhouse Getaway, vacation rental in Woodstock
A Modern Farmhouse Getaway, vacation rental in Woodstock
A Modern Farmhouse Getaway, vacation rental in Woodstock

A Modern Farmhouse Getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Secluded, Luxury Home with Hot Tub, vacation rental in Woodstock
Secluded, Luxury Home with Hot Tub, vacation rental in Woodstock
Secluded, Luxury Home with Hot Tub, vacation rental in Woodstock

Secluded, Luxury Home with Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded  family retreat- new pool for 2022, vacation rental in Woodstock
Secluded  family retreat- new pool for 2022, vacation rental in Woodstock
Secluded  family retreat- new pool for 2022, vacation rental in Woodstock

Secluded family retreat- new pool for 2022

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Woodstock Mediterranean Retreat, vacation rental in Woodstock
Woodstock Mediterranean Retreat, vacation rental in Woodstock
Woodstock Mediterranean Retreat, vacation rental in Woodstock

Woodstock Mediterranean Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hotel Woodstock - Tiger Lilly Suite, vacation rental in Woodstock
Hotel Woodstock - Tiger Lilly Suite, vacation rental in Woodstock
Hotel Woodstock - Tiger Lilly Suite, vacation rental in Woodstock

Hotel Woodstock - Tiger Lilly Suite

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wydeclove Artist Retreat, vacation rental in Woodstock
Wydeclove Artist Retreat, vacation rental in Woodstock
Wydeclove Artist Retreat, vacation rental in Woodstock

Wydeclove Artist Retreat

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski, vacation rental in Woodstock
Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski, vacation rental in Woodstock
Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski, vacation rental in Woodstock

Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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