Family-friendly holiday rentals in Woodstock

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.

4.99 out of 5 average rating, 149 reviews

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!

KitchenFamilyView

5 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

KitchenFamilyRiver

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, 111 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

KitchenIndoor spacesHiking

4.99 out of 5 average rating, 379 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.

FamilyIndoor spacesAccuracy

4.84 out of 5 average rating, 227 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

Once a Woodstock chicken barn, your space is the lower level which has been renovated as a studio apt. that maintains its rustic charm with wide plank pine floors & ceiling beams. Only 2 blocks (a ten minute walk) to down town Woodstock & the NYC bus stop. We are 1 block from the Tinker St. Cinema and about 1.5 miles from the Bearsville theater. There are hiking trails for you to enjoy, the beautiful Wilson State Park as well as The stunning views of Cooper Lake and the Ashokan Reservoir.

Indoor spacesFamilyWi-Fi

4.98 out of 5 average rating, 164 reviews

Pet Friendly Cabin Doh-Ray in Woodstock

Experience the serenity of the woods and still be close to town. We're on the side of Mt. Guardian just 5 minutes from The Cub Market & 10 minutes from the Village Green. Hike up to the viewpoint from the front door, take a leisurely walk at Cooper Lake, take a dip at a local swimming hole, or just relax on the porch and watch the wildlife stroll by. Visit a cool restaurant in town or in Kingston or just grill & watch a movie with our surround sound system. Bring your pets!

Indoor spacesKitchenView

4.96 out of 5 average rating, 262 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!

FamilyIndoor spacesGetting around

4.96 out of 5 average rating, 278 reviews

Home in Saugerties

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!

FamilyIndoor spacesSleep quality

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.

FamilyIndoor spacesParks

Superhost

Home in Hurley

4.93 out of 5 average rating, 275 reviews

Hot tub with stunning views, 5 min to Woodstock

Enjoy panoramic, unobstructed views of the Ashokan reservoir from our recently updated two story home. Perched on top of Ohayo Mountain we are just 5 minutes drive from the heart of Woodstock Village. The views are as good from the living room as they are from the king bed in the primary bedroom. With multiple outdoor seating areas and a firepit you can make yourself at home both inside and out!

Indoor spacesKitchenBackyard

4.93 out of 5 average rating, 867 reviews

Byrdcliffe Artist Studio (27.1-1-70)

Historic Byrdcliffe Artist's Studio ... is a classic cabin in the woods where theater companies were launched, cartoon characters drawn, and famous books written. Quiet & inspirational, perfect for artists, couples, close friends, and small families. A place to breathe fresh air & see the stars. Everyone is welcome!

FamilyIndoor spacesBackyard

4.99 out of 5 average rating, 373 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

DESCRIPTION Enter our private backyard on 2 1/2 acres by crossing your own bridge far above the forest floor overlooking a stream and waterfall, then meander along a stone path, entering your grape arbor and vegetable garden into your cottage. The gardens where featured in THE Wall Street JOURNAL Sept 11-12 2021

FamilyKitchenLong stay

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

A cabin nestled among tall trees is gently illuminated at dusk. Soft light streams through the open sliding door, revealing a cozy sleeping area with a person resting on a bed. The surrounding forest is lush with greenery, enhancing the serene atmosphere.

4.86 out of 5 average rating, 349 reviews

40-Foot Container Cabin in the Catskills

FamilyIndoor spacesLong stay

4.96 out of 5 average rating, 870 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

KitchenFamilyAccess

4.98 out of 5 average rating, 164 reviews

Fall Escape | EV | Hot Tub

Indoor spacesKitchenBarbecue

The exterior of a modern cabin is showcased, featuring dark wood siding and large windows that invite natural light. A pair of black rocking chairs sits on the deck, complemented by a small metal table and logs stacked nearby. Lush green grass and scattered yellow wildflowers enhance the outdoor setting.

4.97 out of 5 average rating, 183 reviews

Modern Cabin in the Woods with Hot Tub

FamilyIndoor spacesBathroom

4.99 out of 5 average rating, 232 reviews

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 136 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

FamilyIndoor spacesNearby

4.99 out of 5 average rating, 103 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

Indoor spacesFamilyGetting around

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.

4.9 out of 5 average rating, 525 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

FamilyKitchenPool

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 1,081 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

FamilyIndoor spacesBreakfast

The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.

4.91 out of 5 average rating, 777 reviews

Dutch Touch Woodstock Cottage

FamilyIndoor spacesTV

4.83 out of 5 average rating, 132 reviews

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.

Cottage in Woodstock

Woodstock Mountain Cottage w/ Swimming Pool

FamilyKitchenBreakfast

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, 526 reviews

Brookside, Walk to Town Center, Dog Friendly

Indoor spacesFamilyWalkability

4.93 out of 5 average rating, 160 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.

KitchenIndoor spacesComfort

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.

4.96 out of 5 average rating, 211 reviews

Luxury Camping, Northern Moon Cabin

Indoor spacesCheckoutSkiing

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, 265 reviews

Brand New Modern Cabin walk to town

FamilyKitchenCheckout

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, 350 reviews

chezbevet-country cabin retreat

KitchenIndoor spacesView

Family-friendly home rentals with a pool

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.

4.89 out of 5 average rating, 189 reviews

Shula | Farmhouse | Pool, Hot tub, Fire pit

KitchenIndoor spacesAmenities

4.97 out of 5 average rating, 126 reviews

Woodstock Family Home w/ Tree House + Heated Pool

Indoor spacesFamilyAccuracy

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!

KitchenIndoor spacesSleep quality

4.97 out of 5 average rating, 159 reviews

A wooden exterior is complemented by solar panels on the roof, showcasing sustainability. Surrounding foliage displays autumn colors, with trees and shrubs framing the entrance. The home features a welcoming porch area leading to large glass doors that invite guests inside.

Chalet in Mount Tremper

Secluded Woodstock Retreat -Heated Pool and Sauna

Indoor spacesFamilyPool

4.98 out of 5 average rating, 125 reviews

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.

Home in Saugerties

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Indoor spacesFamilyNearby

4.95 out of 5 average rating, 246 reviews

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.

Cabin in Shandaken

Catskills Retreat | Heated Pool & Hot Tub

FamilyKitchenAmenities

5 out of 5 average rating, 172 reviews

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.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

Indoor spacesKitchenRiver