Cottage vacation rentals in Woodstock

4.96 out of 5 average rating, 183 reviews

An open living area is highlighted by a wood-burning stove, providing warmth to the space. A dining table with chairs is positioned adjacent to large windows, allowing natural light to fill the room. A globe and a cozy blanket add decorative touches.

Cottage in West Shokan

Catskills Getaway w/AC 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, 131 reviews

A stand-alone guest house is framed by lush greenery, featuring a prominent wall of glass that allows abundant natural light. The exterior is finished in wooden planks, complemented by neatly landscaped flowerbeds at the base.

Cottage in Bearsville

Contemporary Guesthouse with Views and Privacy

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 red house with yellow trim features a welcoming front porch and multiple windows. The porch is accessed by a set of steps and surrounded by a well-maintained yard with trees and shrubs, providing a charming entryway.

4.85 out of 5 average rating, 270 reviews

Woodstock Dog Friendly Cozy Cottage in Town + 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, 325 reviews

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

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.

An open-plan living area is illuminated by natural light from expansive sliding glass doors. A small dining table with two chairs sits beside the doors, while a full kitchen and refrigerator are visible in the background. Light wood flooring contrasts with a woven area rug.

4.93 out of 5 average rating, 127 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).

5 out of 5 average rating, 410 reviews

The cozy cottage is surrounded by a lush green lawn, with a wooden deck and twinkling string lights creating a charming ambiance. A vibrant flower bed with sunflowers adds a splash of color, while the nearby creek offers serene water views.

Cottage in Saugerties

Carriage House on Falls, Walk to Village

Welcome to 1903 Carriage House on the Falls — just down the hill from the vibrant village of Saugerties. This cottage blends modern comfort with rustic charm. Its cozy size makes it the ultimate escape for couples seeking a tranquil getaway. Admire panoramic creek vistas from the back deck. Enjoy the outdoors with a gas grill and waterside gazebo, unwind with board games, or relax with a movie on the SmartTV. As night falls, drift off to the soothing sound of the waterfall.

A charming cottage exterior is framed by lush greenery. The entrance is marked by a fenced patio area with a gravel path leading to the door. Potted plants add a touch of greenery, while a shaded seating area with a fire pit invites relaxation.

4.99 out of 5 average rating, 172 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 charming cottage sits nestled in green surroundings, featuring a front porch with two inviting chairs. A spacious lawn leads up to the entrance, framed by trees that provide natural shade. Light filters gently through the foliage, accentuating the peaceful setting.

4.91 out of 5 average rating, 493 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.

4.96 out of 5 average rating, 215 reviews

A cozy cottage is set within a wooded landscape, featuring a combination of black exterior and a warm wooden porch. Four Adirondack chairs surround a fire pit, with colorful plant arrangements enhancing the natural setting among fallen leaves.

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, 166 reviews

The exterior of the house showcases a charming two-story structure with light siding and a vibrant red front door. Lush greenery surrounds the property, complemented by a well-maintained lawn and a pathway leading to the entrance.

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.

A cottage is presented with a warm wooden facade, surrounded by lush greenery. A small porch is accessible from the front entrance, and landscaping features tidy garden beds with a variety of plants. Dense trees provide a natural backdrop, enhancing the tranquil setting.

4.95 out of 5 average rating, 305 reviews

Woodstock Streamside Cottage

Our streamside cottage is located on a five acre property under a mile to the center of Woodstock. The Sawkill Stream is your backyard with plenty of beautiful trees and meadows your front yard. Quiet sounds of the stream and nature surround you. Central heat and central a/c keeps you comfortable year round. Newly renovated. Please read our reviews and see how you'll feel. Enjoy!

A modern kitchen features cabinetry in natural wood tones, complemented by a tile backsplash. Stainless steel appliances are visible, including a refrigerator, stove, and microwave. A dining table for two is set with wine glasses and simple place settings, while large windows provide ample natural light.