Family-friendly holiday rentals in Woodstock

The living and dining area features a combination of natural light and stylish furnishings. A warm wood dining table is surrounded by green chairs, while a cozy seating arrangement includes a leather couch and a unique wood slab coffee table. The space is enhanced by greenery from houseplants.

4.96 out of 5 average rating, 135 reviews

Maple House: Private/Romantic Walk-to-Town Oasis

Treat yourself to a romantic getaway or relaxing retreat in your own newly-renovated historic farmhouse, ideally located on a quiet dead-end lane just 1 block from the Woodstock Village Green ~ the heart of this famous “colony of the arts”. You can walk to restaurants, cafes, galleries, boutiques, theaters, clubs... Or you can stay home and relax in your private oasis of peace and beauty with a fully-fenced landscaped backyard, fireplace, chef’s kitchen, heated soaking tub, and luxury amenities.

5.0 out of 5 average rating, 458 reviews

A spacious master suite features a wooden accent wall and vaulted ceiling. A large bed with decorative pillows is positioned centrally, flanked by nightstands. In the background, a private bathroom is visible with modern fixtures and a wooden sink. Natural light filters through nearby windows.

Guesthouse in Woodstock

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1 1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

4.99 out of 5 average rating, 158 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

A light-filled living area features an open concept with a spacious gray sofa adorned with decorative pillows and an orange accent couch. A wooden coffee table occupies the center, while a kitchen with modern appliances is visible in the background. Green plants and framed artwork enhance the inviting space.

4.97 out of 5 average rating, 117 reviews

Stunning Light-filled Home w/HOT TUB walk to town

Standby for photos of our premium upgrades. Spotless home in walking distance to town. Featured in Hudson Valley Style magazine Road Affair's "15 Best Airbnbs in Woodstock" pick 2024. Explore Woodstock & nearby mountains from light-filled 1700 sq ft 1-BR home. Enjoy changing seasons from private patio w/hotub, dining, fire pit & grill 365 days a year. 1st floor fully equipped kitchen, 65" tv, dining room table & desk. 2nd floor bedroom is 800 sq ft & full bathroom & desk 2 dogs w/no fee

4.99 out of 5 average rating, 215 reviews

Cabin in Saugerties

Timberwall Ranger Station | Your Upstate Base Camp

The Timberwall Ranger Station is the perfect home base for your peaceful upstate escape. Located minutes from Woodstock, Saugerties, and Kingston, this breathtaking hand-built cabin is close to all the Catskills and Hudson River Valley have to offer. The cabin is a restful place year-round: for enjoying spring birdsong at breakfast; swaying away an afternoon in a breezy summer hammock; starry skies and luscious wines around an autumn campfire; a cozy winter morning amidst freshly fallen snow.

4.97 out of 5 average rating, 171 reviews

Fall Escape | EV | Hot Tub

The Maverick — A Mid-Century Escape Escape to The Maverick, a beautifully restored 1964 Mid-Century Modern retreat just 5 minutes from downtown Woodstock. Featured in Atomic Ranch and Country Home, this secluded design-forward hideaway blends iconic furnishings, soaring skylights, nature, and indoor-outdoor living. Relax on the expansive decks, explore nearby trails, or unwind in the new 7-person luxury spa hot tub beneath the stars. Come for the design, stay for the experience.

4.98 out of 5 average rating, 147 reviews

Spacious, Private, Close to Town, Work From Home

Spacious, modern ranch-style house on 1.9 acres, atop a hill, with plenty of natural sunlight. Designed and decorated for a relaxing time in Woodstock, the home has an open and flowing layout. Conveniently located minutes from the center of town, it's perfect for those who want convenience to shopping and restaurants. A perfect home for a family getaway, work-from-home alternative or company retreat in the Catskills / Hudson Valley. Outdoor fire pit in the front yard!

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, 541 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, 283 reviews

Modern Escape • Sauna • Firepit • Near Woodstock

Perfect upstate escape! Whether you're planning a romantic couples getaway, a fun trip with friends, a family vacation, or even a much-needed solo escape, The Retro Chic House offers the ideal stay for a memorable local Upstate Experience. This stunning renovated property is designed to cater to a variety of preferences and is guaranteed to provide you with an unforgettable stay. Located 8 mins to Woodstock, 12 mins to Saugerties, & picturesque drive to Hunter!

An open kitchen features exposed wooden beams overhead, with a polished stone countertop and a hanging rack displaying cookware. Glassware is neatly arranged on the shelf above. A dining table with dark wood accents is visible in the foreground, creating an inviting space for meals.

4.89 out of 5 average rating, 545 reviews

Woodstock Historic Artist Estate - The Carriage House

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. Today the former carriage house of the picturesque estate is an architect-renovated gem in an idyllic setting bordering a public preserve, a short walking distance to the center of Woodstock.

4.89 out of 5 average rating, 484 reviews

A well-lit entryway features wooden stairs leading up to a hallway. Light-colored walls and warm wooden flooring create a welcoming atmosphere. A decorative runner rug lies on the steps, and light fixtures above enhance visibility. Doorways at the top of the stairs lead to additional spaces.

Apartment in Woodstock

Nook above the Pub!

1-bedroom, above the historic Woodstock Pub. Full Futon, able to accommodate 3 people. On local and Trailways Bus lines. Walk to shops, restaurants & The Colony. Plenty of hiking trails, skiing, kayaking, music, theatre, etc. Noise from pub below on weekends fluctuates. Bar/restaurant last seating at 9pm Fri/Sat. $10 food voucher, courtesy of your hosts. Twin mattress available on request for extra guest. $25 fee.

LocationHospitality

4.91 out of 5 average rating, 179 reviews

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

Cozy Silo Home with Mountain Views near Woodstock

Escape to the Willow Silo, a unique 3-story tower retreat with stunning mountain views. Comfortably sleeping 6, this charming home is nestled in the woods yet just 10 mins from Woodstock & 15 from Phoenicia. Features include an indoor fireplace, outdoor fire pit, and a deck perfect for stargazing. Your ultimate relaxation getaway awaits, surrounded by hiking trails and nature's beauty. PERMIT No: 23N-277

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 276 reviews

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

Mt. Wonder: Big Cozy Cabin with Wow View

KitchenPetsValue

A refreshing swimming pool is surrounded by a wooden deck adorned with colorful flower pots. Comfortable lounge chairs offer a place to relax under a blue umbrella while a table invites outdoor dining. Lush greenery envelops the area, providing a private and serene setting.

4.9 out of 5 average rating, 212 reviews

HOT TUB on Secluded 7acres, Heated Pool, Stream !

A spacious living room features a large gray sectional sofa paired with a coffee table made of rich wood. Natural light fills the space through multiple windows, highlighting the minimalist decor and a cozy fireplace set against a dark stone wall.

4.99 out of 5 average rating, 154 reviews

Hudson Valley Evergreen Treehouse

The exterior of a timber frame home is showcased, featuring a combination of large windows and wooden siding. A spacious stone patio is visible in front, furnished with chairs and seating areas. Surrounding pine trees and clear blue skies enhance the tranquil setting.

4.95 out of 5 average rating, 256 reviews

Barn Home - Solar! - Music Studio, Views & Hot Tub

4.96 out of 5 average rating, 873 reviews

The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.

Treehouse in Willow

Willow Treehouse - secluded, unique, romantic

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

4.98 out of 5 average rating, 128 reviews

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

A panoramic view of distant mountains stretches under a clear blue sky. The landscape features a mix of trees and open areas, showcasing the natural beauty of the surroundings.

4.88 out of 5 average rating, 153 reviews

Gorgeous Villa Mntn Views • POOL • hot tub •grill!

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

4.99 out of 5 average rating, 277 reviews

The Woodstock Barn House - Sauna, Gym, Jacuzzi

Family- and pet-friendly home rentals

A peaceful outdoor space is presented, featuring a fire pit surrounded by seating chairs on a grassy area. A hammock is seen in the background, providing a cozy spot for relaxation amid lush greenery. The natural setting invites calmness and outdoor enjoyment.

4.91 out of 5 average rating, 535 reviews

Brookside, Walk to Town Center, Dog Friendly

A bright and airy living room features large windows allowing natural light to fill the space. A stylish sectional sofa in warm tones is arranged on a patterned area rug, complemented by a coffee table. Skylights enhance the openness, while artwork decorates the walls.

4.92 out of 5 average rating, 206 reviews

Fabulous Family House nr Woodstock Center

4.86 out of 5 average rating, 271 reviews

The cabin's exterior is characterized by natural wood siding and large glass panels that integrate the structure with its wooded surroundings. A private courtyard with outdoor seating is visible, along with lush greenery and carefully placed stones that enhance the natural landscape.

Cabin in Woodstock

Brand New Modern Cabin walk to town

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

Religious building in Woodstock

1913 Church-History and Magic in the Forest

4.99 out of 5 average rating, 234 reviews

4.97 out of 5 average rating, 173 reviews

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.

Cottage in Saugerties

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

4.84 out of 5 average rating, 229 reviews

The exterior of the barn studio displays a rustic green facade, featuring a prominent gabled window above a set of double doors. A gravel path leads to a grassy yard adorned with potted plants and garden chairs, creating an inviting outdoor space.

Barn in Woodstock

The Woodstock Barn Studio

4.98 out of 5 average rating, 167 reviews

Cabin in Woodstock

Pet Friendly Cabin Doh-Ray in Woodstock

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 129 reviews

Woodstock Family Home w/ Tree House + Heated Pool

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

The interior space showcases exposed timber beams and a warm wood palette. A comfortable seating area is highlighted by a vibrant patchwork rug, while a staircase leads to the upper level. Shelving units display books, and a television is mounted on the wall.

4.99 out of 5 average rating, 378 reviews

Grapevine Cottage

Hospitality

A spacious living area features a hand-built stone fireplace adorned with decorative elements. Large windows allow natural light to fill the room, which includes a dining space with a long table set for guests. Comfortable seating is positioned around the fireplace on a well-defined area rug.

4.96 out of 5 average rating, 113 reviews

MODERN FARMHOUSE in the WOODS

4.91 out of 5 average rating, 117 reviews

Cabin in Kingston

Modern Getaway in Kingston - 1.5hr from NYC

FamilyPoolAccuracy

4.97 out of 5 average rating, 148 reviews

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.

Cottage in Bearsville

Contemporary Guesthouse with Heated Pool

4.9 out of 5 average rating, 140 reviews

An aerial view showcases the spacious home surrounded by trees and a manicured lawn. Outdoor seating is featured on the deck, illuminated by string lights. A fire pit area is visible, enhancing the outdoor gathering space for relaxation and socializing.

Chalet in Ruby

Enchanting Upstate Cabin w Pool, Firepit