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Family-friendly holiday rentals in Zena

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Top-rated family-friendly rentals in Zena

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
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.
Home in Woodstock

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, 279 reviews
Top Guest favourite
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!

4.99 out of 5 average rating, 159 reviews
Top Guest favourite
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

5.0 out of 5 average rating, 464 reviews
Top Guest favourite
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.

4.99 out of 5 average rating, 221 reviews
Top Guest favourite
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.
Home in Saugerties

Away Upstate, a cozy retreat w/ Firepit

The Away Upstate retreat is nestled in the breathtaking Catskills and is your perfect home away from home year-round. Whether you’re planning a couples getaway, a trip with friends, a family vacation, or a solo escape, our retreat is a perfect place to create lasting memories. Share stories around the outdoor firepit, cozy up by the woodstove or read a book on the hammock. Located: 5 mins from Woodstock 10 mins from Saugerties 15 mins from Kingston 30 mins from Hunter Mtn. @awayupstate

5.0 out of 5 average rating, 102 reviews
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.
Home in Woodstock

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

4.9 out of 5 average rating, 532 reviews
Top Guest favourite
Home in Woodstock

Woodstock Family Home w/ Tree House + Heated Pool

Town of Woodstock Special Use (aka STR) Permit #23-0683. Featured in Hudson Valley Style Magazine, this fully updated modern farmhouse is ready to host. Radiant-heated full baths, whole-house generator, PRIVATE heated saltwater pool (schedule/weather permitting), four-season porch, indoor fireplace, fully equipped kitchen, outdoor grill, etc. Basement includes ping pong and pool tables. All bedrooms and full baths upstairs. Half bath on the main floor. Dogs are not permitted at any time.

4.97 out of 5 average rating, 130 reviews
Top Guest favourite
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.
Home in Saugerties

Hudson Valley Evergreen Treehouse

Welcome to our new Scandinavian designed 5 bedroom, 3 bath treehouse in the Hudson Valley. Experience a relaxing nature setting w/mountain view, 6 min. drive to downtown Woodstock, launchpad to Hunter, Belleayre, nearby wineries & hiking trails. The house offers a private setting, borders a nature preserve, & features a chef's kitchen, living room w/fireplace, cathedral ceilings, wrap around deck, screened in porch, new jacuzzi spa, large movie room, pool table, ping pong table, & more.

4.99 out of 5 average rating, 157 reviews
Top Guest favourite
A single-story red house is set amidst lush greenery, featuring a well-maintained lawn. Large windows provide views of the surrounding trees. The property includes a deck and is situated in a quiet, spacious area.
Apartment in Woodstock

Redbird 1926

A charming one 1 BR apartment attached to our home with a private deck. Entrance to deck and apt. is up eight stairs. Located in a quiet country setting 5 min. from the center of Woodstock and 15 min. from Kingston. This lovely apt. includes central A/C, WiFi, Roku, refrig., outdoor gas grill, microwave, toaster, coffee maker, sink, counter top electric burners, no oven. The bedroom has queen size bed. LR has a day bed for added sleeping space. Come spend time in a tranquil setting.

4.99 out of 5 average rating, 191 reviews
Guest favourite
A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.
Home in Woodstock

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

4.96 out of 5 average rating, 185 reviews
Guest favourite
Guest suite in Woodstock

The Carriage House: Garden Apartment

We offer a private apartment located on the first floor of this wonderfully restored 2 unit carriage house, built in the early roarin' 20's! It offers a blend of modern decor and amenities, with more traditional countryside accents. The design, using the original carriage doors in the architecture, allows light to pour through the apartment, while making adjustments for sleeping in easy. This truly unique space is a perfect place to take a weekend to relax, and even enjoy our grounds!

4.83 out of 5 average rating, 570 reviews
Guest favourite
Guest suite in Woodstock

Woodstock Private Suite: Ensuite Bath & Patio

Spacious and flooded with daylight, this spacious room has a comfortable king sized bed and a roomy ensuite bathroom. Two sets of sliding patio doors let in lots of daylight and lead out to your patio space and a backyard. You'll enjoy a picturesque view of trees and wildlife. The suite is situated on the ground/lower level of my home and is a peaceful and comfortable spot to land. It's located on a quiet tree lined residential street 2 1/2 miles away from Woodstock's center.

4.83 out of 5 average rating, 227 reviews

Popular amenities for Zena family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
Home in Woodstock

Fall Escape | EV | Hot Tub

4.97 out of 5 average rating, 174 reviews
Top Guest favourite
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.
Home in Saugerties

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

4.95 out of 5 average rating, 259 reviews
Top Guest favourite
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

4.98 out of 5 average rating, 129 reviews
Top Guest favourite
Home in Shokan

Historic Catskills farmhouse with sweeping views

4.98 out of 5 average rating, 122 reviews
Top Guest favourite
Home in Saugerties

Private Hot Tub | Firepit | EV| Garden | Patio BBQ

5.0 out of 5 average rating, 252 reviews
Guest favourite
A spacious hot tub sits by the tranquil waterfront, with serene views of the creek and surrounding trees. Adirondack chairs are positioned nearby, inviting relaxation under clear blue skies.
Home in Lake Katrine

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

4.95 out of 5 average rating, 109 reviews
Top Guest favourite
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

5.0 out of 5 average rating, 173 reviews
Top Guest favourite
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.
Home in Woodstock

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

4.97 out of 5 average rating, 118 reviews

Family- and pet-friendly home rentals

Top Guest favourite
Cabin in Woodstock

Byrdcliffe Artist Studio (27.1-1-70)

4.93 out of 5 average rating, 888 reviews
Guest favourite
The spacious studio features a large bed with a teal blanket, complemented by colorful wall art and warm wooden flooring. Natural light enters through a skylight and large windows dressed with sheer curtains. A flat-screen TV and a small refrigerator are positioned nearby.
Loft in West Hurley

Woodstock Chalet - Peace & Quiet & Space (O my!)

4.89 out of 5 average rating, 157 reviews
Top Guest favourite
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.
Cabin in Woodstock

The Pike Lane Cabin & Nature Preserve

4.9 out of 5 average rating, 659 reviews
Top Guest favourite
A cabin is nestled among lush greenery, featuring a simple wooden porch with a small table and two chairs. The exterior is finished in earthy tones, with a sloped roof and large windows, providing ample natural light. The surrounding area is serene, with trees and vegetation.
Cabin in Kingston

WoodsCabin/Kingston/woodstock NY.

4.95 out of 5 average rating, 110 reviews
Guest favourite
A bright sunroom features a comfortable seating area adorned with patterned cushions. Large windows allow natural light to fill the space, complemented by a small lamp and a decorative rug with a floral design. A propane stove adds warmth, while potted plants bring a touch of nature inside.
Home in Woodstock

Architect's Farmhouse in Woodstock

4.89 out of 5 average rating, 203 reviews
Top Guest favourite
A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.
Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

4.94 out of 5 average rating, 375 reviews
Guest favourite
Cottage in Woodstock

Romantic luxury+stream+walk to town=Brook Cottage

4.93 out of 5 average rating, 153 reviews
Top Guest favourite
A modern A-frame cabin is positioned among vibrant autumn foliage. The exterior features large triangular windows framed by wood, and a spacious deck surrounds the front. A stacked log wall is visible beneath the deck, creating a natural aesthetic against the landscape.
Cabin in Saugerties

Stunning 2-Bedroom A-Frame in the Woods with Sauna

4.98 out of 5 average rating, 298 reviews

Family-friendly home rentals with a pool

Guest favourite
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.
Home in Saugerties

Chef’s Kitchen * Screened Porch * Near Woodstock

4.93 out of 5 average rating, 126 reviews
Guest favourite
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.
Home in Saugerties

MODERN FARMHOUSE in the WOODS

4.96 out of 5 average rating, 114 reviews
Superhost
Chalet in Ruby

Enchanting Upstate Cabin w Pool, Firepit

4.89 out of 5 average rating, 145 reviews
Guest favourite
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

4.97 out of 5 average rating, 176 reviews
Guest favourite
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 Sunset Mountain Cottage Fall Hikes

4.83 out of 5 average rating, 133 reviews
Top Guest favourite
A spacious country house is showcased with a large wraparound deck featuring an umbrella and seating. The well-maintained grounds include greenery and a glimpse of an above-ground pool in the background, complemented by a clear blue sky.
Home in Saugerties

Peaceful Hudson Valley Getaway

4.93 out of 5 average rating, 129 reviews
Top Guest favourite
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.
Home in Woodstock

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

4.88 out of 5 average rating, 155 reviews
Top Guest favourite
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

4.99 out of 5 average rating, 382 reviews

Destinations to explore