Family-friendly holiday rentals in Woodstock

5.0 out of 5 average rating, 463 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

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, 138 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.

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, 279 reviews

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

4.99 out of 5 average rating, 159 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!

The cabin is set amidst lush greenery, featuring a screened porch illuminated by warm lights. Two lounge chairs are positioned on the manicured lawn, with the structure's blue exterior complemented by large windows reflecting the soft hues of sunset.

4.9 out of 5 average rating, 658 reviews

The Pike Lane Cabin & Nature Preserve

The Pike Lane Cabin is nestled in the woods on 7 acres but walking distance to the center of Woodstock. This private retreat offers 2 sleeping areas. The oversized master has a queen bed and its own living area with a queen size sofa bed. The other sleeping area is a full pullout sleeper in the main room. Fully equiped kitchen, full bath, linens, TV, wifi, AC. Four adults allowed plus children 12 or under. Arriving in town early? Come enjoy the grounds or lay in a hammock while you wait until 3.

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!

4.92 out of 5 average rating, 546 reviews

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.

Cottage in Woodstock

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.

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.

4.86 out of 5 average rating, 273 reviews

Brand New Modern Cabin walk to town

This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroom with all new fixtures and a soaking tub. You can walk to town in approximately 10-12 minutes. The distance is .5 mile. ( half mile)This is in a neighborhood so there are visible neighbors but the architect utilized the natural surroundings to make it feel like you are in the woods. The beauty of this house is it’s access to town.

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, 546 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, 488 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.

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

A living room features a leather sofa and a wooden coffee table, surrounded by colorful artwork on the walls. Natural light fills the space through two windows, revealing a warm wood ceiling. A rocking chair and patterned rug add comfort to the inviting atmosphere.

4.98 out of 5 average rating, 256 reviews

Sweeping mountain views in Woodstock, NY

A quick 3 minute drive to the center of town, our recently built 3 bedroom house has gorgeous mountain views and is on 5 beautiful secluded acres surrounded by trees. The property is fantastic in all seasons and close to amazing Catskill skiing, hikes, waterfalls, swimming holes, and the Hudson River, as well as the towns of Phoenicia, Saugerties, Kingston, Catskill, Hudson, Rhinebeck, and Tivoli.

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 174 reviews

Fall Escape | EV | Hot Tub

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, 156 reviews

Hudson Valley Evergreen Treehouse

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, 118 reviews

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

4.93 out of 5 average rating, 277 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

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, 213 reviews

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

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, 258 reviews

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

4.96 out of 5 average rating, 875 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

4.98 out of 5 average rating, 122 reviews

Home in Shokan

Historic Catskills farmhouse with sweeping views

Family- and pet-friendly home rentals

4.85 out of 5 average rating, 302 reviews

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.

Cottage in Woodstock

Woodstock Dog Friendly Cozy Cottage in Town + Yard

4.98 out of 5 average rating, 168 reviews

Pet Friendly Cabin Doh-Ray in Woodstock

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

A light-filled living area features a brown leather sofa and a stylish lamp. The kitchen is visible, with modern cabinetry and a sink, complemented by a small window and potted plant. A colorful artwork adorns the wall, contributing to a welcoming ambiance.

5.0 out of 5 average rating, 101 reviews

Away Upstate, a cozy retreat w/ Firepit

4.87 out of 5 average rating, 1042 reviews

A cozy sleeping area features warm wooden paneling and a spacious bed topped with a striped blanket. A colorful, patterned cushion adds a pop of color. Framed artwork is displayed on the walls, with a warm glow from wall sconces illuminating the space.

Guesthouse in Woodstock

Rocket Room - Rock Stars Only

4.85 out of 5 average rating, 233 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

4.99 out of 5 average rating, 220 reviews

Cabin in Saugerties

Timberwall Ranger Station | Your Upstate Base Camp

4.97 out of 5 average rating, 176 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

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 130 reviews

Woodstock Family Home w/ Tree House + Heated Pool

4.99 out of 5 average rating, 381 reviews

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.

Cottage in Woodstock

Grapevine Cottage

Cabin in Town of Shandaken

Catskills Retreat | Heated Pool & Hot Tub

4.95 out of 5 average rating, 250 reviews

Superhost

A vibrant red exterior wall of the cabin is complemented by neatly arranged flower beds filled with green foliage and orange flowers. A window is visible, reflecting natural light, while gravel pathways lead to the cabin, surrounded by lush greenery.

4.78 out of 5 average rating, 354 reviews

chezbevet-country cabin retreat

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, 154 reviews

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

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

4.9 out of 5 average rating, 144 reviews

Chalet in Ruby

Enchanting Upstate Cabin w Pool, Firepit

An above-ground pool is surrounded by a wooden deck featuring lounge chairs. Lush greenery and trees provide a natural backdrop, while a fenced area with a swing set is visible in the distance, creating a serene outdoor space for relaxation.