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Holiday Rentals in Woodstock

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Distance from

5 km
174 rentals in Woodstock.
Sioux Tipi on the waterfall, holiday rental in Woodstock
Sioux Tipi on the waterfall, holiday rental in Woodstock
Sioux Tipi on the waterfall, holiday rental in Woodstock

Sioux Tipi on the waterfall

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, holiday rental in Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, holiday rental in Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, holiday rental in Woodstock

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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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HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace, holiday rental in Woodstock
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace, holiday rental in Woodstock
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace, holiday rental in Woodstock

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

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
3 bathrooms
Sleeps 8
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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Cozy and eclectic Woodstock getaway, holiday rental in Woodstock
Cozy and eclectic Woodstock getaway, holiday rental in Woodstock
Cozy and eclectic Woodstock getaway, holiday rental in Woodstock

Cozy and eclectic Woodstock getaway

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
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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Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities), holiday rental in Woodstock
Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities), holiday rental in Woodstock
Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities), holiday rental in Woodstock

Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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chezbevet, a country cabin, holiday rental in Woodstock
chezbevet, a country cabin, holiday rental in Woodstock
chezbevet, a country cabin, holiday rental in Woodstock

chezbevet, a country cabin

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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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Frolic & Focus in this Bright Stylish Woodstock Cottage, holiday rental in Woodstock
Frolic & Focus in this Bright Stylish Woodstock Cottage, holiday rental in Woodstock
Frolic & Focus in this Bright Stylish Woodstock Cottage, holiday rental in Woodstock

Frolic & Focus in this Bright Stylish Woodstock Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hotel Woodstock - Queen Anne's Lace Suite, holiday rental in Woodstock
Hotel Woodstock - Queen Anne's Lace Suite, holiday rental in Woodstock
Hotel Woodstock - Queen Anne's Lace Suite, holiday rental in Woodstock

Hotel Woodstock - Queen Anne's Lace Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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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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
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Private entire home in center of Woodstock ~ Dogs welcome ~ Hot Tub, holiday rental in Woodstock
Private entire home in center of Woodstock ~ Dogs welcome ~ Hot Tub, holiday rental in Woodstock
Private entire home in center of Woodstock ~ Dogs welcome ~ Hot Tub, holiday rental in Woodstock

Private entire home in center of Woodstock ~ Dogs welcome ~ Hot Tub

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage, holiday rental in Woodstock
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage, holiday rental in Woodstock
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful & Spacious Woodstock Home w/ Pool, holiday rental in Woodstock
Beautiful & Spacious Woodstock Home w/ Pool, holiday rental in Woodstock
Beautiful & Spacious Woodstock Home w/ Pool, holiday rental in Woodstock

Beautiful & Spacious Woodstock Home w/ Pool

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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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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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Updated/Pet-Friendly Cabin By Hikes and Woodstock!, holiday rental in Woodstock
Updated/Pet-Friendly Cabin By Hikes and Woodstock!, holiday rental in Woodstock
Updated/Pet-Friendly Cabin By Hikes and Woodstock!, holiday rental in Woodstock

Updated/Pet-Friendly Cabin By Hikes and Woodstock!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
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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Charming Artists Cottage, holiday rental in Woodstock
Charming Artists Cottage, holiday rental in Woodstock
Charming Artists Cottage, holiday rental in Woodstock

Charming Artists Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Cottage w/ Amazing Views & Hot Tub, holiday rental in Woodstock
Modern Cottage w/ Amazing Views & Hot Tub, holiday rental in Woodstock
Modern Cottage w/ Amazing Views & Hot Tub, holiday rental in Woodstock

Modern Cottage w/ Amazing Views & Hot Tub

Holiday Rental House
2 bedrooms
1 bathroom
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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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
2 bathrooms
Sleeps 6
Match: Sleeps
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Bearsville Barn: Featured in Vogue -  Renovated Barn w/ 30 ft Ceilings and, holiday rental in Woodstock
Bearsville Barn: Featured in Vogue -  Renovated Barn w/ 30 ft Ceilings and, holiday rental in Woodstock
Bearsville Barn: Featured in Vogue -  Renovated Barn w/ 30 ft Ceilings and, holiday rental in Woodstock

Bearsville Barn: Featured in Vogue - Renovated Barn w/ 30 ft Ceilings and

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
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Hotel Woodstock - Sunflower Suite, holiday rental in Woodstock
Hotel Woodstock - Sunflower Suite, holiday rental in Woodstock
Hotel Woodstock - Sunflower Suite, holiday rental in Woodstock

Hotel Woodstock - Sunflower Suite

Condo/Apartment
1 bedroom
1 bathroom
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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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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Romantic + historic artist cottage with storybook charm in private woods!, holiday rental in Woodstock
Romantic + historic artist cottage with storybook charm in private woods!, holiday rental in Woodstock
Romantic + historic artist cottage with storybook charm in private woods!, holiday rental in Woodstock

Romantic + historic artist cottage with storybook charm in private woods!

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

Hotel Woodstock - Daisy Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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
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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
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Secluded Cabin with Hot Tub - 5 Miles to Woodstock, holiday rental in Woodstock
Secluded Cabin with Hot Tub - 5 Miles to Woodstock, holiday rental in Woodstock
Secluded Cabin with Hot Tub - 5 Miles to Woodstock, holiday rental in Woodstock

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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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
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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
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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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JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House, holiday rental in Woodstock
JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House, holiday rental in Woodstock
JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House, holiday rental in Woodstock

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The CubHouse, holiday rental in Woodstock
The CubHouse, holiday rental in Woodstock
The CubHouse, holiday rental in Woodstock

The CubHouse

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY, holiday rental in Woodstock
'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY, holiday rental in Woodstock
'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY, holiday rental in Woodstock

'A Place in the Woods' - Cabin on Chloe's Lake on 20 acres near Woodstock, NY

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serene, Backyard Oasis with Heated Pool & Hot Tub, Renovated & Clean Family Home, holiday rental in Woodstock
Serene, Backyard Oasis with Heated Pool & Hot Tub, Renovated & Clean Family Home, holiday rental in Woodstock
Serene, Backyard Oasis with Heated Pool & Hot Tub, Renovated & Clean Family Home, holiday rental in Woodstock

Serene, Backyard Oasis with Heated Pool & Hot Tub, Renovated & Clean Family Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fabulous Newly Renovated Family House Near Woodstock Center, holiday rental in Woodstock
Fabulous Newly Renovated Family House Near Woodstock Center, holiday rental in Woodstock
Fabulous Newly Renovated Family House Near Woodstock Center, holiday rental in Woodstock

Fabulous Newly Renovated Family House Near Woodstock Center

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
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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Woodstock Cottage with a view !, holiday rental in Woodstock
Woodstock Cottage with a view !, holiday rental in Woodstock
Woodstock Cottage with a view !, holiday rental in Woodstock

Woodstock Cottage with a view !

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pure Inspiration, holiday rental in Woodstock
Pure Inspiration, holiday rental in Woodstock
Pure Inspiration, holiday rental in Woodstock

Pure Inspiration

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream, holiday rental in Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream, holiday rental in Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream, holiday rental in Woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 174
Frequently Asked Questions about Woodstock