Cottage holiday rentals in Woodstock

A sparkling heated pool is framed by natural surroundings, with a stand-alone guest house visible in the background. Lush trees create a serene atmosphere, enhancing the privacy of the outdoor space. Nearby, seating areas and open grass provide inviting spots for relaxation.

4.97 out of 5 average rating, 147 reviews

Contemporary Guesthouse with 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.

ValueFamilyHiking

A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.

4.97 out of 5 average rating, 172 reviews

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

LocationFamilyLaundry

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, 302 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!

FamilyLocationBarbecue

A charming wooden cottage is set amidst lush greenery, featuring a welcoming entrance framed by low shrubs. The cottage's sloped roof and large front door invite guests into a serene environment, surrounded by trees and open space.

4.83 out of 5 average rating, 133 reviews

Woodstock Mountain Cottage w/ Swimming Pool

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, and hiking trails. We use strict cleaning protocols to ensure each stay is perfect and feels like home. The house is equipped with fast wifi and a ROKU Ultra for your tv needs! Located just 3 mins to the center of Woodstock. Swim in the pool, hike a trail, enjoy nature, grill or relax in the hammock. Pool is shared only with hosts & very private. No guests of guests allowed & no parties.

LocationFamilyComfort

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.

4.94 out of 5 average rating, 384 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.

LocationValueGetting around

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, 164 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).

FamilyLocationHospitality

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, 331 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. About 1.5 miles from the Ramble concert venue and 2.5 miles from the Bearsville Theater area. Enjoy!

FamilyLocationView

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, 203 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.

ValueFamilyIndoor spaces

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, 540 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.

ValueLocationOutdoor spaces

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.

4.96 out of 5 average rating, 265 reviews

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!

FamilyValueCheck-in

A cozy living area features a black sofa adorned with patterned throw pillows and a warm blanket. A wooden coffee table sits in front, complementing the space. In the background, a kitchen with bar stools is visible, along with a window allowing natural light.

4.94 out of 5 average rating, 316 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Located on a bucolic country road on the border between Saugerties and Woodstock, this newly renovated 500 sq ft cottage is on a private acre filled with spaces to relax: screened in dining shed, fire pit, BBQ grill, a creek, forest & the magical sound of a hidden waterfall across the road. Just 10 min from Woodstock town square, 8 min to Levon Helm Studios, and 15 from Bearsville Theater, it's the perfect escape. (Pets welcome on a case by case basis. Please ask.)

ValueFamilyRiver

4.97 out of 5 average rating, 101 reviews

A cozy bedroom features a spacious bed with neutral linens, complemented by a geometric accent wall. Nearby, a serene creek is visible with individuals enjoying the water, surrounded by lush greenery. An outdoor dining area showcases a wooden table set with a charcuterie board, while a well-lit living space offers a comfortable seating arrangement.

Cottage in Boiceville

Perch Cottages #3: Creek access + Sauna + Mt views

A group of modern cottages with spectacular mountain views, and magical creek frontage on the Esopus Creek (with its own beach and swimming hole!) Completely renovated. Quick 2 HR drive from the City. ✔ Fishing and Swimming ✔ 1 Dog or Cat per cabin allowed ✔ Gas BBQ Grill ✔ 40” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Onsite parking 7 mins → Ashokan Rail Trail 25 mins → Belleayre Ski Resort

ValueLocationRiver

Popular amenities for Woodstock cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.97 out of 5 average rating, 138 reviews

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

Catskills Woodstock Design Retreat w/ hot tub

FamilyLocationSkiing

4.94 out of 5 average rating, 152 reviews

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

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

LocationFamilyBarbecue

5.0 out of 5 average rating, 249 reviews

The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.

Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

FamilyLocationSleep quality

4.9 out of 5 average rating, 963 reviews

A spacious studio features a renovated ceiling with wooden beams and skylights. Large glass doors provide access to the outdoor area. Colorful textiles embellish the seating area, while a dining table is set with place settings. A kitchenette is visible in the background.

Cottage in Phoenicia

Romantic hot tub cottage. Hiking/breweries nearby.

LocationFamilyGetting around

4.92 out of 5 average rating, 174 reviews

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

Country Cottage w/ HOT TUB & Views

ValueFamilyDecor

4.98 out of 5 average rating, 155 reviews

The exterior of the cottage is set against a backdrop of lush greenery, with a spacious two-story design featuring a welcoming front porch. The surrounding landscape features a slope of vibrant grass leading towards the cottage, enhancing the serene rural setting.

Cottage in Monticello

Dutchhillcottage, gem in the southern Catskills.

ValueFamilyIndoor spaces

Cottage in Town of Gilboa

A living area features a cozy gas fireplace framed by a white mantel. Comfortable seating is provided with a gray armchair, vibrant red chairs, and a green ottoman in the center. A dining table for two stands to one side, with artful wall decor enhancing the ambiance.

4.92 out of 5 average rating, 397 reviews

Home Alone Mountain

ValueLocationBarbecue

A spacious living room is bathed in natural light from the floor-to-ceiling windows, revealing lush greenery outside. Cozy seating is arranged with colorful cushions, and a low coffee table holds a tasteful arrangement. Nearby shelves display various decor items, adding a sense of character to the space.

4.87 out of 5 average rating, 31 reviews

The Powdermill House | Catskills–Hudson Valley

ValueLocationAccess

Pet-friendly cottage rentals

4.99 out of 5 average rating, 191 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

FamilyValueAmenities

4.94 out of 5 average rating, 143 reviews

Cottage in West Camp

Hudson Valley Cottage

FamilyValueHeating

4.89 out of 5 average rating, 271 reviews

Cottage in Kerhonkson

Beautiful stream side cottage in the woods

FamilyValueCondition

4.95 out of 5 average rating, 350 reviews

A cozy living area showcases a brown sofa adorned with decorative pillows, complemented by a patterned area rug. A rocking chair sits nearby, and a wooden table holds a stack of books. Natural light enters through two windows featuring bamboo shades.

Cottage in Phoenicia

Cozy Catskill Cottage on the Pantherkill

ValueLocationDecor

A rustic wooden structure sits amidst a forested area, showcasing multiple windows and a cupola on top. A spacious porch extends from the front, framed by trees and natural greenery, creating a peaceful retreat atmosphere.

4.94 out of 5 average rating, 116 reviews

Mystical Moon Retreat near Woodstock, NY

FamilyLocationBackyard

4.93 out of 5 average rating, 126 reviews

A rustic cottage is surrounded by greenery, featuring a spacious wooden patio equipped with two blue Adirondack chairs. Large windows offer views of the outdoor area, and a sloped roof complements the design. Nearby trees provide shade and a natural setting.

Cottage in Chichester

Peaceful Cottage With Mountain Views

ValueLocationWalkability

4.99 out of 5 average rating, 654 reviews

A stone patio is surrounded by vibrant flowers and greenery, featuring a wooden table with four chairs. The cottage's large window provides a view of the inviting outdoor space, where additional potted plants add a touch of color and natural beauty.

Cottage in Chichester

Garden Cottage In The Catskills

ValueLocationBathroom

4.98 out of 5 average rating, 139 reviews

A comfortable living area presents a sectional sofa, accent chairs, and a wooden coffee table. Large windows allow natural light to fill the space, while a decorative area rug adds warmth. A small stove is positioned for added coziness, and colorful artwork adorns the walls.

Cottage in High Falls

The Carriage House

FamilyLocationCleanliness

Private cottage rentals

4.93 out of 5 average rating, 288 reviews

A spacious living area features a light-colored couch adorned with blue, green, and yellow pillows. A round coffee table sits in front of it, complemented by a rocking chair in green. A bright yellow wall and large windows enhance the room's openness.

Cottage in High Falls

Leggett Cottage

ValueFamilyAccess

A light-filled corner of the cottage features a wooden dining table with orange metal legs and two chairs. A vase of fresh flowers sits on the table, and sunlight streams in through nearby windows, illuminating the simple decor.

4.94 out of 5 average rating, 298 reviews

Blue Mountain Cottage

LocationValueIndoor spaces

A modern living area features a dark sectional sofa and a cozy coffee table, surrounded by an array of artwork on the walls. A large window allows natural light to illuminate the space, while a patterned rug adds warmth to the concrete floor.

4.99 out of 5 average rating, 198 reviews

Coldbrook Cottage

LocationValueView

4.8 out of 5 average rating, 174 reviews

WOODSTOCK COOPER LAKE COTTAGE

ValueFamilyCleanliness

A cozy living room features two light-colored sofas adorned with soft throw pillows and a warm blanket. A wooden coffee table holds a potted plant and magazines. A large window offers a view of the outdoors, while bright artwork adds a personal touch to the space.

4.97 out of 5 average rating, 186 reviews

Cottage on the creek with wonderful waterfall view

ValueLocationPets

4.98 out of 5 average rating, 118 reviews

Cottage in East Durham

Pawfect Family Retreat w/fenced-in yard & Dog Park

LocationValueComfort

4.94 out of 5 average rating, 316 reviews

A rustic cottage is surrounded by lush greenery, featuring a wrap-around deck illuminated by string lights. The wooden structure is complemented by various plants and shrubs, offering a serene and inviting atmosphere. The entry is adorned with a partially covered porch, enhancing the cottage's natural charm.

Cottage in Phoenicia

Charming creekside cottage in Phoenicia

LocationValueHiking