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Woodstock Holiday Rentals

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117 rentals in Woodstock.
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Charming Artist's Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Romantic Country Barn By the Stream

Cabin Holiday Rental
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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Romantic Luxury Chalet for Two

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 House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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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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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A Romantic Escape, Woodstock Barn by A Stream with Hot Tub

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Work, play & winter in Woodstock! In-town with hot tub.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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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Magical Chalet with spectacular views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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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Private Home, Mins. to Woodstock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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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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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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Absolutely Gorgeous 1876 Eyebrow Colonial Home on 36 acres. Kids under 12 free!

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Brookside Retreat: Streamside Patio, Fireplace, Writer's Studio, Walk to Villag

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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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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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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Stunning home with pool, spa, mountain views, sleeps up to 12, walk to Woodstock

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Gracious Woodstock Retreat -Walking Distance to Town

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Privacy & Luxury * Heart of Woodstock w/ Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Best of Both Worlds: Mtn Views, Fireplace, Pool, Walk to Village Green!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Custom Post and Beam Home on a Stream

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Woodstock-SUMMER Charming 2BR Cottage w/inground POOL on 10acres -mountain views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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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
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Contemporary, Secluded Cabin in the Heart of Woodstock W/ Hot Tub & Fireplace

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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 Cabin in Woodstock, NY- Cozy and Pet Friendly

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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House on 35 Acres w/Mt Views, Private Trails & Creeks

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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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Mountain Gardens - DOGS WELCOME!!!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet Friendly Cabin Doh-Ray up * 1500 ft

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family Rental - Log House & Renovated Modern Home in One, Heated Saltwater Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded, Luxury Home with Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mid-Century Gem with Heated Pool 1 Mile from Town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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MODERN house with a pool and hot tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Woodstock Mediterranean Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New Luxury 5BR Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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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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Margaret's Cottage New listing Woodstock Village

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Updated/Pet-Friendly Cabin By Hikes and Woodstock!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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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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