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, 133 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, 457 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, 155 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.

4.98 out of 5 average rating, 114 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, 382 reviews

A modern tiny house is framed by lush greenery, featuring a wooden exterior and large windows that invite natural light. A spacious deck with a full-size dining table is visible, surrounded by a well-maintained landscape of plants and grass.

Tiny home in Saugerties

Modern Catskills Cabin

SISTER PROPERTY OF 5-STAR RATED, COZY CATSKILLS CABIN (ALSO IN SAUGERTIES): 10 minutes from the charming towns of Saugerties and Woodstock, this super-cozy, Tonga has every modern convenience, overflows with style, and comfortably sleeps up to four. The tiny house/cabin feels a million miles away, yet is close to area restaurants, breweries, music venues, ski resorts and other attractions. Think of it as the perfect private getaway with creature comforts aplenty and lots of peace and quiet.

4.83 out of 5 average rating, 221 reviews

The charming green cottage is surrounded by lush trees and landscaped gardens. A stone pathway leads to the entrance, and several shrubs have been planted alongside the path, enhancing the natural setting. Soft grass covers the area in front of the house.

Cabin in Bearsville

The CubHouse NEW Barrel Sauna at foot of Mountain

WOODSTOCK/BEARSVILLE Escape to a little healing magic in this 1909 built cottage. Originally owned by a medicine woman in the early 1900s. This home has charm(s) of an enchanted past and it has been renovated to provide a modern, cozy experience. -Wood burning fireplace -Projector w/screens inside & in screenhouse -Full kitchen -River and Mountain access -Propane grill -500 sq ft screen house (closed during winter months) Dog friendly but must be approved before booking. $25 per night fee

4.93 out of 5 average rating, 164 reviews

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.

Cottage in Woodstock

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).

4.98 out of 5 average rating, 168 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.

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, 532 reviews

Brookside, Walk to Town Center, Dog Friendly

Perfect Catskills basecamp! Three-bedroom getaway an 8-minute stroll to Woodstock’s shop and restaurants yet tucked beside a babbling brook. Why guests love it: • Bright living room with huge couch for cozy fireplace moments with friends and family • Ultra-fast Wi-Fi for work or play (3 desks) • Dog-friendly & fully stocked kitchen • Fire pit • Connected to nature As Superhosts we are committed to keeping the home spotless. Just press the reserve button and relax :)

4.91 out of 5 average rating, 537 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.

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.

4.9 out of 5 average rating, 178 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, 273 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

4.96 out of 5 average rating, 872 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

Superhost

A serene view of expansive mountains is captured under a clear blue sky, complemented by lush greenery in the foreground. A variety of trees and a rural landscape with a distant red barn can be seen, creating a peaceful natural setting.

4.91 out of 5 average rating, 528 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

A spacious outdoor dining area features a long wooden table set with plates, wine glasses, and food, surrounded by nature. In the background, a wooden cottage is visible, framed by trees. A cozy fire pit with Adirondack chairs adds to the inviting atmosphere.

4.9 out of 5 average rating, 480 reviews

Hot Tub, Fire Pit, Fully-Fenced Yard, Pellet Stove

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!

A scenic view of a two-story cottage surrounded by lush greenery. The well-maintained garden features various plants and flowers. A fenced yard offers a sense of privacy, with a pathway leading to the entrance. The structure displays a blend of traditional and modern architectural elements.

4.93 out of 5 average rating, 989 reviews

1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole

4.99 out of 5 average rating, 232 reviews

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

4.93 out of 5 average rating, 278 reviews

Home in Hurley

Hot tub with stunning views, 5 min to Woodstock

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 213 reviews

Cabin in Saugerties

Timberwall Ranger Station | Your Upstate Base Camp

4.86 out of 5 average rating, 269 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

4.84 out of 5 average rating, 228 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, 574 reviews

The interior features exposed wooden beams and walls, with a warm wooden floor. A cozy living area accommodates a dark sofa and a fireplace. A dining table with four chairs is positioned nearby, and large glass doors provide access to outdoor views.

Cabin in Boiceville

Winston's Place - Woodland Cozy Catskills Cabin

4.88 out of 5 average rating, 1088 reviews

An exterior view of an old milk barn, featuring a wooden door and overgrown greenery surrounding the structure. The rustic charm is highlighted by exposed brick and an angled roof. A few outdoor furniture pieces are positioned nearby, complementing the natural setting.

Farm stay in High Falls

Dave's Milk Barn

4.96 out of 5 average rating, 212 reviews

A cozy bedroom features large windows framed by dark curtains, allowing natural light to illuminate the space. A spacious bed with soft pillows and a comfortable blanket is positioned against a light-colored wall. A small table is visible in the foreground.

Cabin in Saugerties

Luxury Camping, Northern Moon Cabin

4.98 out of 5 average rating, 166 reviews

Cabin in Woodstock

Pet Friendly Cabin Doh-Ray in Woodstock

4.78 out of 5 average rating, 352 reviews

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.

Cabin in Woodstock

chezbevet-country cabin retreat

Family-friendly home rentals with a pool

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

4.93 out of 5 average rating, 121 reviews

Summer Paradise - Pool, Fire-pit, Nursery!

4.99 out of 5 average rating, 374 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

4.97 out of 5 average rating, 146 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

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

5.0 out of 5 average rating, 172 reviews

Upstate Modern Scandinavian Barn in the Catskills

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 !

4.97 out of 5 average rating, 172 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

Cabin in Town of Shandaken

A seasonal saltwater pool is surrounded by a wooden deck and lounge chairs, offering a scenic view of the lush hillside. An umbrella provides shade, and a basketball hoop is positioned at one end of the pool, enhancing outdoor leisure options.

4.95 out of 5 average rating, 247 reviews

Catskills Retreat | Heated Pool & Hot Tub

Superhost

A tranquil saltwater pool is set against a natural stone backdrop, surrounded by lush greenery. Poolside, a sunbed and umbrella are positioned, providing a relaxation spot. The patio features a rugged stone surface, enhancing the outdoor experience amidst a serene atmosphere.