The town of Woodstock is located in the northern part of Ulster County, in Kingston’s northwest, and along the borders of New York’s Catskill Mountains. Ironically, the iconic Woodstock rock concert in 1969 did not happen in this free-spirited mountain town. However, the persistent hippie spirit of the town created the festival’s concept and paved the way for the proliferation of various arts and music movements. Woodstock has been a thriving art colony since 1902, and to this day the town overflows with diversity – evident in their art institutes, live music scenes, and assorted shops. The surrounding majestic mountains offer relaxing, Zen-type outdoor activities. It’s not surprising, because at the peak of Mead’s Mountain road is the Buddhist monastery of Karma Triyana Dharmachakra. Visit this mecca for the artistic types, and book one of the best Airbnb vacation rentals in Woodstock, New York while in town. Read our recommendations below.
From outside, you won’t think that this old 1870s farmhouse had a modern upgrade. The white interiors kept the original exposed brick wall, fireplace, and wooden frames as accents. It’s decorated with colorful vintage and modern furniture. Enjoy watching Netflix on the projector screen with a high-class sound system in the living room. It shares the open layout with a fully stocked kitchen and dining area. There are three spacious air-conditioned bedrooms, each containing Queen beds and one-and-a-half bathrooms to host eight guests. The attic is a cozy yoga studio accessible by climbing a spiral staircase. Host barbeques and park for free on the lot outside. The house is near the Catskill Mountains, the Big Deep, and it’s a five-minute drive to downtown.
Restored Farmhouse with Yoga StudioWoodstock, New York, United States
Top guest reviewsthe kitchen is functional and offers all the amenities that one would require when entertainingyoga room was amazing and we ran a session at 8am saturdaythe space was beautiful and extremely comfortable sleeping situationclean and well appointedit was clean and stocked with necessitiesthe communication was smooth and the house was clean basically had everything you needthe beds were so comfortable and everything was clean and neatwell stocked and clean
Host:great host and wonderful stayzach was the perfect hosthe was a very gracious hostzack was an amazing host was very kind and patient with our scchedulezack's a responsive and helpful hostRead more reviewsthe location is beautifulgreat location just minutes from downtownsuper close to downtown (5 minute drive)wonderful location and beautiful stylish spacesit is the perfect location from the town and from many trails in the area
The Dreamcatcher Cottage is a cozy space for three guests. It’s walking distance to the town, and Tinker Street is less than a mile (1.6km) away. It’s a studio-type dwelling newly remodeled with cathedral ceilings, picture windows, skylights, and an open layout featuring a tiny country kitchen with a breakfast nook, a queen-sized bed, and a sofa bed. Comforts like a private bathroom, air-conditioning, ceiling fans, free Wi-Fi, free bath essentials, heating, baby equipment, hot water, and free parking are provided. The house has a tiny porch and a barbecue area with a beautiful view of Overlook Mountain. This accommodation is LGBTQ-friendly, and pets are welcome. Luggage drop-off and long-term stays are allowed.
Dreamcatcher Cottage | Mtn View, Mins to Tinker StWoodstock, New York, United States
Top guest reviewsthe cottage was comfortable with sweet extra touches such as flowers fruits coffee a welcome note etcwe loved the skylights that allowed us to see the moon from the bed at nighti stayed during a record breaking heat wave and cottage was cool and comfortableit was clean and cozy with great ac for the hot/humid eveningsthe bathroom and kitchen were clean and functional private deck area was nice for lounging outsidevery clean and full of characterit was clean and very comfortablethe place is clean and cozyit was very clean and the bed was comfortablethe place was clean and stylish
Host:she is clearly an experienced host who enjoys hospitalityv the host was kind enough to allow us to check in earlythe host was extremely helpful with finding local activitiesv is a great host would book againhosts were very accommodating and it was a wonderful experienceRead more reviewscute little place close to woodstockpeaceful yet close to the villagelocation was perfectthe location was greatbeautiful location nestled away but still conveniently near the downtown area
This genuine hand-built 1960s Bohemian home is built with wood and stone collected from a property near the town, in a wooded area filled with hiking trails. The exact location is revealed upon booking confirmation. This private accommodation is ideal for couples. It’s part of the owner’s main house, with a private stairway and side entrance. By the front door is a small terrace offering refreshing outdoor views. The modest interiors feature a simple but cozy living room, a tiny kitchenette, a bedroom with a thick cushioned queen bed, and a private bathroom with a soaking tub. Modern comforts like Wi-Fi, heating, cable TV, air-conditioning, hot water, and free parking are available.
Chestnut Hill HideawayWoodstock, New York, United States
Top guest reviewsliving room with amenities large bathroom with lovely shower/tubthe netflix account on the tv was a nice touch for usspace was extremely comfortable and peacefulit’s a comfortable space if you want to stay in with some take out and netflixi especially enjoyed the well appointed comfy bed after a full day of skiingeverything was clean and well organizedvery clean place private and quietbenjamin 's place was very clean and spacioussuper clean & easy check insuper clean and extremely cute
Host:benjamin was a gracious hostben was very helpful for diverse requeststhanks ben you certainly live up to your "super host" titlebenjamin is very friendly helpful and was a great hostbenjamin was very responsive every timeRead more reviewsgreat location and very comfortablethis is a cute apartment in a great locationgreat location and comfortable spacecomfortable space in a convenient location to downtowngreat location close to woodstock and saugerties
The façade of this cottage is bright yellow with navy blue roofing and surrounded by a lush garden. The bungalow has cathedral ceilings with skylights and a cozy ambiance for two. It has limited space and an open layout that contains a king-sized bed, a lounger, a tiny dining area for two, and a kitchenette complete with coffee making facilities. The private bathroom has its own enclosed shower. The accommodation is built right beside the owner’s main house. A few steps away is a vast field with distant mountain views. Down the street are bike rentals, a yoga studio, a bar, and an ice cream parlor.
THE YELLOW COTTAGE in the heart of WoodstockWoodstock, New York, United States
Top guest reviewsbeautiful sunny large room with skylights that look up our of the treesthe cottage is very warm and cozy and gives you the comfortable feeling of "home"the space was clean and well maintainedthis is a clean and convenient cottageit was very clean and spacious highly recommendmarta was very accommodating with clean sheets towels and even a fresh baked muffin when we arrivedthe space is very cozy clean and comfortable
Host:marta was a kind host giving us clear check in info before arrivalyou can tell marta enjoys being a welcoming hostmarta is a wonderful hostmarta is a great host and responded quickly to ant of our needsthe restaurant guide marta left for us was very helpful and informativeRead more reviewsgreat location within quick walking distance from woodstock's main stripgreat location in townlocation is very central easy walk to most placesthe location is perfect walking distance to all the shops and restaurantsthe location of this little place was perfect
This rental is a former carriage house built on an artist’s estate and surrounded by a pond and lush trees. It’s a space suitable for four guests, equipped with fashionable, European-style interiors and vaulted ceilings. The two spacious bedrooms have huge beds and expensive linens and share one bathroom with a soaking tub. The living room shares the open-plan space with the dining area and a fully stocked kitchen. The house is designed with big picture windows in every room so you can enjoy unobstructed views of the pond and mountain scenery. A door in the living room opens to the barbecue area and an outdoor day bed. A state-of-the-art sound system, cable TV, air-conditioning, Wi-Fi, and baby equipment are provided during your stay.
Woodstock Historic Artist Estate - The Carriage HouseWoodstock, New York, United States
Top guest reviewsthe furniture and linen is super comfortablethe air conditioning worked great which we we’re grateful forthe cottage is cozy and comfortablethe cottage is beautifully designed serine and cozythe cottage is cozy unique and very well equippedthe house was truly lovely and very clean my daughters and i had never been to woodstockeverything was clean and the kitchen was well suited for our needsnin’s place was absolutely amazing private quiet clean comfy and cozyas pictured great clean comfortable space with lots of helpful tips and details providedthe kitchen was pretty clean except for the rice grains i found around the stove
Host:nin is a great hostnin was an amazing hostthey were very friendly and helpfulfriendly host and cozy well decorated spacenin was extremely responsive to our questionsRead more reviewslocation wise its greatamazing location with the creek and a public park steps awaythe location is ideal to get to other towns nearby tooit is a wonderful location next to a rivereasy process good price beautiful location and cute little cabin
Three miles to town on a hilly area surrounded by wildlife and just a few minutes’ drive to nearby restaurants, cafes, theaters, and a Tibetan monastery is a lovely wooden cottage. This newly remodeled bungalow has a furnished front deck with wooden chairs where you can relax and view the woods. French doors open to stylish interiors featuring cathedral ceilings, walls made of rough-cut Barn wood, and an open-plan space shared by a living room, dining area, and country kitchen. There is no bedroom, but there is a bathroom with a tub and free essentials. To sleep two guests, there is a cozy sofa bed in the living room. The Wi-Fi signal tends to be intermittent but with beautiful natural surroundings waiting to be explored, who needs the internet?
Woodstock cabin 3 miles from townWoodstock, New York, United States
Top guest reviewsqueen sleeper sofa mattress was comfortablethe couch bed is actually firm and very comfortablethe pull-out couch was large and felt like a normal bedwe had fun cooking in the well-stocked kitchen and the deck space was incredibly peacefulvery slow wifi but great for digital detoxvery clean and quieteverything was clean cozy and comfortableit was clean comfortable and cozythe place was spotless comfortable and quietthe place was perfect clean and quiet
Host:susan was a wonderful hostsusan was a great hostbeautiful property and excellent hostsusan is a superb hostsusan is a gracious hostRead more reviewsa charming cabin very close to a wonderful townvery close to town yet you feel like you are miles away from civilizationi really liked the location of the cabin it was the perfect distance away from townit was close to everything and was an ideal spot for our visitgreat location and clear instructions for the house
This cute studio room is only one of many units in a remodeled 1920s carriage house. The Rocket Room is designed with 70s vintage and Bohemian décor and a spacious open plan. There’s a cozy double bed that sleeps two and a couch for relaxing and listening to music from the turntable or radio. The kitchenette is equipped to cook simple meals with a bar counter for dining-in. Enjoy hot showers with free essentials. Luxuries like air-conditioning, Wi-Fi, heating, beach essentials, TV, baby equipment, free parking, and luggage drop-off are provided. Pets are welcome without additional fees. Hangout at the backyard with an outdoor fire pit and a swing. Rent bikes to ride to the town, or walk to the nearby bar, ice cream parlor, theater, yoga studio, and restaurants.
Rocket Room - Rock Stars OnlyWoodstock, New York, United States
Top guest reviewshad a nice sized bathroom shower closet and kitchenetteroom had some serious style and was cozy and comfortablethe bed was super comfortablethe space was very cozy and charmingsuch a great experience it was cozy and had that 70's feelvery clean and comfortablethe inside was very clean and well keptwe didn’t need fancy just clean and comfortableloved the atmosphere so cool and cleanwe felt like family very cool clean comfortable space for a relaxing getaway
Host:the hosts are greatthe hosts were wonderful peoplethey were very communicative friendly and gracious hosthosts are always friendlygreat space and great hostsRead more reviewsthe location is greatsuper cute and great locationgreat location within the townthe location is perfect; set back but close to towngreat location just a short walk to town but very quiet
This stylish one-bedroom apartment is in a woody area bordering the Colony of the Arts, three minutes away from the public library, ice cream shop, Station Bar, Upstate Films, and Woodstock Pizza Theater. It’s ideal for three guests and a pet. The lovely interiors feature brightly colored walls, eclectic furniture, and Boho inspired home accents. It’s equipped with a spacious bedroom with a queen bed, a living room with a single day bed, a fully equipped kitchen, and a full bathroom. For entertainment, you have cable TV, free Wi-Fi for streaming and Netflix, a radio, and a vintage record player. Feel free to use the outdoor area to have a picnic or a barbecue. There’s space for kids to swing, play, and run around.
BOHEMIAN RHAPSODY - Be Here NowWoodstock, New York, United States
Top guest reviewsextremely comfortable beds w lovely beddingthanks to erin and martin for providing coffee in the apartment really made our morning wake-ups enjoyablethe furniture was comfortable stylish and really added to the vibe of the placethe day bed was also super comfythe bed and kitchen are goodthe house is nice and cleanthoughtful aesthetic and very cleanmartin and erin's guest house was clean and beautifully decoratedwe enyoyed the retro kitchen space and the big clean fridge for our snacks and beverageswalking distance to all things woodstock great communication and clean space
Host:the host is nicemartin and erin are knowledgeable and lovely local hostsmartin and erin are great hostsmartin was very nice and was a great hostmartin was super helpful we thoroughly enjoyed our stayRead more reviewslocation is perfect walking distance to the town centerthe location is perfectgreat location that is within walking distance from the center of woodstockplace is centrally located rustic but very cutegreat location - easy walk into town
In a secluded area in the forest near Bearsville is this classic cottage that was once an artist’s studio. It was remodeled to host five guests comfortably. It now has lots of seating areas, two bedrooms with unique motifs, a cozy den for TV viewing and watching movies, and a sunroom where you can hide away with a book or take naps. The vaulted ceilings, picture windows, skylights, and wooden interiors give the feel of a rustic country vibe. Cook gourmet meals in the chef’s kitchen and eat in the stylish dining room. Spend the rest of the day exploring the surrounding forest, keeping warm by the outdoor fire pit, or having a barbeque in the backyard. Soak in a relaxing hot water bath in the tub before sleeping on thick cushioned beds. Wi-Fi, cable TV, laundry facilities, heating, and free parking are provided.
Ophelia - Classic Woodstock Artist HouseWoodstock, New York, United States
Top guest reviewsthe space is lovely and incredibly light-filled plus a very well stocked kitchenjust wish the kitchen had been better stocked with tea coffee butter etcevery room has a spectacular view of the beautiful woods that surround the housecomfy beds and plenty of natural lightoh and the king sized bed is super comfyit was very clean and well stocked toomodern decor and very cleaneverything was super clean modern and beautifully decoratedit was clean cozy and full of characterreally lovely house clean cozy and perfectly appointed
Host:the hosts were responsive and friendlyrobert was a great host and we will definitely be returning to his lovely home againrobert was a great host very responsive and easygoingrobert was easy to reach and was very responsive to any problems we ran intoRead more reviewsgreat location in terms of proximity to woodstocksuper convenient location in woodstockbeautiful house and a great locationthere are also many breathtaking hikes close bygreat house in an awesome location
This tiny wooden cottage is perfect for an outing in the woods. It sits beside a stream and is walking distance to town. Enjoy its rustic country-style interiors of vaulted ceilings and hardwood flooring furnished with a mix of oriental and vintage home accents. The bedroom sleeps two guests in a comfy queen bed, and it’s decorated with a barn door, a chest of drawers, big windows with box seats, and French doors that open to a wide deck overlooking the stream. The old-fashioned bathroom features a copper sink with a wooden counter and a rainfall walk-in shower. The tiny but fully equipped kitchen has a dining area for two. The property is surrounded by a lush forest with a beautiful stone walkway around its perimeters. Relax on the pergola, or hang out in the garden by the firepit and grill barbecues or toast marshmallows.
Romantic Cottage on the Stream, Walk to TownWoodstock, New York, United States
Top guest reviewsthe bed is extremely comfortable and the portable ac unit was a nice touchfelt as if i was outside the air conditioning in the bedroom worked great on very warm eveningsthe bathroom also was perfecti love the fact that everywhere you say outside was so comfortablebook with confidence of a comfortable staythe house is incredibly clean with everything you would needall bed linens were clean and providedfantastic location in this charming and clean houseand lisa was super responsive easy check in and super cleanbeautiful clean close to town the cottage is so charming
Host:linda was an excellent hostlinda and gene were awesome hostslinda and gene were perfect hosts highly recommendlinda and gene were so hospitable and made us feel very welcomethe hosts are quick to respond and provided us with everything needed for a great stayRead more reviewswonderful location within walking distance to towngreat location to walk to towna truly perfect locationgreat place very close to the townso relaxing and close to town
The hippest homes in New York
The homes in this peaceful mountain town are as colorful, classy, and creative as its residents. The ambiance and amenities these accommodations provide make the most relaxing home-stays with a Bohemian touch. You have a wide range of vacation rentals to choose from, so don’t forget to include them in your travel plans when visiting Woodstock, New York.
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