When one hears of Woodstock, the image of hippies, festivals, and Jimi Hendrix captivating an audience with his rendition of the “Star-Spangled Banner” might come to mind. While Woodstock is known for its celebrations, there is plenty more to see and do in the area. Tourists can immerse themselves in nature by hiking Indian Head Mountain, swimming in the Ashokan Reservoir, or wandering through the sculpture garden at Opus 40. There are also plenty of boutique art stores and restaurants to discover.
Whatever your reasons for visiting this beautiful area of New York, you’ll want to be guaranteed of arriving at top-notch accommodation. We at Road Affair want that for you, too, which is why we have crafted a list of the best Airbnbs in Woodstock. All of the listings below are hosted by Airbnb superhosts, and some even boast Airbnb Plus status. For those unfamiliar with Airbnb, superhosts are rental owners with a history of providing outstanding hospitality to their guests, and Airbnb Plus is an elite program that highlights exemplary homes that have been in-person verified for quality assurance.
Related: 15 Best Airbnbs in New York, USA
Cozy Stone Cottage in West Hurley
Kicking off our list of the best Airbnb rentals in Woodstock is this gorgeous studio-style stone guesthouse.
This Airbnb Plus is located on superhost Linda’s property but provides plenty of privacy. Inside, the home features a rustic motif with comfortable furnishings, high ceilings, and exposed wood beams. In the living area, guests can unwind on the couch in front of the stone fireplace and stream their favorite shows on the Smart TV. There is also a selection of magazines to choose from. The full kitchen has all the essentials for cooking, and guests can enjoy their meals at the two-person breakfast table or the dining table.
In the living area, there is a double-size Murphy bed that folds down where guests can get a good night’s rest or snuggle up and watch a movie. Beside the bed, there is a selection of board games and a luggage rack. The bathroom is stocked with complimentary shampoo and soap, as well as a hair dryer.
Outside, guests can lounge in the hammock in the garden and read a book or enjoy a nap in the afternoon sun. There is also a barbeque and a firepit.
Historic Barn With a Yoga Studio
This reimagined 19th-century barn has been completely converted into a gorgeous three-bedroom farmhouse, perfect for families or groups of up to eight.
Inside, the home features a country-modern motif with colorful décor, wood floors, and exposed brick. In the living room, guests can snuggle up in front of the brick fireplace and listen to music on the Amazon Echo or set up the projector and access their favorite streaming services. The full kitchen boasts stainless-steel appliances and has plenty of counter space for preparing meals. In the dining area, there is a lovely six-person table, as well as a library of books and board games.
All three bedrooms are equipped with queen-size beds and have plenty of storage space for clothes. The third bedroom also has a desk for those planning on working remotely while on holiday. Guests can opt for a relaxing rinse or a bubble bath in the bathroom’s tub/shower combo. There is also a separate laundry closet with a washer and dryer.
In the evening, guests can relax on the porch’s day bed while enjoying a glass of wine. There is also a barbeque outside available to use and a yoga area upstairs.
The Pond House
If you are looking for a family-friendly Airbnb that can accommodate up to five guests, then this house rental in Woodstock is for you.
The interior of this Airbnb Plus boasts a stylish modern feel with textured walls, stunning art pieces, and high ceilings. In the master bedroom, guests can snuggle up on the king-size bed and enjoy fantastic pond views from the wall-to-wall windows. The second bedroom features a queen-size bed and a desk, while the third bedroom has a single bed and children’s books and toys. All of the bedrooms are equipped with heated floors. After a day of adventuring, guests can choose between a relaxing rinse in the bathroom’s walk-in rain shower or a soothing soak in the bathtub.
The full kitchen comes stocked with stainless-steel appliances and all the essentials for preparing meals. There are plenty of seating options in the living room where guests can unwind with a book from the library or gather for a movie night with the Smart TV. In the evening, guests can head outside and enjoy a few cocktails at the patio dining set or around the firepit while overlooking the pond.
The Mountain View Guesthouse
If you are looking for a pet-friendly house for rent in Woodstock with incredible mountain views, then consider staying at superhost Harvey’s guesthouse retreat in Shady.
Outside, guests can watch the sunrise over Mt. Guardian while enjoying a cup of coffee on the hammock chairs on the patio. There is also a barbecue and a hammock in the backyard, plus plenty of space for pups to run.
Inside, the home features a modern motif with sleek furnishings, wood accents, and plenty of natural light. In the living room, guests can light a fire in the woodstove and read a book from the library, watch a movie on the TV, or break out one of the board games for a family game night. The full kitchen comes equipped with all the cooking basics plus an antique-style manual coffee grinder from MoMA.
In the bedroom, there is a comfortable queen-size bed and room-darkening shades. The bathroom comes fitted with a gorgeous stone sink and a walk-in shower. Harvey also supplies guests with a hair dryer, shampoo, and soap.
Modern Cottage With a Hot Tub
Enjoy a glass of wine while stargazing from the private hot tub in this luxurious rental house in Woodstock.
This dog-friendly Airbnb is perfect for couples or families. Guests have access to a large backyard, as well as a patio that is decked out with a private hot tub, a hammock, and a screened-in porch.
Inside, the home features a minimalist-modern motif with stylish furnishings and vaulted ceilings. In the living room, guests can peruse the vinyl collection and play some tunes on the record player or settle into the couch for a movie night in front of the fireplace. The full kitchen boasts sleek black cabinets, stainless-steel appliances, and a quaint breakfast bar. Guests can enjoy their meals at the gorgeous six-person wood dining table. In the basement, there is a second family room with a large sectional sofa, a TV, and a bar.
After a day of hiking, guests can tuck into the plush king-size bed in the master bedroom. The second bedroom has a queen-size bed, and the third bedroom is perfect for kids as it is equipped with two single beds and board games. There are two full bathrooms, one with a walk-in rain shower and the other with a standard walk-in shower. Both bathrooms come with a walk-in shower.
Cozy Cottage for Two
This cabin rental in Woodstock is perfect for solo travelers or couples looking for a private forest getaway.
The home is surrounded by a lovely wooded area, offering plenty of privacy and fall foliage. Guests can enjoy their morning coffee on the patio dining set and watch the birds flutter around in the morning air.
Inside, the cabin features a contemporary motif with colorful décor, modern furnishings, and a touch of country charm. After a day of hiking, guests can return for a relaxing bubble bath in the bathroom’s soaking tub, then cuddle up in the bedroom’s queen-size bed for a good night’s sleep.
The full kitchen is equipped with all the essentials, including a kettle, coffee maker, and a gas oven. Guests can enjoy their meals at the dining table surrounded by wall-to-wall windows. In the living room, there is a lovely stone fireplace and a Smart TV that is perfect for binge-watching shows and movies.
This Airbnb in Woodstock is only a five-minute drive from downtown Woodstock. Overlook Mountain Trailhead is 10 minutes away by car, and Cooper Lake is roughly a five-minute drive away.
Contemporary Cottage Near Woodstock Golf Club
This gorgeous two-bedroom Woodstock Airbnb is perfect for couples or families looking to stay close to the restaurants and shops of the town.
The home is located less than a one-minute drive from the Woodstock Golf Club and is within walking distance to coffee shops, grocery stores, and restaurants. Belleayre Mountain Ski Center is roughly a 35-minute drive away, and Overlook Mountain Trailhead is less than a 10-minute drive away.
Inside, the home boasts a charming contemporary feel with whitewashed exposed beams, colorful artwork, and large picture windows. In the living room, guests can relax on the couch in front of the fireplace and read a book or watch a movie on the TV. The full kitchen comes equipped with stainless-steel appliances, a breakfast bar, and cooking spices.
The master bedroom is quite spacious and includes a king-size bed, a built-in closet, a couch, and a TV. In the second bedroom, there is a queen-size bed, a desk, and an en suite bathroom with a walk-in shower.
Outside, guests have access to a private fenced-in yard with a patio dining set and a barbecue.
Romantic Getaway for Two
Are you looking to whisk your partner away on a romantic countryside weekend getaway? Well, then, consider renting this stunning Airbnb Plus in Saugerties.
The guesthouse boasts an open floor plan with wood-paneled ceilings, ambient lighting, and wood accents. In the bedroom, guests can snuggle up in the plush queen-size bed for a good night’s rest. The living room features a stylish velvet box chair and a couch, perfect for cozying up for a movie night. There is a lovely blue backsplash in the full kitchen, along with complimentary tea and coffee.
A rustic barn door slides back to reveal the bathroom, where there is a walk-in shower. Guests need to climb the ladder in the living room to get to the loft-style bedroom, where there is a bed, offering a relaxing space to read.
If you and your partner are celebrating something special, make sure to let superhost Jeddah know, as she has been known to go above and beyond to make the space special for her guests. It should also be noted that Jeddah has stated that this Woodstock Airbnb Plus is not suitable for children or guests under the age of 25.
Peaceful Log Cabin
If you are looking to rent a cabin in Woodstock, then check out superhost Rachel’s gorgeous studio-style log cabin.
The interior of the home boasts wood-paneled walls, vaulted ceilings, and colorful plants, creating a country-contemporary feel. In the living area, guests can curl up on the couch and watch a movie or plan their next day’s adventure. There is also a dedicated workspace with a desk and chair, perfect for those planning on working remotely while on holiday.
In the bedroom area, there is a comfortable queen-size bed. The full kitchen comes equipped with all the essentials, including a coffee maker and a toaster oven. Rachel also supplies fresh baked goods.
Guests can ask Rachel to meet the horses or roam the farm and check out the ducks around the pond. There is also a small picnic area, perfect for enjoying an afternoon lunch in the sun.
This Airbnb in Woodstock is located just outside of Saugerties, about a 10-minute drive from Woodstock and a 15-minute drive from the Saugerties Lighthouse. There are plenty of hiking trails nearby.
Stylish Studio Apartment in Woodstock
This lovely short-term rental in Woodstock is ideal for couples or solo travelers looking to be within walking distance of the town center.
The home is located right across from the Woodstock Flea Market, which is open all summer long. There are plenty of coffee shops and restaurants steps from the apartment, and guests have access to free on-site parking.
Inside, the home features a contemporary feel with whitewashed walls, wood furnishings, and plenty of natural light. In the bedroom/living room area, there is a stylish light blue couch and a queen-size bed where guests can relax and watch TV or read a book. The kitchenette comes well equipped with a minifridge, a two-burner stovetop, a microwave, a toaster oven, and a coffee maker. Guests can enjoy their breakfast at the three-person dining table. There is a walk-in shower in the bathroom, along with a makeup mirror that is ideal for getting ready for a day about town. Superhosts Wendy and James also provide complimentary toiletries like shampoo and soap.
Two-Bedroom Cottage Near Ashokan Reservoir
This beautiful log cabin is the ideal vacation rental in Woodstock for couples or solo travelers looking to embrace nature.
Guests have access to a large backyard surrounded by forest. There is a partial wrap-around deck with a barbecue, lounge chairs, and a patio dining set, perfect for afternoon cookouts. In the evening, guests can gather around the firepit with a couple of beers and roast marshmallows.
Inside, the cabin boasts a vaulted ceiling with skylights and country-style décor, creating an inviting and stylish space. In the living room, guests can curl up beside the woodstove and watch a movie on the Roku TV or gaze out the picture windows in search of deer. The full kitchen is well stocked and comes with a dishwasher, chef’s knives, and much more. Guests can enjoy their meals at the two-person breakfast table.
In the master bedroom, there is a cozy double bed with French door–style windows in front of it that can open to let the fresh air in. The second bedroom has a reading chair and a single bed.
Retro Guesthouse
Step back in time at this 1970s-inspired, pet-friendly vacation home for rent in Woodstock.
Once featured in Playboy, this retro apartment is perfect for couples or solo travelers looking for a unique Airbnb in Woodstock. The home boasts wood-paneled walls with vintage furnishings and modern touches. In the bedroom area, there is a comfortable double bed, a vintage radio, a vinyl player, and a comfortable reading chair. There is also a Roku TV and a small desk with a chair, perfect for those planning on working remotely while on holiday. A crib is also available for guests traveling with little ones.
The kitchenette has all the basics, including complimentary tea and coffee, a toaster oven, and a minifridge. Guests can enjoy their meals at the breakfast bar. Superhosts Martin and Erin have stocked the bathroom with amenities like shampoo, conditioner, body wash, and a blow dryer.
Guests also have access to bikes that they can use during their stay. There is a bar and ice cream shop two blocks away and a yoga studio one block away.
Spacious House With a Hot Tub
This one-bedroom house is one of the best Woodstock Airbnbs for couples or solo travelers looking to spend some leisure time outside.
In the backyard, guests will find a lovely private area with a firepit, Adirondack chairs, a barbecue, and a hot tub, all underneath sparkling fairy lights.
Inside, the house features a beautiful contemporary motif with nature-themed décor, colorful furnishings, and plenty of homey touches. In the living room, guests can unwind on one of the couches and access their favorite streaming services on the Smart TV. There is also a lovely workspace area in front of a window with a desk and chair for those working remotely while on holiday. The full kitchen boasts gorgeous wooden countertops and is well equipped with stainless-steel appliances, chef’s knives, cutting boards, and much more. Guests can enjoy their meals family-style at the breakfast bar or the six-person dining table.
Upstairs, there is a massive bedroom with a queen-size bed, a desk, and a lovely sitting area with a couch and coffee table. After a day of adventuring, guests can return for a relaxing rinse in the bathroom’s walk-in shower.
Adorable Cottage in the Heart of Woodstock
This charming yellow cottage is the perfect Woodstock Airbnb for families or couples looking to stay close to the town center.
The home is located away from the road to provide privacy but is only a short walk to the restaurants and shops in the center of the village. There is a bakery and a restaurant and bar across the street. In the backyard, there is a lovely little forested garden area with a bistro set and a field with mountain views that guests can wander through on morning walks.
Inside, the cottage has a studio-style layout with a contemporary-country feel. In the living room/bedroom, there is an adorable king-size wicker bed and a reading chair where guests can curl up with a book. The kitchenette comes equipped with a coffee maker, a hot plate, and a toaster oven, along with other essentials. There is also a quaint two-person breakfast table where guests can enjoy their meals or work on their laptops. The bathroom is stocked with complimentary soap and shampoo, as well as a hair dryer.
Brookside Barn
If you are looking to rent a house in Woodstock that can sleep the whole family and has classic country charm, then look no further than superhost Amy’s spacious converted barn.
The house features a charming contemporary-country motif with stylish furnishings, exposed wood beams, and wood floors. The living room has plenty of seating places for guests to gather for a movie a night or unwind with a beverage. There is also a gorgeous stone fireplace and a vintage piano. The full kitchen is fitted with stainless-steel appliances and has plenty of counter space for cooking.
In the first bedroom and second bedroom, there is a queen-size bed and a single bed. The third bedroom has a queen-size bed. Guests can easily bathe little ones before bed in one of the two bathroom soaking tubs or rinse off in the shower. This Airbnb in Woodstock is ideal for groups who need to work remotely, as there are three separate dedicated workspaces throughout the house.
Outside, guests can enjoy a picnic beside the creek or gather around the firepit for a good old-fashioned s’more roast. There is also a barbecue available for use.
Well, there you have them, the best Airbnbs in Woodstock, NY! We hope that one of these fantastic Woodstock Airbnbs has caught your eye so that you can start packing for your vacation!
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