Woodstock Rentals
From $516 per night (USD)VRBO
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 $516 per night (USD)VRBO
From $352 per night (USD)Expedia
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Brook Cottage Too is ideally located on a shared and secluded property at the end of a private lane, yet it’s just a few ...
From $352 per night (USD)Expedia
From $337 per night (USD)VRBO
Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our cozy art-filled home is nestled in the Woodstock forest with an acre of perennial gardens and private swimming pool. ...
From $337 per night (USD)VRBO
From $185 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 $185 per night (USD)Expedia
From $218 per night (USD)VRBO
Well-lit apartment. Overlook fields & woods. Near music, dining, cafes, hiking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to the heart of the Catskills in this charming 1-bedroom apartment in Woodstock. Nestled just a short drive from ...
From $218 per night (USD)VRBO
From $308 per night (USD)Expedia
Woodstock Historic Artist Estate - The Carriage House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped ...
From $308 per night (USD)Expedia
From $821 per night (USD)VRBO
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Picture yourself in an Arts-and-Crafts-style home, on 3.3 acres, just a short walk from Woodstock’s Village Green. We've ...
From $821 per night (USD)VRBO
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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 ...
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From $494 per night (USD)VRBO
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Creek Cottage was built in 1939. A charming 2 bedroom, 2 bath home that has been updated with the aim of keeping the or ...
From $494 per night (USD)VRBO
From $637 per night (USD)Expedia
Woodstock Historic Artist Estate - The Museum House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
The property is located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 25 ...
From $637 per night (USD)Expedia
From $601 per night (USD)VRBO
Bright, historic Woodstock home close to town
- Bedrooms:
- 1
- 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 $601 per night (USD)VRBO
From $429 per night (USD)Expedia
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brook Cottage is ideally located on a shared and secluded property at the end of a private lane, yet it’s just a few blo ...
From $429 per night (USD)Expedia
From $203 per night (USD)VRBO
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome To Your Colorful Modern Hideaway In The Heart Of Downtown Woodstock Part of a fully renovated property, this br ...
From $203 per night (USD)VRBO
From $668 per night (USD)VRBO
Woodstock Secluded Close to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
About this space: Our beautiful family vacation home is a 1/2 mile to town and sits on a 3 acre parcel with a stunning M ...
From $668 per night (USD)VRBO
From $218 per night (USD)VRBO
Beautiful Top Floor Unit in Downtown Woodstock!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience Woodstock from this top-floor apartment styled in timeless mid-century modern design. Clean lines, warm earth ...
From $218 per night (USD)VRBO
From $206 per night (USD)Expedia
Botanical Studio Retreat in the Heart of Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Peaceful and stylish studio in the heart of Woodstock. This bright space features a cozy queen bed, vintage clawfoot tub ...
From $206 per night (USD)Expedia
From $551 per night (USD)VRBO
Woodstock Waterfall Hideaway · Walk To Tinker St!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Perched above Tannery Brook's waterfall in the heart of Woodstock! This hideaway offers something hard to find: natural ...
From $551 per night (USD)VRBO
From $336 per night (USD)Expedia
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your Woodstock adventure begins at this wonderful 1-bedroom fully renovated cottage! A short walk to downtown Woodstock, ...
From $336 per night (USD)Expedia
From $857 per night (USD)VRBO
NEW: Architect-designed historic CARRIAGE HOUSE w/heated pool, AC, walk to town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A long-standing guest favorite, the Carriage House has recently reopened after a period of private occupancy. Thoughtfu ...
From $857 per night (USD)VRBO
From $727 per night (USD)VRBO
Charming Quiet Family Friendly Home Close To Town
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to our woodland playhouse, a home away from home for relaxing and reconnection. It’s the perfect secluded family ...
From $727 per night (USD)VRBO
From $232 per night (USD)VRBO
Woodstock Boho Retreat Screened Porch • Monthly Summer Escape
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our warm and thoughtfully designed Woodstock retreat — a peaceful Catskills escape created for longer stays, ...
From $232 per night (USD)VRBO
From $354 per night (USD)VRBO
Imagine Woodstock Byrdcliff House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Byrdcliffe House sits on the mountain side above Woodstock’s town square less than 1 mile away. The house is approa ...
From $354 per night (USD)VRBO
From $316 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 $316 per night (USD)VRBO
From $373 per night (USD)Expedia
Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Sled Hill House! A private retreat in the heart of Woodstock, NY—just a short walk to town and the Vill ...
From $373 per night (USD)Expedia
From $895 per night (USD)VRBO
Peaceful, stunning property 3 min to Woodstock-truly a \"Blissful Getaway\"
- Bedrooms:
- 2
- 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 $895 per night (USD)VRBO
From $564 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 $564 per night (USD)VRBO
From $273 per night (USD)VRBO
LIVE IN NATURE - WALK TO TOWN- CHILDREN LOVE US- SIT BY THE CAMP FIRE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
The Pike Lane Cabin is nestled in the woods situated on seven acres of quiet natural beauty yet minutes waking distance ...
From $273 per night (USD)VRBO
From $720 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 $720 per night (USD)VRBO
From $372 per night (USD)VRBO
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $372 per night (USD)VRBO
From $342 per night (USD)Expedia
Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the essence of Woodstock in this former home to Anita M. Smith — artist, historian and “Herb Lady of the Cats ...
From $342 per night (USD)Expedia
From $828 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 $828 per night (USD)VRBO
From $576 per night (USD)VRBO
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views
- Bedrooms:
- 2
- 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 $576 per night (USD)VRBO
From $305 per night (USD)VRBO
Streamside Cottage Half Mile 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 $305 per night (USD)VRBO
From $455 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 $455 per night (USD)VRBO
From $504 per night (USD)VRBO
Maple House: Private/Romantic Walk-to-Town Oasis
- 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 $504 per night (USD)VRBO
From $291 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 $291 per night (USD)VRBO
From $2832 per night (USD)VRBO
Walk To Woodstock, Streamside W/In Ground Pool
- Bedrooms:
- 5
- 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 $2832 per night (USD)VRBO
From $314 per night (USD)Expedia
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
..........The Teahouse Cottage is on an estate that was the home of Woodstock artist Judson Smith. He used the Teahous ...
From $314 per night (USD)Expedia
From $196 per night (USD)VRBO
Mid-Century Woodstock Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our mid-century Woodstock retreat! This one-level home features an open-concept layout that seamlessly blends ...
From $196 per night (USD)VRBO
From $253 per night (USD)Expedia
Renovated home seconds from town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this newly renovated Woodstock Home (3BR/2.5 BA/1,595 sq ft). A dream getaway for those looking to fall in l ...
From $253 per night (USD)Expedia
From $215 per night (USD)VRBO
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Groovy Getaway in Woodstock – Vinyl Vibes & Retro Style! Step back in time to a groovier era in this colorful, music-lo ...
From $215 per night (USD)VRBO
From $179 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 $179 per night (USD)VRBO
From $212 per night (USD)VRBO
Rock City Writer’s Studio: Historic•Nordic Sauna•Walk to town!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Treat yourself to a relaxing, rejuvenating, and inspiring retreat in your own private historic studio cottage in the hea ...
From $212 per night (USD)VRBO
From $291 per night (USD)Expedia
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You will be Catskillin' it in this newly remodeled, over 500 sq. ft., design-forward 1BR cottage, bright and snug with p ...
From $291 per night (USD)Expedia
From $316 per night (USD)VRBO
Mountain view, mid-century style, 1 mile to town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Spacious Mountain Studio, mid-century style, on 4 acres. Wake up to a gorgeous view of the Catskill Mountains, seen thro ...
From $316 per night (USD)VRBO
From $179 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 $179 per night (USD)VRBO
From $196 per night (USD)VRBO
Mid-Century Modern House Convenient to All that Woodstock has to Offer.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Marko Grove is a Mid-Century Modern Raised Ranch house on a large lot in Woodstock’s well-known Bearsville Flats neighbo ...
From $196 per night (USD)VRBO
From $344 per night (USD)VRBO
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a newly renovated apartment in and old studio. Close (1 mile) to the center of the village of Woodstock, NY. Wit ...
From $344 per night (USD)VRBO
From $268 per night (USD)VRBO
Adorable Red Cottage, walking distance to Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
We invite you to enjoy your time upstate in our Cozy Red Woodstock Cottage! This adorable, thoughtfully renovated 2 BR ...
From $268 per night (USD)VRBO
From $123 per night (USD)Expedia
Charming 1-bedroom cottage in Woodstock with AC, WiFi min Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Consider this cottage your home away from home while you visit Woodstock. This cozy retreat features 1 serene bedroom wi ...
From $123 per night (USD)Expedia
From $562 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 $562 per night (USD)VRBO
From $451 per night (USD)VRBO
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
<p>Location is everything! It is just a couple of miles from Woodstock village on a quiet dead-end road. Ashokan Reservo ...
From $451 per night (USD)VRBO
From $855 per night (USD)VRBO
Woodstock historic artist estate - The Pond House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This is an architect/artist home featured in various design magazines including Architectural Digest and Icon Design Mag ...
From $855 per night (USD)VRBO
From $812 per night (USD)Expedia
Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Experience Woodstock, NY and the Catskill Mountains while staying at our lovely four-bedroom home. Located on nearly thr ...
From $812 per night (USD)Expedia
From $419 per night (USD)VRBO
PVT RETREAT in Woodstock 4Br, Htd. Pool, Hot Tub, Min. to Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home in the Shady hamlet of Woodstock, less than 10 minutes from Town, is the perfect Retreat. There are 4 bedrooms ...
From $419 per night (USD)VRBO
From $1307 per night (USD)Expedia
Modern Farmhouse w/ Heated Pool & Creek Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to a beautifully restored farmhouse that blends timeless charm with modern comforts. Nestled in a peaceful, sceni ...
From $1307 per night (USD)Expedia
From $422 per night (USD)VRBO
CLASSIC WOODSTOCK Minutes to Town, Heated Pool, Pond, Views, AC, WiFi, Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A classic Woodstock home on 4 private acres just minutes from the center of town. Heated pool in summer, views all year ...
From $422 per night (USD)VRBO
From $398 per night (USD)Expedia
Chronogram featured, Modern Mountain Family Home above Woodstock. Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Featured in Chronogram Magazine as a modern eco-friendly mountain home with geo thermal heating and cooling and solar po ...
From $398 per night (USD)Expedia
From $366 per night (USD)VRBO
Pristine Woodstock Mountaintop Log Cabin — Only 4 Minutes to Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Treat yourself to a romantic getaway or family retreat in your own private log cabin on Ohayo Mountain, just 1.5 miles f ...
From $366 per night (USD)VRBO
From $449 per night (USD)Expedia
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 $449 per night (USD)Expedia
From $830 per night (USD)VRBO
Spacious & Magical 6-Bedroom Woodstock Getaway on Large Private Property
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Enjoy a magical stay at this 6-bedroom house in Woodstock. We just finished a big renovation, and the house is full of ...
From $830 per night (USD)VRBO
From $866 per night (USD)Expedia
Woodstock Ridge / Hot Tub, Pool & Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Woodstock Ridge is an exquisite escape designed for rejuvenation and luxury. This stunning property offers an exc ...
From $866 per night (USD)Expedia
From $440 per night (USD)VRBO
Peaceful Woodstock Retreat in the Catskills family friendly, spacious 6 bedroom
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
This Woodstock house boasts 6 inviting bedrooms, including 3 full beds, 1 queen, 3 twins, and a sofa bed. Guests enjoy 2 ...
From $440 per night (USD)VRBO
From $585 per night (USD)VRBO
Sweeping Mountain-View Cabin, Woodstock Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This 3-bedroom cabin is perfect for your escape to Woodstock. Guests will find two queen beds and a twin bed, plus a coz ...
From $585 per night (USD)VRBO
From $1101 per night (USD)VRBO
Woodstock Luxury Home- heated pool, hot tub, 9 beds
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
This home has been on that other place for 9+ years with over 100+ reviews :) Heated pool is open! I will work with you ...
From $1101 per night (USD)VRBO
From $603 per night (USD)VRBO
Absolute Woodstock Chill
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Catskills from the vision of a man who designed and built, with his bare hands, a home in harmony with it ...
From $603 per night (USD)VRBO
From $337 per night (USD)VRBO
Woodstock Mountaintop Country Compound w. Pool & Sauna on 10 Acres
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A newly-renovated home for your family just 4 minutes from Woodstock center! Surround yourself in nature in our Woodstoc ...
From $337 per night (USD)VRBO
From $1033 per night (USD)VRBO
Woodstock Colonial Estate w/ Pool, Hot Tub, Sauna
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Picture this: Saturday morning. The smell of espresso drifting from the coffee bar room. Your group scattered across fiv ...
From $1033 per night (USD)VRBO
From $753 per night (USD)VRBO
Woodstock walk to town, entire home and property to yourself, mountain views.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Broadview Retreat House is located in Woodstock NY. The house is a 10 minute walk to Tinker Street, the center of town. ...
From $753 per night (USD)VRBO
From $739 per night (USD)VRBO
Woodstock Mid-Century Gem Heated Pool Near Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A beautifully preserved 1960 mid-century modern stone-and-glass home in Woodstock, offering privacy, style, and an excep ...
From $739 per night (USD)VRBO
From $871 per night (USD)VRBO
Heated Saltwater Pool • 4 Min to Woodstock • Private Deck & Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The pool is open from May 25, 2026 through September 28, 2026. Private Woodstock Retreat with Heated Saltwater Pool – 4 ...
From $871 per night (USD)VRBO
From $392 per night (USD)VRBO
Charming 3 Bedroom Cabin with Mountain Views in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect mountain retreat! Nestled on 15 private acres, this whimsical rustic cabin offers a magical esca ...
From $392 per night (USD)VRBO
From $755 per night (USD)VRBO
Woodstock mountain cottage & pool, SWIM, hike, relax, secluded modern 2 br house
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We invite you to a serene, romantic cottage set on 10 private acres in the countryside—ideal for two couples or a small ...
From $755 per night (USD)VRBO
From $361 per night (USD)VRBO
Mid-Century Artist Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Catskills in our mid-century home located in this hamlet of Woodstock. Close to downtown to enjoy Woodsto ...
From $361 per night (USD)VRBO
From $456 per night (USD)VRBO
Pet Friendly Cabin Doh-Ray up @ 1500 ft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
3 -30 day minimum depending on season. Discount with 7 days. + Surrounded by the forests of Mt. Guardian at an altitude ...
From $456 per night (USD)VRBO
From $827 per night (USD)VRBO
Spacious Private Retreat w. Pool + Fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Down a private drive, this spacious Woodstock home sits on 3 acres in beautiful, private, natural surroundings. Featurin ...
From $827 per night (USD)VRBO
From $426 per night (USD)VRBO
The Mod Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Discover a cute Catskills hideaway: a warm, cozy and stylish vacation home perfectly located by the dow ...
From $426 per night (USD)VRBO
From $487 per night (USD)Expedia
Chic and eclectic retreat at Woodstock/Saugerties!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated old barn, circa 1810, with chic, modern and eclectic design, with landscaped lawn/garden. A wonder ...
From $487 per night (USD)Expedia
From $570 per night (USD)VRBO
Woodstock Artist's Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Relax, create, and enjoy the Woodstock Artist's Retreat. 6 serene acres hugged by magical Overlook Mountain, Lewis ...
From $570 per night (USD)VRBO
From $305 per night (USD)VRBO
Secluded 3BR w/ Private Pool & Epic Views – 10 Mins to Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Craving space, quiet, and fresh mountain air? This 3-bedroom cliffside retreat is your ideal upstate escape—just two hou ...
From $305 per night (USD)VRBO
From $427 per night (USD)VRBO
Woodstock Mtn Lodge- pvt 2 acres w/saline pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Magical upstate cottage on 2 acres in the heart of Woodstock. Pvt heated saline pool & beautifully landscaped gardens w/ ...
From $427 per night (USD)VRBO
From $377 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 $377 per night (USD)VRBO
From $163 per night (USD)VRBO
A Wonderful House. High on a hill overlooking the mountains and valleys.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
We want to rent only for the season, from November 15th until March 31st. We have a beautiful, light-filled modern hous ...
From $163 per night (USD)VRBO
From $433 per night (USD)VRBO
The CubHouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WOODSTOCK/BEARSVILLE Escape to a little healing magic in this 1909 built cottage. Originally owned by a medicine woman i ...
From $433 per night (USD)VRBO
From $428 per night (USD)VRBO
Unequalled Views of Reservoir & Mtns, Affordable, Totally Private
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
SKYLOFT, your own private piece of the world. Quiet, away from everything, yet not isolated.. SKYLOFT is a 1000-sq-ft ap ...
From $428 per night (USD)VRBO
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Woodstock/Entire house with pool 1.5 miles to Village Green. Very private.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stylish and comfortable private home just 1.5 miles from Village Green with private lawn, woods. In ground pool with pat ...
Click For PricingVRBO
From $577 per night (USD)VRBO
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
- Bedrooms:
- 2
- 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 $577 per night (USD)VRBO
From $396 per night (USD)VRBO
Saugerties-Woodstock retreat, hot tub, 5 min from Woodstock
- 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 $396 per night (USD)VRBO
From $680 per night (USD)VRBO
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 $680 per night (USD)VRBO
From $755 per night (USD)Expedia
Cozy Mid-Century Retreat with Spa Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Recently featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCent ...
From $755 per night (USD)Expedia
From $232 per night (USD)VRBO
Imagine The Woodstock House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Woodstock House is distinctive and gracious. The Woodstock house is ideally located within walking distance to the ...
From $232 per night (USD)VRBO
From $548 per night (USD)Expedia
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax and rejuvenate at this magical woodland cottage in Woodstock, New York. Tucked away in a tranquil setting yet only ...
From $548 per night (USD)Expedia
From $474 per night (USD)VRBO
Cozy Escape in Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Find complete country zen within walking distance of the village of Woodstock. This charming 3-bedroom has all ...
From $474 per night (USD)VRBO
From $351 per night (USD)Expedia
Private cottage - 5 min from the center of town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy the music, art, shopping and restaurants of Woodstock in the winter holiday season! Hike the many trails, explor ...
From $351 per night (USD)Expedia