11 Best Airbnb Vacation Rentals In Woodstock, New York - Updated 2022

Maria Cristina
Maria Cristina 

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 Airbnbs in Woodstock, New York while in town. Read our recommendations below.

1. Restored farmhouse with yoga studio (from USD 371)

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. Often called the best Airbnb in Woodstock, it is 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 Studio
Woodstock, New York, United States
447 reviews Superhost  Wifi Available
Entire cabin 3 Beds 8 Guests 3 Bedrooms 1 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the kitchen is functional and offers all the amenities that one would require when entertaining
yoga room was amazing and we ran a session at 8am saturday
the space was beautiful and extremely comfortable sleeping situation
clean and well appointed
it was clean and stocked with necessities
the communication was smooth and the house was clean basically had everything you need
the beds were so comfortable and everything was clean and neat
well stocked and clean
great host and wonderful stay
zach was the perfect host
he was a very gracious host
zack was an amazing host was very kind and patient with our scchedule
zack's a responsive and helpful host
the location is beautiful
great location just minutes from downtown
super close to downtown (5 minute drive)
wonderful location and beautiful stylish spaces
it is the perfect location from the town and from many trails in the area
Read more reviews

2. Bohemian hideaway best for couples (from USD 250)

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 Hideaway
213 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
living room with amenities large bathroom with lovely shower/tub
the netflix account on the tv was a nice touch for us
space was extremely comfortable and peaceful
it’s a comfortable space if you want to stay in with some take out and netflix
i especially enjoyed the well appointed comfy bed after a full day of skiing
everything was clean and well organized
very clean place private and quiet
benjamin 's place was very clean and spacious
super clean & easy check in
super clean and extremely cute
benjamin was a gracious host
ben was very helpful for diverse requests
thanks ben you certainly live up to your "super host" title
benjamin is very friendly helpful and was a great host
benjamin was very responsive every time
great location and very comfortable
this is a cute apartment in a great location
great location and comfortable space
comfortable space in a convenient location to downtown
great location close to woodstock and saugerties
Read more reviews

3. Charming bungalow with skylights (from USD 140)

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 Woodstock
Woodstock, New York, United States
610 reviews Superhost  Wifi Available
Entire cottage 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
beautiful sunny large room with skylights that look up our of the trees
the cottage is very warm and cozy and gives you the comfortable feeling of "home"
the space was clean and well maintained
this is a clean and convenient cottage
it was very clean and spacious highly recommend
marta was very accommodating with clean sheets towels and even a fresh baked muffin when we arrived
the space is very cozy clean and comfortable
marta was a kind host giving us clear check in info before arrival
you can tell marta enjoys being a welcoming host
marta is a wonderful host
marta is a great host and responded quickly to ant of our needs
the restaurant guide marta left for us was very helpful and informative
great location within quick walking distance from woodstock's main strip
great location in town
location is very central easy walk to most places
the location is perfect walking distance to all the shops and restaurants
the location of this little place was perfect
Read more reviews

4. Tastefully decorated carriage house best for families (from USD 286)

Those searching for charming houses for rent in Woodstock will find this rental to be a very suitable option. It 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 House
Woodstock, New York, United States
380 reviews Superhost  Wifi Available
Entire home 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the furniture and linen is super comfortable
the air conditioning worked great which we we’re grateful for
the cottage is cozy and comfortable
the cottage is beautifully designed serine and cozy
the cottage is cozy unique and very well equipped
the house was truly lovely and very clean my daughters and i had never been to woodstock
everything was clean and the kitchen was well suited for our needs
nin’s place was absolutely amazing private quiet clean comfy and cozy
as pictured great clean comfortable space with lots of helpful tips and details provided
the kitchen was pretty clean except for the rice grains i found around the stove
nin is a great host
nin was an amazing host
they were very friendly and helpful
friendly host and cozy well decorated space
nin was extremely responsive to our questions
location wise its great
amazing location with the creek and a public park steps away
the location is ideal to get to other towns nearby too
it is a wonderful location next to a river
easy process good price beautiful location and cute little cabin
Read more reviews

5. Stylish cabin with wildlife views (from USD 156)

If you’re looking for Woodstock cabin rentals, then this listing might interest you. 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 Town
Woodstock, New York, United States
269 reviews Superhost  Wifi Available
Entire place 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
queen sleeper sofa mattress was comfortable
the couch bed is actually firm and very comfortable
the pull-out couch was large and felt like a normal bed
we had fun cooking in the well-stocked kitchen and the deck space was incredibly peaceful
very slow wifi but great for digital detox
very clean and quiet
everything was clean cozy and comfortable
it was clean comfortable and cozy
the place was spotless comfortable and quiet
the place was perfect clean and quiet
susan was a wonderful host
susan was a great host
beautiful property and excellent host
susan is a superb host
susan is a gracious host
a charming cabin very close to a wonderful town
very close to town yet you feel like you are miles away from civilization
i really liked the location of the cabin it was the perfect distance away from town
it was close to everything and was an ideal spot for our visit
great location and clear instructions for the house
Read more reviews

6. Pet-friendly studio with outdoor fire pit (from USD 136)

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 Only
Woodstock, New York, United States
710 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
had a nice sized bathroom shower closet and kitchenette
room had some serious style and was cozy and comfortable
the bed was super comfortable
the space was very cozy and charming
such a great experience it was cozy and had that 70's feel
very clean and comfortable
the inside was very clean and well kept
we didn’t need fancy just clean and comfortable
loved the atmosphere so cool and clean
we felt like family very cool clean comfortable space for a relaxing getaway
the hosts are great
the hosts were wonderful people
they were very communicative friendly and gracious host
hosts are always friendly
great space and great hosts
the location is great
super cute and great location
great location within the town
the location is perfect; set back but close to town
great location just a short walk to town but very quiet
Read more reviews

7. Lovely boho apartment (from USD 129)

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.

Woodstock, New York, United States
565 reviews Superhost  Wifi Available
Entire guesthouse 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
extremely comfortable beds w lovely bedding
thanks to erin and martin for providing coffee in the apartment really made our morning wake-ups enjoyable
the furniture was comfortable stylish and really added to the vibe of the place
the day bed was also super comfy
the bed and kitchen are good
the house is nice and clean
thoughtful aesthetic and very clean
martin and erin's guest house was clean and beautifully decorated
we enyoyed the retro kitchen space and the big clean fridge for our snacks and beverages
walking distance to all things woodstock great communication and clean space
the host is nice
martin and erin are knowledgeable and lovely local hosts
martin and erin are great hosts
martin was very nice and was a great host
martin was super helpful we thoroughly enjoyed our stay
location is perfect walking distance to the town center
the location is perfect
great location that is within walking distance from the center of woodstock
place is centrally located rustic but very cute
great location - easy walk into town
Read more reviews

8. Classic artist’s house (from USD 231)

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 House
Woodstock, New York, United States
524 reviews Superhost  Wifi Available
Entire home 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the space is lovely and incredibly light-filled plus a very well stocked kitchen
just wish the kitchen had been better stocked with tea coffee butter etc
every room has a spectacular view of the beautiful woods that surround the house
comfy beds and plenty of natural light
oh and the king sized bed is super comfy
it was very clean and well stocked too
modern decor and very clean
everything was super clean modern and beautifully decorated
it was clean cozy and full of character
really lovely house clean cozy and perfectly appointed
the hosts were responsive and friendly
robert was a great host and we will definitely be returning to his lovely home again
robert was a great host very responsive and easygoing
robert was easy to reach and was very responsive to any problems we ran into
great location in terms of proximity to woodstock
super convenient location in woodstock
beautiful house and a great location
there are also many breathtaking hikes close by
great house in an awesome location
Read more reviews

9. Romantic retreat with nature views (from USD 128)

Suitable for couples looking for a romantic getaway home or solo travelers searching for a peaceful retreat, this quaint cottage in Woodstock can house two guests. Conceptualized by an artist, this cottage has a comfy queen-size bed, a fireplace, a bright dining area, a welcoming sitting area, an elegant bathroom, a full kitchen, an antique writing desk, a skylight, and more. Outside, you can sit on the patio by the stream or admire the lovely views of nature. The village center is a short walk away from this cottage.

Dutch Touch Woodstock Cottage
Woodstock, New York, United States
529 reviews Superhost  Wifi Available
Entire home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the cottage is so homey and comfortable
beautiful cottage cozy comfortable nice touches
the dutch touch cottage is a lovely cozy place conveniently located with wifi and a fireplace
the cottage is private stylish and most importantly comfortable
the cottage was everything we had hoped for - cozy quiet great location
a comfortable bed and cozy atmosphere clean beautiful fireplace
everything was very clean and the inside gives you that true country feel
the cabin was clean and all instructions were clear and convenient
clean loving and warm space to regroup on your own or in our case with someone you love
the cottage is sparkling clean and has everything you could need
the hosts were kind and warm
thank you so much to our hosts martine and kevin
the hosts were extremely friendly and accommodating
martine and kevin were great hosts
:)martine is a great host that responds quickly as well
the location was perfect
just a short walk to town it’s perfectly situated
the location is amazing just a short walk to the main strip in woodstock
walking distance from the picturesque town
just a few minutes from town the location is ideal
Read more reviews

10. Romantic cottage near a stream

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 Town
Woodstock, New York, United States
105 reviews
Entire cottage 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the bed is extremely comfortable and the portable ac unit was a nice touch
felt as if i was outside the air conditioning in the bedroom worked great on very warm evenings
the bathroom also was perfect
i love the fact that everywhere you say outside was so comfortable
book with confidence of a comfortable stay
the house is incredibly clean with everything you would need
all bed linens were clean and provided
fantastic location in this charming and clean house
and lisa was super responsive easy check in and super clean
beautiful clean close to town the cottage is so charming
linda was an excellent host
linda and gene were awesome hosts
linda and gene were perfect hosts highly recommend
linda and gene were so hospitable and made us feel very welcome
the hosts are quick to respond and provided us with everything needed for a great stay
wonderful location within walking distance to town
great location to walk to town
a truly perfect location
great place very close to the town
so relaxing and close to town
Read more reviews

11. Cozy cottage with mountain views

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 St
Woodstock, New York, United States
423 reviews
Entire cottage 2 Beds 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the cottage was comfortable with sweet extra touches such as flowers fruits coffee a welcome note etc
we loved the skylights that allowed us to see the moon from the bed at night
i stayed during a record breaking heat wave and cottage was cool and comfortable
it was clean and cozy with great ac for the hot/humid evenings
the bathroom and kitchen were clean and functional private deck area was nice for lounging outside
very clean and full of character
it was clean and very comfortable
the place is clean and cozy
it was very clean and the bed was comfortable
the place was clean and stylish
she is clearly an experienced host who enjoys hospitality
v the host was kind enough to allow us to check in early
the host was extremely helpful with finding local activities
v is a great host would book again
hosts were very accommodating and it was a wonderful experience
cute little place close to woodstock
peaceful yet close to the village
location was perfect
the location was great
beautiful location nestled away but still conveniently near the downtown area
Read more reviews

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. A wide range of vacation rentals in Woodstock are available to you, so don’t forget to include them in your travel plans.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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