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Vacation rentals in Willow

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Top-rated vacation rentals in Willow

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A gently flowing stream meanders alongside the property, bordered by smooth stones and lush greenery. Vibrant autumn foliage enhances the serene landscape, with a glimpse of the cottage visible in the background, nestled among the trees.
Cottage in Willow
4.86 out of 5 average rating, 260 reviews

Peace Cottage

Sweet Streamside Cottage in the magical hamlet of Willow in the town of Woodstock NY. Every surface is wiped and cleaned meticulously. Feng Shui Designed. Ski and Snowboard- Minutes to Belleayre , Hunter and quick drive to Windham. Hike the mountain with beautiful foliage, enjoy the hammock & fetch with your pup. Peaceful setting to unwind, work remotely, go deep into meditation or celebrate with your crew. We are conveniently on the Trailways route to NYC & can arrange solo or group retreats

Guest favorite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 366 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Top guest favorite
Cabin in Willow
5 out of 5 average rating, 117 reviews

Mountain Home with firepit and breathtaking views

Find refuge and relaxation when you stay at "Hickory House;" a newly renovated mountain home on 4 secluded acres in Willow, NY. This 3-bedroom, 2-bathroom home is the ideal place to hang your hat whether you're on a ski-filled family holiday or looking for a few sleepy days off the grid with friends. The living area embodies what Hickory House is all about: vaulted ceilings, a gigantic wood burning stove, plush seating, and a record player to boot will have you feeling all those upstate vibes.

Guest favorite
A wooden deck features a woven chair and a small, decorative table with a mosaic top. A lantern is positioned in the center of the table. Lush green trees surround the rustic cabin in the background, providing a serene and natural setting.
Cabin in Willow
4.93 out of 5 average rating, 293 reviews

Woodstock Cabin in the Woods #2

We offer a rustic, cozy and clean studio cabin for you to enjoy and make your home base while you explore the area. It's an intimate space to relax & rejuvenate in. We are located between Woodstock and Phoenicia making it easy to explore the eclectic shops and delicious restaurants and awesome hiking. Great skiing can be found 30-45 minutes away depending on the mountain you choose. Please read details thoroughly, so you can ensure a great getaway! We look forward to hosting you and yours!

Top guest favorite
An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.
Cottage in Saugerties
4.95 out of 5 average rating, 339 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

Top guest favorite
A tri-level wooden house is surrounded by trees and foliage, showcasing earth tones of the exterior. A spacious deck with chairs invites relaxation, and large windows provide natural light to the interior. The serene woods emphasize the home's secluded setting.
Home in Willow
4.97 out of 5 average rating, 115 reviews

Relaxing House in Catskills, w/Pretty Pond Nearby

Comfortable, nicely furnished, tri-level house nestled in the woods on a dead-end road (barely a car goes by) with seasonal mountain views. Good kitchen. Each bedroom has its own full bath. Hiking trails, skiing, and fishing nearby; sweet pond/picnic spot with waterfall a short walk away. Accommodates 4 adults, 2 in each BR. Additional guests should be children, as per local laws. There’s a sleep sofa in the lower level and a sleep chair in the master BR. Town of Woodstock Permit #20N-079

Guest favorite
A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.
Home in Mount Tremper
4.93 out of 5 average rating, 247 reviews

Mt. Wonder: Cozy Cabin w/ Hot Tub and Wow View

Welcome to the Wonder of the Catskills. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Just 10 min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub & an overall magical feel. Amenities galore incl the tub, BBQ, firepit, wood stove & stocked kitchen. Peruse our books, vibe in nature or enjoy hikes & cute towns nearby.

Guest favorite
A small dining area is seen with a round wooden table and a patterned chair. A large window offers a view of the outdoors with trees and a rustic shed visible beyond. A piece of artwork is displayed on the wall, enhancing the cozy atmosphere.
Guest suite in West Shokan
4.94 out of 5 average rating, 192 reviews

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

Top guest favorite
Aerial view of a rustic cabin surrounded by trees, showcasing a spacious wooden deck with outdoor seating and a fire pit. Warm light glows from the interior windows, while smoke rises gently from the chimney, indicating a cozy atmosphere in the woods.
Cabin in Bearsville
4.98 out of 5 average rating, 102 reviews

Catskill Cabin in the Woods

Our little Cabin in the Woods is a cozy place to unwind, build a fire, and enjoy the nature that surrounds you. Wake up in the morning to deer and wild turkeys roaming in the forest outside, and enjoy your coffee in the sunroom, on the back deck or on a walk to nearby Cooper Lake. Downtown Woodstock is an 8 min drive, while other local favorites The Pines and Phoenicia Diner are within 15 minutes. Close by hiking trails abound as well, with the famous Overlook Mountain under 5 miles away.

Top guest favorite
An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.
Cabin in Saugerties
4.97 out of 5 average rating, 110 reviews

Luxury A-Frame Cabin in the Woods with Sauna

Modern, glass‑fronted A‑frame perched in the Catskills, offering sweeping mountain vistas. Relax in the private cedar barrel sauna & refreshing outdoor shower, gather round the smokeless propane fire-table, or fire up the propane grill for al‑fresco dinners. A stylish bedroom with woodland views, luxe linens, fast Wi‑Fi, and a cozy electric fireplace blend comfort with design. Minutes to trailheads, waterfalls & farmers markets - ideal for couples seeking a serene and restorative escape.

Top guest favorite
Guest suite in Woodstock
4.99 out of 5 average rating, 188 reviews

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Top guest favorite
A unique three-story silo home is showcased, featuring a wooden exterior and numerous windows glowing warmly. Surrounded by snowy landscapes and trees, the structure is complemented by a wooden deck leading to an inviting red door.
Chalet in Willow
4.9 out of 5 average rating, 168 reviews

Cozy Silo Home w Mountain Views near Woodstock

The charming Willow Silo is nestled amongst the trees 10 minutes away from Woodstock and 15 minutes away from Phoenicia, this wondrous three story tower is well positioned to hiking nearby woods and mountains, as well as waterfalls. Wake up to a spectacular view of the mountain from the main bedroom or deck and end the evening stargazing from our own hammock by night. Secluded in the woods for a perfect relaxation retreat! ! PERMIT No: 23N-277

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