Zena Rentals
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This unusual house on the corner has a layout like no other house in Woodstock.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
3 1/2 bedrooms and 2 full bathrooms has been completely renovated. The kitchen has all brand new LG appliances. The LG ...
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Woodstock Cottage with a view !
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Offering a quaint and charming Woodstock artists cottage. Complete with mowed trails right off the front porch into 60 a ...
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Artists cottage on preserved land
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A very special Woodstock artists cottage that sits right on preserved land, with open views and big sky. Thorn Preser ...
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From $250 per night (USD)Expedia
Cozy and eclectic Woodstock getaway
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Recently renovated space with hand crafted touches, the Stardust Suite is a creative nook inspired by both our journey o ...
From $250 per night (USD)Expedia
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Family retreat with Guest House
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Set on 8 magical acres with a large swimming pool and huge deck that leads to a private pond, this property is a lovely ...
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From $259 per night (USD)VRBO
Red Maple Studio & Spa: Steam, Stream & Dream at Sawkill in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 2.5 miles from the heart of Woodstock and 10 minutes to uptown Kingston! Enjoy our custom-designed 400 sq ft studi ...
From $259 per night (USD)VRBO
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New Beautiful Private High-End Catskills Home with Heated Gunite Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This brand new home is the perfect Catskills getaway. Large windows & vaulted ceilings bring the outside in. With a stun ...
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From $499 per night (USD)VRBO
NEW! Woodstock-Private-Exquisite-Modern A-Frame-Minimum Stays are Monthly!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Style meets convenience for a relaxing and peaceful stay. Plan your MONTH-LONG visit to the Hudson Valley and use Wood ...
From $499 per night (USD)VRBO
From $374 per night (USD)VRBO
Family Oasis - Minutes from Hiking & Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Town of Woodstock Special Use (aka STR) Permit #23-0683 Featured in Hudson Valley Style Magazine, this fully renovated ...
From $374 per night (USD)VRBO
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Chestnut Hill Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ecently renovated artist studio located in Woodstock, the Country's Most Famous Small Town in America! Everything is bra ...
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Woodstock Luxury Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
BRAND NEW / Completely Renovated 3 Bedroom (2 Queen Beds & 2.5 Bath w bidets). For May - $5000/month For June-October - ...
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From $150 per night (USD)VRBO
Beautiful cottage with HOT TUB in Kingston\/Woodstock Catskills, Hudson Valley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
I offer you our Guest house which sits on a wooded dead end street in the Town of Woodstock. Close to Kingston, minutes ...
From $150 per night (USD)VRBO
From $407 per night (USD)VRBO
Beautiful & Spacious Woodstock Home w\/ Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This peaceful home is 4 miles from Tinker St, offers two acres of serene woodlands, a fire pit, pool & porch for bird wa ...
From $407 per night (USD)VRBO
From $198 per night (USD)VRBO
Frolic & Focus in this Bright Stylish Woodstock Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This bright stylish guest house is 5 minutes from fresh croissants in downtown Woodstock and 10 minutes from the gloriou ...
From $198 per night (USD)VRBO
From $325 per night (USD)VRBO
Stunning Historic Church
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
"The Little Church on the HIll." Find your refreshing and peaceful retreat away at a stunning church transformed into c ...
From $325 per night (USD)VRBO
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Newly built Modern Cabin walk to town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroo ...
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From $116 per night (USD)VRBO
Private apartment suite, dedicated WiFi, easy access to Woodstock village
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private apartment in a country setting, 1 mile from town center, along popular walking and bicycling road. Near restaura ...
From $116 per night (USD)VRBO
From $410 per night (USD)Expedia
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Brookside Retreat is ideally located on a quiet side street overlooking Tannery Brook, a year-round stream that flows th ...
From $410 per night (USD)Expedia
From $778 per night (USD)VRBO
The 212 Escape - Main House
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Amazing amenities include: - 5 person sauna (so relaxing you won’t want to leave) - Cal spa hot tub (available all year ...
From $778 per night (USD)VRBO
From $170 per night (USD)VRBO
Welcome Fall\/Winter with a Private Woodstock Glamping Experience!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come back to Nature...Come back to yourself! The Nest at Woodstock is the most unique private Glamping site in the Huds ...
From $170 per night (USD)VRBO
From $290 per night (USD)VRBO
Woodstock Paradise with Gardens & Private Heated Pool (seasonal)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
COME VISIT OUR COZY HOME WITH BEAUTIFUL FIREPLACE. LOVELY PRIVATE POOL, HOUSE & GARDEN IN SEASON. Our charming, cozy a ...
From $290 per night (USD)VRBO
From $125 per night (USD)Expedia
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a charming 'Camping Cabin' in the woods on more than 23 acres of woodlands overlooking a 1 1/2 acre lake. [Some ...
From $125 per night (USD)Expedia
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Cozy and spacious apartment in tree-lined neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We offer a complete garden apartment with a separate entrance on the first level of our family home. The floor plan of t ...
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From $252 per night (USD)Expedia
'Casa Reál' ~ Expansive Woodstock House w\/ Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 'Casa Reál,' an exquisite 4-bedroom, 4-bathroom ranch vacation rental in the iconic upstate town of Woodstock ...
From $252 per night (USD)Expedia
From $246 per night (USD)VRBO
Charming Cottage w\/ Yard - 2 Mi to Tinker St!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Take a break from the chaos of city life and head to the quaint village of Woodstock, where this cozy vacation rental aw ...
From $246 per night (USD)VRBO
From $360 per night (USD)Expedia
Bright, historic Woodstock home close to town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our historic Woodstock home is close to everything, but far enough away to be surrounded by trees, grass and peace & qui ...
From $360 per night (USD)Expedia
From $99 per night (USD)VRBO
Hotel Woodstock - Starflower 2D Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Overlooking the Woodstock village center, this antique hotel has 148 years of history and charm. From the front steps yo ...
From $99 per night (USD)VRBO
From $112 per night (USD)Expedia
Cottage - Wildflower Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
The Wildflower Suite is a Private Apartment in the #9 Blue Cottage at the back of the property. The suite is the 2nd flo ...
From $112 per night (USD)Expedia
From $415 per night (USD)VRBO
LARGE COZY Sleeps 7 Main House + Opt. Apt 4 More (+Fee) Pool\/Pond!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
“Classically American” in its design, this family home in Woodstock is very flexible. The main house has 4 bedrooms and ...
From $415 per night (USD)VRBO
From $350 per night (USD)Expedia
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A Broadway music director purchased this Woodstock home in 2015, and since then it's become the favorite getaway for man ...
From $350 per night (USD)Expedia
From $773 per night (USD)VRBO
Heated pool, outdoor deck, fire pit, basketball court, fireplaces, central air.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The pool is open from May 22, 2024 until October 7, 2024. We supply 50 gallons of gas for the pool heater weekly; guests ...
From $773 per night (USD)VRBO
From $514 per night (USD)VRBO
Cottonwood-A Luxury Woodstock Home Located Between Woodstock + Saugerties
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Cottonwood! An upscale 3 bedroom, private office/convertible bedroom, 2 bath, in a lovely, newly renovated sp ...
From $514 per night (USD)VRBO
From $255 per night (USD)VRBO
Our Heart of Woodstock Village Cottage, fully restored
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Just listed: Our lovely Woodstock cottage is the only fully private single family residence in the heart of the village. ...
From $255 per night (USD)VRBO
From $425 per night (USD)VRBO
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
WALK TO EVERYTHING IN THE VILLAGE FROM THIS COTTAGE WITH GORGEOUS VIEWS! Located in the center of the village, this ...
From $425 per night (USD)VRBO
From $204 per night (USD)VRBO
Streamside Cottage Walking Distance to Town of Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our stream side cottage is privately located on five park-like acres that are landscaped with beautiful gardens. Guests ...
From $204 per night (USD)VRBO
From $391 per night (USD)VRBO
Woodstock Nature's Chateau...so close to Saugerties, Kingston, Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Re-connect with nature. Located on a semi-private road, conveniently located just 3 miles to the village of Woodstock. ...
From $391 per night (USD)VRBO
From $797 per night (USD)VRBO
Hudson Valley Evergreen Treehouse
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our brand new Scandinavian designed 5 bedroom, 3 bath treehouse in the Woodstock Hudson Valley area. Experien ...
From $797 per night (USD)VRBO
From $322 per night (USD)VRBO
Serene Woodstock 3 bedroom cottage with sweeping mountain views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Recently built 3 bedroom/2 bath house with mountain views on 5 beautiful secluded acres surrounded by trees, a quick 3 m ...
From $322 per night (USD)VRBO
From $279 per night (USD)VRBO
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 1920 Woodstock cottage is a five-minute walk to the center of Woodstock and the Trailways bus stop and an equal dis ...
From $279 per night (USD)VRBO
From $360 per night (USD)VRBO
Woodstock Sanctuary Spa Retreat - walk to town!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Mountain Views | Cedar Hot Tub & Cold Plunge | Wood Stove | Walk to Town | Private Surrounded by towering pines and mou ...
From $360 per night (USD)VRBO
From $466 per night (USD)VRBO
Gracious Woodstock Retreat -Walking Distance to Town
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Elegant yet comfortable home in a rural wooded setting on 2 private acres, and only a 10 minute walk from town. King Be ...
From $466 per night (USD)VRBO
From $375 per night (USD)Expedia
JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Treat yourself to a romantic getaway or relaxing retreat in your own newly-renovated historic farmhouse, ideally located ...
From $375 per night (USD)Expedia
From $416 per night (USD)VRBO
Spacious, Private, Close to Town, Work From Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious, modern ranch-style house on 1.9 acres, atop a hill, with plenty of natural sunlight. Designed and decorated fo ...
From $416 per night (USD)VRBO
From $195 per night (USD)VRBO
Village Center: Gracious & Spacious Retreat \"Above the Books\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Treat yourself to a luxurious and inspiring getaway "Above the Books", just up the stairs from Woodstock’s legendary MIR ...
From $195 per night (USD)VRBO
From $2200 per night (USD)VRBO
Walk To Woodstock, Streamside W\/In Ground Pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Stunning country home with all the modern amenities & interior design you would want to have during your stay. Enjoy th ...
From $2200 per night (USD)VRBO
From $775 per night (USD)VRBO
Peaceful, stunning property 3 min to Woodstock-truly a \"Blissful Getaway\"
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Perfectly located, this spectacular home is a 2-minute drive or a 10-minute walk into the heart of our town – Woodstock’ ...
From $775 per night (USD)VRBO
From $1616 per night (USD)VRBO
Modern Glass House, Minutes to Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to one of the most beautiful homes in upstate New York. Perched on the edge of a ravine with huge windows, mult ...
From $1616 per night (USD)VRBO
From $288 per night (USD)Expedia
Private Home ~ All Yours ~ Newly Renovated ~ In Woodstock ~Walk everywhere~Quiet
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
House is cleaned with bleach solution as per CDC recommendations. While weekends are popular we offer larger discounts ...
From $288 per night (USD)Expedia
From $425 per night (USD)VRBO
Fabulous Newly Renovated Family House Near Woodstock Center
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Airy and comfortable, this newly-decorated Woodstock home promises a warm and relaxing vacation. Throw some logs onto th ...
From $425 per night (USD)VRBO
From $250 per night (USD)VRBO
Private Home, Mins. to Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
If you are looking for a place to get away, relax, be secluded from the hustle/bustle...this is the place! Take the pri ...
From $250 per night (USD)VRBO
From $850 per night (USD)VRBO
Special Summer Offer: Private Central Woodstock w\/ Heated Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
For Summer 2024 only: This is a unique opportunity to stay within walking distance to the center of Woodstock (less than ...
From $850 per night (USD)VRBO
From $85 per night (USD)Expedia
Studio close to Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 2
Fully furnished 750 square foot studio apartment with queen size bed, kitchen and one bathroom with shower, air conditio ...
From $85 per night (USD)Expedia
From $239 per night (USD)VRBO
Cozy Woodstock Home w\/ Fire Pit!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Plan your next getaway with your loved ones to this charming Catskills retreat in Woodstock New York! Located near Tinke ...
From $239 per night (USD)VRBO
From $573 per night (USD)VRBO
Woodstock\/Saugerties Retreat- Pool\/Hot Tub\/FirePit
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to The Evergreen, our Hudson Valley retreat located just 5 minutes from Woodstock village. Sitting on 3 acres am ...
From $573 per night (USD)VRBO
From $275 per night (USD)VRBO
Modern House In The Woods, Yet Close To Downtown Woodstock
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 6
This is a three bedroom modern home sitting on a small hill. The location is perfect, private yet convenient. It is walk ...
From $275 per night (USD)VRBO
From $373 per night (USD)Expedia
Romantic Luxury Chalet With Private Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dear Traveler, Look no further. This quiet, private and very romantic chalet exudes character, luxury and charm. P ...
From $373 per night (USD)Expedia
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Spa Cabin Close to Woodstock Center with Full Service Options
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Sounds of nature at all times. You can hear water falls, birds, occasionally the owl. Here you get to stay in comfort, n ...
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From $789 per night (USD)Expedia
The 212 Escape
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Amazing amenities include: - 5 person sauna (so relaxing you won’t want to leave) - Cal spa hot tub (available all year ...
From $789 per night (USD)Expedia
From $165 per night (USD)VRBO
Mountain view, mid-century style, 1 mile to town. New Listing 4.9 on other sites
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spacious Mountain Studio, mid-century style, on 4 acres. Wake up to a gorgeous view of the Catskill Mountains, seen thro ...
From $165 per night (USD)VRBO
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Zen Retreat in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a sanctuary for the ones who search for inner peace. It's right in the center of Woodstock but hiding seclusivel ...
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From $1299 per night (USD)VRBO
Woodstock Oasis 3 br 3 bath pool, monthly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A designer dream home. Rented month to month. 10 min walk to the town center This house is like no other. Centrally loca ...
From $1299 per night (USD)VRBO
From $296 per night (USD)Expedia
Charming Getaway in Woodstock\/ w hot tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Forget your worries and spend some quality time with friends and family on a spacious and serene property. Enjoy your ti ...
From $296 per night (USD)Expedia
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NEW! The Joyful Cabin - Modern Upstate Cabin Vibe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our joyful cabin is nestled on 6 wooded acres - this is the perfect place to rest and recharge. Soak in the sights in th ...
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From $304 per night (USD)Expedia
Woodstock Getaway w\/ Hot Tub ~ 2 Mi to Dtwn!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Visit renowned music venues, chase waterfalls, and enjoy the natural beauty of the Catskills when you stay at this all-s ...
From $304 per night (USD)Expedia
From $255 per night (USD)VRBO
Woodstock retreat w\/hot tub, 5 min from Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Peaceful, cozy country house, prime location, private deck with hot tub and proximity to the towns of Woodstock and Saug ...
From $255 per night (USD)VRBO
From $348 per night (USD)Expedia
Quaint Woodstock Escape - 2 Mi to Tinker St!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlighted by its spacious grounds and close proximity to restaurants, entertainment, and shopping, this secluded Woods ...
From $348 per night (USD)Expedia
From $526 per night (USD)VRBO
Secluded Mid-Century Fall Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience this Fall in your own secluded Mid-Century forest home yet only be five minutes from historically fabulous Wo ...
From $526 per night (USD)VRBO
From $375 per night (USD)VRBO
Modern Cottage w\/ Amazing Views & Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Modern 2 Bedroom Cottage with Stunning Mountain Views & Open Forest surroundings, with 200 Acres of Conservation Land. V ...
From $375 per night (USD)VRBO
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Seasonal rental one mile to Woodstock, near skiing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take it easy at this unique and tranquil getaway. If relaxation is what you are looking for then this is your place. Min ...
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Click For PricingVRBO
Savor Dreamy Treetop Views Under Whitewashed Beams
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Escape to your private, treetop hideout right in the village of Woodstock. Peaceful & private, this upper unit has an ea ...
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Click For PricingVRBO
Explore Woodstock from an Exceptional Home
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Sit by the fire in a living room with hardwood floors, relaxed furnishings, and distressed wood accents. Have a cookout ...
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Click For PricingVRBO
Woodstock getaway
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
A quaint house on a peaceful street just a 5-minute drive from downtown Woodstock and short walk to the Ashokan River Tr ...
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From $135 per night (USD)VRBO
Woodstock Country Guest Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Warm and inviting guest suite with private driveway and entrance in an extremely quiet neighborhood, around the corner f ...
From $135 per night (USD)VRBO
From $395 per night (USD)VRBO
\"Blissful Retreat\" Elegant , Charming & Peaceful
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Permit # 20H-095 Brand new, stylish, elegant, 1 bedroom apartment with office above a garage, located on 10.5 acres and ...
From $395 per night (USD)VRBO