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Holiday Rentals in Woodstock

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179 rentals in Woodstock.
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Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong, holiday rental in Woodstock
Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong, holiday rental in Woodstock
Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong, holiday rental in Woodstock

Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room, holiday rental in Woodstock
1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room, holiday rental in Woodstock
1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room, holiday 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
Match: Sleeps
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Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!, holiday rental in Woodstock
Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!, holiday rental in Woodstock
Woodstock's Brook Cottage: TOP-RATED streamside luxury, fireplace, walk-to-town!, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views, holiday rental in Woodstock
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views, holiday rental in Woodstock
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views, holiday rental in Woodstock

INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views

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

Romantic Luxury Chalet with Private Pool

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

Streamside Cottage Walking Distance to Town of Woodstock

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Woodstock Mountain House with Hot Tub and Ping Pong, holiday rental in Woodstock
Beautiful Woodstock Mountain House with Hot Tub and Ping Pong, holiday rental in Woodstock
Beautiful Woodstock Mountain House with Hot Tub and Ping Pong, holiday rental in Woodstock

Beautiful Woodstock Mountain House with Hot Tub and Ping Pong

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock, holiday rental in Woodstock
Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock, holiday rental in Woodstock
Secluded, Renovated Cabin with Hot Tub - 5 Miles to Woodstock, holiday rental in Woodstock

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

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

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

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

Charming Artist's Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, holiday rental in Woodstock
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, holiday rental in Woodstock
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, holiday rental in Woodstock

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access, holiday rental in Woodstock
A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access, holiday rental in Woodstock
A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access, holiday rental in Woodstock

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, holiday rental in Woodstock
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, holiday rental in Woodstock
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!, holiday 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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Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!, holiday rental in Woodstock
Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!, holiday rental in Woodstock
Romantic + historic artist’s cottage in private woods ~ wake up to birdsong!, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Magical Chalet with spectacular views, holiday rental in Woodstock
Magical Chalet with spectacular views, holiday rental in Woodstock
Magical Chalet with spectacular views, holiday rental in Woodstock

Magical Chalet with spectacular views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag, holiday rental in Woodstock
Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag, holiday rental in Woodstock
Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag, holiday rental in Woodstock

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

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

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

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

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, holiday rental in Woodstock
Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, holiday rental in Woodstock
Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, holiday rental in Woodstock

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Village Center: Gracious & Spacious Retreat "Above the Books", holiday rental in Woodstock
Village Center: Gracious & Spacious Retreat "Above the Books", holiday rental in Woodstock
Village Center: Gracious & Spacious Retreat "Above the Books", holiday 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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Contemporary, Secluded Cabin in the Heart of  Woodstock W/ Hot Tub & Fireplace, holiday rental in Woodstock
Contemporary, Secluded Cabin in the Heart of  Woodstock W/ Hot Tub & Fireplace, holiday rental in Woodstock
Contemporary, Secluded Cabin in the Heart of  Woodstock W/ Hot Tub & Fireplace, holiday rental in Woodstock

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Gracious Woodstock Retreat -Walking Distance to Town, holiday rental in Woodstock
Gracious Woodstock Retreat -Walking Distance to Town, holiday rental in Woodstock
Gracious Woodstock Retreat -Walking Distance to Town, holiday rental in Woodstock

Gracious Woodstock Retreat -Walking Distance to Town

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Private Home, Mins. to Woodstock, holiday rental in Woodstock
Private Home, Mins. to Woodstock, holiday rental in Woodstock
Private Home, Mins. to Woodstock, holiday rental in Woodstock

Private Home, Mins. to Woodstock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Pet Friendly Cabin Doh-Ray up  * 1500 ft, holiday rental in Woodstock
Pet Friendly Cabin Doh-Ray up  * 1500 ft, holiday rental in Woodstock
Pet Friendly Cabin Doh-Ray up  * 1500 ft, holiday rental in Woodstock

Pet Friendly Cabin Doh-Ray up * 1500 ft

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre, holiday rental in Woodstock
Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre, holiday rental in Woodstock
Family-Friendly Retreat Close to Town w/ Heated Pool, Hot Tub on Nearly 3 Acre, holiday 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
Match: Sleeps
More info
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Romantic Country Barn By the Stream, holiday rental in Woodstock
Romantic Country Barn By the Stream, holiday rental in Woodstock
Romantic Country Barn By the Stream, holiday rental in Woodstock

Romantic Country Barn By the Stream

Cabin Holiday Rental
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Privacy & Luxury * Heart of Woodstock w/ Hot Tub, holiday rental in Woodstock
Privacy & Luxury * Heart of Woodstock w/ Hot Tub, holiday rental in Woodstock
Privacy & Luxury * Heart of Woodstock w/ Hot Tub, holiday rental in Woodstock

Privacy & Luxury * Heart of Woodstock w/ Hot Tub

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

Country Cabin in Woodstock, NY- Cozy and Pet Friendly

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!, holiday rental in Woodstock
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!, holiday rental in Woodstock
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!, holiday rental in Woodstock

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!, holiday rental in Woodstock
Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!, holiday rental in Woodstock
Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!, holiday rental in Woodstock

Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard, holiday rental in Woodstock
Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard, holiday rental in Woodstock
Work & Play with your Pup in Woodstock! High Speed WiFi~Hot Tub ~ Fenced in yard, holiday 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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NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable, holiday rental in Woodstock
NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable, holiday rental in Woodstock
NEW romantic/luxe Woodstock designer hideaway skylit, AC, firepit, walkable, holiday 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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Woodstock House on 35 private acres Mtn Views, holiday rental in Woodstock
Woodstock House on 35 private acres Mtn Views, holiday rental in Woodstock
Woodstock House on 35 private acres Mtn Views, holiday rental in Woodstock

Woodstock House on 35 private acres Mtn Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, holiday rental in Woodstock
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, holiday rental in Woodstock
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock, holiday rental in Woodstock
Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock, holiday rental in Woodstock
Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock, holiday rental in Woodstock

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Wydeclove Artist Retreat, holiday rental in Woodstock
Wydeclove Artist Retreat, holiday rental in Woodstock
Wydeclove Artist Retreat, holiday rental in Woodstock

Wydeclove Artist Retreat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lovely Woodstock Home, Private, Walk to Town - Family friendly, holiday rental in Woodstock
Lovely Woodstock Home, Private, Walk to Town - Family friendly, holiday rental in Woodstock
Lovely Woodstock Home, Private, Walk to Town - Family friendly, holiday rental in Woodstock

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!, holiday rental in Woodstock
Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!, holiday rental in Woodstock
Mountain Stream Retreat: rustic elegance, decks overlooking stream, wood stove!, holiday rental in Woodstock

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, holiday rental in Woodstock
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, holiday rental in Woodstock
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, holiday rental in Woodstock

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Custom Post and Beam Home on Private Stream, holiday rental in Woodstock
Custom Post and Beam Home on Private Stream, holiday rental in Woodstock
Custom Post and Beam Home on Private Stream, holiday rental in Woodstock

Custom Post and Beam Home on Private Stream

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Woodstock Historic Artist Estate - The Carriage House, holiday rental in Woodstock
Woodstock Historic Artist Estate - The Carriage House, holiday rental in Woodstock
Woodstock Historic Artist Estate - The Carriage House, holiday rental in Woodstock

Woodstock Historic Artist Estate - The Carriage House

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views, holiday rental in Woodstock
Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views, holiday rental in Woodstock
Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Walk To Woodstock, Streamside W/In Ground Pool, holiday rental in Woodstock
Walk To Woodstock, Streamside W/In Ground Pool, holiday rental in Woodstock
Walk To Woodstock, Streamside W/In Ground Pool, holiday rental in Woodstock

Walk To Woodstock, Streamside W/In Ground Pool

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Mid-Century Gem with Heated Pool 1 Mile from Town, holiday rental in Woodstock
Mid-Century Gem with Heated Pool 1 Mile from Town, holiday rental in Woodstock
Mid-Century Gem with Heated Pool 1 Mile from Town, holiday rental in Woodstock

Mid-Century Gem with Heated Pool 1 Mile from Town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Hikers Haven Romantic Mountaintop Studio� holidaysSki�Private10 acres, holiday rental in Woodstock
Hikers Haven Romantic Mountaintop Studio� holidaysSki�Private10 acres, holiday rental in Woodstock
Hikers Haven Romantic Mountaintop Studio� holidaysSki�Private10 acres, holiday rental in Woodstock

Hikers Haven Romantic Mountaintop Studio� holidaysSki�Private10 acres

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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NEW! Rock City Writer's Studio: Bucolic Setting, , holiday rental in Woodstock
NEW! Rock City Writer's Studio: Bucolic Setting, , holiday rental in Woodstock
NEW! Rock City Writer's Studio: Bucolic Setting, , holiday rental in Woodstock

NEW! Rock City Writer's Studio: Bucolic Setting,

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,, holiday rental in Woodstock
In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,, holiday rental in Woodstock
In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hotel Woodstock - Tiger Lilly Suite, holiday rental in Woodstock
Hotel Woodstock - Tiger Lilly Suite, holiday rental in Woodstock
Hotel Woodstock - Tiger Lilly Suite, holiday rental in Woodstock

Hotel Woodstock - Tiger Lilly Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Secluded, Luxury Home with Hot Tub, holiday rental in Woodstock
Secluded, Luxury Home with Hot Tub, holiday rental in Woodstock
Secluded, Luxury Home with Hot Tub, holiday rental in Woodstock

Secluded, Luxury Home with Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hotel Woodstock - Iris Suite, holiday rental in Woodstock
Hotel Woodstock - Iris Suite, holiday rental in Woodstock
Hotel Woodstock - Iris Suite, holiday rental in Woodstock

Hotel Woodstock - Iris Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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