Cottage vacation rentals in Woodstock

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Popular amenities for Woodstock cottage rentals

Cottage rentals with free parking

Superhost
A fire pit is surrounded by smooth stones and stacked firewood, creating a cozy outdoor area. Flames flicker upward, adding warmth to the serene backyard, which is framed by green foliage and grassy patches. A wooden deck is visible in the background.
Cottage in Phoenicia
4.9 out of 5 average rating, 213 reviews

Catskills Stream-side Home Hike & Relax

JakeRating, 5 stars1 month ago
Awesome stay! Great area, super clean house. Highly recommend!
Guest favorite
A functional kitchen features vibrant blue cabinetry and a wooden countertop island. Stainless steel appliances, including a gas stove and refrigerator, are included. Natural light illuminates the space through a window, highlighting the tiled flooring and organized cooking utensils.
Cottage in Willow
4.86 out of 5 average rating, 251 reviews

Peace Cottage

SarahRating, 5 stars3 months ago
I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.
Guest favorite
The kitchen features a large sink situated beneath a window with a view of the surrounding grove. A coffee maker and a dish drying rack are visible, along with fresh flowers on the windowsill and books on a nearby countertop.
Cottage in West Camp
4.93 out of 5 average rating, 123 reviews

Hudson Valley Cottage

AlexandraRating, 5 stars2 months ago
This was so charming & cozy, while also being conveniently close to nature nails & downtown Woodstock. We thoroughly enjoyed our stay & would recommend!
Top guest favorite
An open-concept space features wooden beams and large windows, filling the area with natural light. A dining table with six chairs is positioned centrally. A cozy seating area includes a sofa and armchair, while a staircase leads to the loft bedroom above.
Cottage in Rhinebeck
4.99 out of 5 average rating, 153 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

LizRating, 5 stars2 weeks ago
By far one of the best airbnbs I have ever stayed at! The cabin was beyond adorable, comfortable, clean, so well decorated and very private. It was so relaxing with great outdoor areas to hang out, places inside to read, comfortable den to watch movies and super comfortable bed. Would definitely come back!!
Guest favorite
Cottage in Lanesville
4.95 out of 5 average rating, 187 reviews

Creekfront Cottage between Phoenicia & Hunter Mtn.

BrittanyRating, 5 stars1 month ago
We loved our stay at the cabin and hope to be back soon! It’s was the perfect place for us to stay for our week upstate. We loved the movie collection and listening to the sounds of the creek from the open windows. Really feels like you are at someone’s home and not a soulless rental! Five stars ❤️
Top guest favorite
A cozy window nook features a cushioned seat adorned with pillows, offering a serene view of the surrounding trees. Natural light fills the space, highlighting the warm wooden accents and inviting atmosphere. A soft throw blanket is draped over the side.
Cottage in Haines Falls
4.99 out of 5 average rating, 147 reviews

The Kaaterskill Cottage - views of Hunter Mtn!

BenjaminRating, 5 stars2 months ago
We've stayed at Jenna's home a few times. Each of our visits have beeen wonderful. Her home is pristine, extremely comfortable, and very well thought-out for easy use by guests. The kitchen is very well equipped. Things like thoughtful labels on light switches, quality linens, very comfortable mattresses, nice towels, a complete lack of clutter while still being thoughtfully decorated, always makes us feel very comfortable in this space. The area is very peaceful and quiet. We will gladly continue to return!
Guest favorite
Cottage in High Falls
4.97 out of 5 average rating, 102 reviews

The Carriage House

EmileRating, 5 stars1 month ago
We had a wonderful stay at The Carriage House and would definitely book it again. It felt like a true escape from city life. Very cozy and comfortable and had everything we needed. The house was perfectly located near High Falls, Accord and Stone Ridge so we got to eat at great places and explore each of the towns without needing to spend much time in the car. Would recommend this place for anyone looking to spend some time in that area. It was truly a lovely experience.
Superhost
An open-concept living area showcases timber ceilings and large windows allowing natural light to fill the space. A wooden sofa is paired with a colorful area rug, while a dining table and kitchen are visible in the background. A staircase leads to the lofted sleeping area.
Cottage in Accord
4.86 out of 5 average rating, 111 reviews

Cottage w Pond Pet Friendly | Near Attractions

DJRating, 5 stars2 weeks ago
I absolutely loved this place. Extremely simple and clean, yet has everything you could need. Ana and Peter were communicative and kind hosts. I will stay here again any chance I get!

Cottage rentals with a pool

Guest favorite
A heated pool is surrounded by a stone patio and secured by a metal fence. Lounge chairs line one side of the pool, with a serene wooded backdrop providing privacy. Morning light reflects on the water's surface, creating a calm and inviting atmosphere.
Cottage in Clinton Corners
4.89 out of 5 average rating, 169 reviews

Tranquil Cottage in the Country

MaureenRating, 5 stars1 month ago
Craig’s place was great! Bedrooms were a good size and beds were very comfortable. Nice open living space. Beautiful grounds. Everything was clean and we had whatever we needed in the kitchen. Very private and quiet location. Would definitely stay again!
Superhost
A serene outdoor pool area is surrounded by a wooden deck and natural greenery. Pool floats lie on the water's surface, and a few lounge chairs are arranged nearby. Lush trees and shrubs create a tranquil backdrop, enhancing the connection to nature.
Cottage in Kingston
4.81 out of 5 average rating, 175 reviews

Cottage with Private Deck on 8 acres of Woods

CarolineRating, 5 stars5 days ago
The stay at Ashlie’s was just perfect. The cabin is so intimate and secluded, but very close to everything you might wanna check out! Ashlie was very friendly, I would definitely stay again!!
Guest favorite
A spacious pool area features a vibrant blue pool surrounded by a stone deck. A nearby cabana is visible, with seating areas beside it, all set against a backdrop of lush greenery and trees.
Cottage in Pine Bush
4.89 out of 5 average rating, 272 reviews

Seclusion and Romance - Pool is open and heated!

KarenRating, 5 stars2 days ago
Although there is a lot to do within a short distance (hiking, bars, etc..), I chose this place specifically for the fenced in pool area. Coming from a NYC apartment with a dog and no outdoor space, this was exactly what I was looking for and better than expected. My dog was able to roam freely the entire day while we relaxed and lounged out by the pool or sat on the patio furniture by the fireplace that was completely covered and shaded. Richard's place did not disappoint!
Guest favorite
A heated saltwater pool is set within a gated bluestone patio, surrounded by lush greenery. The clear blue water reflects sunlight, creating a serene atmosphere. The pool area is framed by a mature tree line, providing privacy and a peaceful outdoor space.
Cottage in Kingston
4.92 out of 5 average rating, 379 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

TaliRating, 5 stars4 days ago
The cottage is lovely, clean, and immaculately decorated. Great taste. We enjoyed the pool, which was perfect for our four year old given how shallow half of it was, and how the temperature was perfect, even on days when it wasn’t too hot outside. We hadn’t realize that the kitchen didn’t include an oven or microwave—but even so, we had a great time and enjoyed the fire pit! WiFi was a bit spotty but the hosts went above and beyond to try to help. Highly recommend!
Top guest favorite
A heated, saltwater pool is surrounded by stone patio, with trees providing a lush backdrop. The water's turquoise hue reflects the sunlight, creating a serene atmosphere, while the adjacent landscaped gardens enhance the peaceful setting.
Cottage in Woodstock
4.97 out of 5 average rating, 37 reviews

Cottage in Woodstock | Heated Pool • Fire Pit

CalebRating, 5 stars1 month ago
We had a great stay. The location is great, close enough to town for easy access, but not too close. The beds are very comfortable, even the foldout couch. It is a wonderful place to be if you do not want to be bothered. Laurie is great, easy and relaxed
Superhost
A wooden deck is furnished with comfortable seating and a coffee table, providing a serene view of rolling mountains and a tranquil pond. The sky is filled with fluffy clouds, reflecting warm hues as the sun sets, enhancing the natural beauty of the landscape.
Cottage in Denver
4.94 out of 5 average rating, 139 reviews

Country Cottage w/ HOT TUB & Views

ДианаRating, 5 stars3 weeks ago
Everything about our stay was perfect! The house was spotless, cozy, and located in a great area. The host went above and beyond — always in touch, helpful, and kind. We truly felt welcomed and taken care of. Would absolutely stay here again!
Guest favorite
The modern farmhouse is showcased beneath a clear sky, featuring a spacious deck that overlooks a well-maintained in-ground pool. Two lounge chairs are positioned beside the water, with colorful outdoor furniture and a striped umbrella providing comfort and shade.
Cottage in Accord
4.95 out of 5 average rating, 123 reviews

Light-Filled Upstate Home, Perfect Location

SelimaRating, 5 starstoday
We had a lovely stay at Marco’s house! It was one of the cleanest Airbnb’s I’ve stayed at! We stayed during a heatwave and were so happy to have the pool! A mom and baby deer and a few rabbits would come by while we were in the pool. Our daughter loved it! The AC also worked perfectly and kept the house cool during the heatwave. Marco was lovely to interact with - he was very responsive and accommodating. We loved their local recommendations and can’t wait to come back!
Guest favorite
An aerial view captures the serene landscape surrounding the cottage, featuring a bright blue pool bordered by a wooden deck. Lush greenery envelops the area, with trees providing shade and a sense of seclusion, while the cottage sits nestled in the background.
Cottage in Woodstock
4.81 out of 5 average rating, 116 reviews

Woodstock Mountain Cottage w/ Pool

DinaRating, 5 stars2 weeks ago
We had an amazing stay at the cottage! It's modern and thoughtfully designed, but still feels cozy and inviting. It’s tucked away in a peaceful spot surrounded by trees, yet only a 3-minute drive from town. You feel totally removed and relaxed, but everything you need is right nearby. I worked remotely for part of the trip, and the setup was perfect. There’s a dedicated desk with a view of the mountains, and the Wi-Fi was fast and reliable. Natural light poured into the cottage through the skylights. It was spotless and comfortable. The bed and linens were top notch, water pressure was great and hot—little details that make a difference. The pool was a highlight. It’s heated, with plenty of loungers and umbrellas, and it felt totally private and calm. We ended up spending an entire day out there just soaking it in. The hosts were lovely. They were helpful when we needed them, but also gave us complete privacy. We’d absolutely come back and highly recommend this place to anyone!

Cottage rentals with a hot tub

Guest favorite
A hot tub is surrounded by lush greenery and illuminated by string lights, creating a serene outdoor setting. A stone path leads to the hot tub, with red chairs visible nearby, all nestled within a wooded area.
Cottage in Mongaup Valley
4.97 out of 5 average rating, 236 reviews

Hot Tub, Playground, 3 Acres, and Much More!

GilbertRating, 5 stars3 weeks ago
Highly recommended — especially for families with young children! The property has everything you could need, and there’s even a charming farm nearby (just be sure to check their hours in advance). The hosts were incredibly responsive and helpful throughout our stay. The house was spotless and had such a welcoming, positive energy. With so much land to explore, you truly don’t need to leave the property if you bring your own food and supplies. We had a wonderful experience and will definitely book again in the future!
Guest favorite
A cozy living room is displayed, featuring a comfortable sofa, a wooden coffee table, and a wall-mounted television. Natural light enters through a window, accompanied by decorative plants. A dining area with high chairs is positioned nearby, contributing to the inviting atmosphere.
Cottage in Bloomington
4.96 out of 5 average rating, 234 reviews

Couples Getaway, Hot Tub, 3 acres, 5mi to Kingston

NoaRating, 5 stars1 month ago
We had a lovely stay at kim’s. The location was great, having a hot tub was really nice even with the weather getting warmer, the space was very clean and kim was very responsive to us throughout the whole stay.
Guest favorite
A bright living area features a cozy sectional sofa and a plush white couch, arranged around a circular area rug. A modern gas fireplace is set into the wall, with soft light emitted from nearby lamps and natural light streaming through the windows.
Cottage in Saugerties
4.89 out of 5 average rating, 186 reviews

Hits Adjacent | Pet Friendly | Caraway Cottage

LucyRating, 5 stars1 week ago
The perfect stay for horse showing at HITS! My only hesitation in writing this review is that I didn't want anyone else to know about this place for future horse shows! ;) An excellent place to stay with above and beyond amenities, easy check in and great for traveling with a dog. Will absolutely be back!
Guest favorite
The spacious deck is softly illuminated by string lights, creating a serene atmosphere. A jacuzzi, elegantly positioned, offers a relaxing retreat, while surrounding trees provide a sense of seclusion as night falls.
Cottage in Monticello
4.9 out of 5 average rating, 122 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

BrianaRating, 5 stars2 weeks ago
Beautiful, cozy, and comfortable cabin. Bilen was extremely clear & communicative with instructions and local recommendations. We especially enjoyed the record player and having access our own private hot tub on the deck, the surrounding woods are gorgeous and many deer friends paid us a visit! Would absolutely recommend, thank you for the lovely stay!
Superhost
A stone pathway leads to a charming cottage nestled among lush greenery. Vibrant yellow flowers and dense foliage frame the entrance, creating an inviting atmosphere. Towering trees provide shade, while a trellis adorned with flowering vines arches over the path, enhancing the cottage's serene setting.
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars1 month ago
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!
Guest favorite
The entrance of a cottage is framed by lush greenery, showcasing a welcoming wooden porch and a dark door. Potted plants add a touch of charm to the inviting pathway, which leads through a grassy yard.
Cottage in Boiceville
4.98 out of 5 average rating, 114 reviews

Hot Tub & Chic Catskills Woodstock Design Retreat

JordanRating, 5 stars4 months ago
We always stay at Little Willow when we go skiing at Belle Ayre. I think our three years and running relationship with the house tell you all you need to know about working with the Little and Littler gang and their spot.
Guest favorite
The inviting living area features a comfortable gray sofa adorned with accent pillows. A wooden coffee table is centrally placed, while a modern lamp and a cozy rug enhance the space. Large sliding doors open onto the deck, offering natural light and views of the surroundings.
Cottage in Chichester
4.93 out of 5 average rating, 108 reviews

Stream Come True | Hot Tub, Ski, Hike, Relax

AmyRating, 5 stars2 weeks ago
Really a beautiful, peaceful escape. Easy drive to so many adventures! Hot tub while listening to the creek... chef's kiss. Just be prepared for mosquitos, wow. But there was bug spray and citronella candles to help.
Guest favorite
The image captures a vibrant sunset over a tranquil lake, with an array of warm colors reflected in the water. Soft clouds scatter across the sky, framing the peaceful scene. The surrounding landscape features silhouettes of trees along the shore, enhancing the natural beauty.
Cottage in Bethel
4.96 out of 5 average rating, 116 reviews

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK

KelliRating, 5 stars1 week ago
Great place. Fun water activities for the kids. Our dogs allowed to come was excellent. A little light on cutlery in the kitchen, but we made it work. Would recommend and would stay here again!

Quick stats about cottage rentals in Woodstock

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 before taxes and fees

  • Total number of reviews

    4K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  4. Ulster County
  5. Woodstock
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