Cottage vacation rentals in Woodstock

4.96 out of 5 average rating, 173 reviews

The image displays a bright, airy bedroom entrance featuring light wooden flooring. A white armchair with a soft throw is positioned beside a small round side table. A doorway leads to the second bedroom, which is visible in the background through a partially open door.

Cottage in West Shokan

Cozy Catskills Getaway on 3 Acres near Woodstock

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

4.96 out of 5 average rating, 121 reviews

A serene waterfall cascades over a rocky ledge, surrounded by snow-covered trees. Icicles hang from the edge, and a gentle pool forms at the base, reflecting the tranquil winter scene. Soft white snow blankets the ground, creating a peaceful atmosphere.

Cottage in Bearsville

Contemporary Guesthouse with Private Heated Pool

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

A charming town square is highlighted with lush trees and neatly arranged stone pathways. In the background, a tall church steeple is visible against a cloudy sky, while the American flag gently waves. Benches are placed invitingly throughout the area.

4.84 out of 5 average rating, 257 reviews

Woodstock Dog friendly Cottage in Town; large yard

Charming Country Escape – Pet-Friendly & Walk to Village Green! Enjoy country charm and modern comforts in this newly updated 2-bed, 1.5-bath home. Just 2.5 blocks from the Village Green, it’s the perfect getaway for city folk with dogs. Relax in the private backyard with waterfall sounds or stroll to shops, restaurants, and trails. Features include a cozy woodstove, updated kitchen & bath, queen beds, and a master bedroom with an en-suite plus a balcony. You and your pet will love it here!

4.94 out of 5 average rating, 302 reviews

Cottage in Saugerties

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.

4.92 out of 5 average rating, 114 reviews

Mountain views, mid-century style! 1 mile to town.

Spacious, stylish, light filled studio guesthouse with gorgeous mountain views on 4 acre estate. Wake up to a view of the Catskills, seen through an expanse of sliding glass doors. Eat breakfast on the balcony, or relax on the couch while watching the sun go down. Inside: luxuriously comfortable, eco-friendly queen mattress, 50" smartTV, full kitchen, full bath. Outside: picnic table, hammock, cascading brook, land to explore. Good wifi inside/outside. (Woodstock STR permit #23H-279).

A gently flowing brook meanders over smooth stones, bordered by lush greenery. Sunlight filters through the trees, casting dappled shadows on the water. The tranquil scene invites relaxation, with natural elements harmoniously blending with the serene environment.

4.99 out of 5 average rating, 163 reviews

Luxury+firepit+stream+walk/town=Brook Cottage Too

Brook Cottage Too occupies the west wing of a newly-renovated 1928 Woodstock artist’s cottage featuring: oversize north-light windows; skylights; 1 bedroom w/king bed; spa-like bathroom; newly-remodeled kitchen; fire stove; bluestone patio w/gas grill + firepit; AC. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream + conservation land. Immaculately clean + available for long-term rentals, as well as short-term stays.

A vibrant display of blossoming flowers hangs from branches, showcasing shades of pink and white. The background features a lush green lawn that gently slopes towards distant, wooded hills under a partly cloudy sky with soft, diffused light.

4.81 out of 5 average rating, 116 reviews

Woodstock Mountain Cottage w/ Pool

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, & hiking trails. We use strict cleaning protocols to ensure every stay is perfect The house is equipped with fast wifi & a ROKU Ultra for all of your tv needs! The house is just 3 minutes driving to the center of Woodstock. In summer, swim in our pool, hike a nearby trail, grill or relax in the hammock. Our pool is shared with us strictly no guests of guests allowed.

A classic cottage is framed by tall trees, with a welcoming entryway and a small patio. Light green grass surrounds the home, and a stone walkway leads up to the entrance. Two chairs sit invitingly on the porch, offering a peaceful outdoor space.

4.91 out of 5 average rating, 473 reviews

Hidden Pines - Downtown Woodstock by Millstream!

Two blocks from Downtown Woodstock tucked away on a quiet lane sits Hidden Pines, a classic Woodstock Cottage. No need for a car here! Spacious light filled rooms and a bluestone terrace provide a soothing respite. Stroll down for a swim at the Millstream which is 1/2 block away. This cottage has been lovingly renovated and includes Central AC and heat. Please note this is a guest house. The main house is quietly owner occupied with its own private separate side yard.

4.97 out of 5 average rating, 202 reviews

A serene scene of the Saw Kill River is presented, framed by lush greenery. Smooth stones line the riverbed, while the gentle flow of water is visible through the gaps between the rocks. Sunlight filters through the trees, creating dappled patterns on the ground.

Cottage in Bearsville

Mirror Moon Cottage (waterfront)

Mirror Moon cottage is a newly renovated, original 1960's cottage in the heart of a historic arts and music community. The property is waterfront, overlooking the Saw Kill, with tranquil views & sounds. Imagine falling asleep to the sounds of the river on our hammock. Only an 8 min bike ride, or 4 min drive to the center of Woodstock town. It's subtly tucked into the woods, just outside of town. Perfect for a friends or couples getaway! Make yourself at home!

4.99 out of 5 average rating, 159 reviews

A view from the front porch showcases a lush green yard framed by trees and shrubs. A pot with a palm plant rests on the floor. In the distance, a glimpse of the Hudson River is visible, complemented by inviting lounge chairs on the lawn.

Cottage in Port Ewen

Swan Cottage with Expansive Hudson River Views

The Swan Cottage was built in 1923 and was fully renovated in 2020. The idyllic location, on a bluff overlooking the Hudson River, is the perfect perch to relax and get away from it all. The front porch is a nice spot to have a cup of coffee and watch the sailboats on the river, while the huge wraparound porch affords terrific views of the river as well as the forest that gives this home a feeling of being high in the tree tops.

4.99 out of 5 average rating, 174 reviews

A covered porch is showcased with a sectional sofa and accent cushions arranged around a low coffee table. A red chair provides additional seating. The surrounding forest offers a verdant backdrop, with sunlight filtering through the trees.

Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Stay at our comfortable and private 2-bed/2-bath home with covered porch, hot tub, fire pit, outdoor shower, and additional office cabin (perfect for work, exercise, or meditation) all surrounded by beautifully wooded forest. Centrally located in Kerhonkson just 15 minutes from local farm markets, popular farm-to-table restaurants and breweries, and hiking and other outdoor activities.

A peaceful streamside scene is captured, featuring a gently flowing stream bordered by smooth stones and lush greenery. Nearby, a simple wooden chair offers a spot to enjoy the soothing sounds of nature, surrounded by trees and vibrant foliage.