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Family-friendly vacation rentals in Highlands

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Top-rated family-friendly rentals in Highlands

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

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Top guest favorite

The exterior of the modern rustic apartment showcases a wooden structure with a stylish sloped roof. The well-maintained front yard features lush green grass and ornamental plants, while a spacious deck is visible above, complemented by outdoor furniture and shade options.

Guesthouse in Woodstock

5 out of 5 average rating, 379 reviews

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

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" 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

An open living space features warm wooden paneling and large windows, allowing natural light to fill the area. A dining table with woven chairs sits near the center, complemented by a comfortable seating area with plush couches. A wood-burning stove adds character to the room.

Chalet in Tafton

4.85 out of 5 average rating, 131 reviews

Pocono Chalet~HeatedPool~Sauna~Firepits~Fireplaces

This is a one of a kind LINDAL CEDAR HOME, with an open layout, 16 foot Cathedral ceilings with floor to ceiling windows. Perfect getaway for family outings or friends getting out of the city. Following attractions are nearby: Lakes Wallenpaupack Promised Land State Park Skytop Camelback Ski/tube Kalahari Indoor Water Park Mt. Airy Casino NO PROMS NO FRATS POOL opens mid April and closes mid Nov. All guests are required to accept host's lease agreement prior to check in. Pets need approval

Top guest favorite

A spacious retreat is seen from above, featuring a large deck with seating and modern design elements. Surrounding foliage displays vibrant autumn colors, while a gravel pathway leads to the house. The serene landscape emphasizes the property's natural setting.

Home in Round Top

4.96 out of 5 average rating, 196 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Farm stay in Blairstown

4.85 out of 5 average rating, 130 reviews

Cozy LakeView Farm near NYC/Rt.80 & Del. Water Gap

Enjoy Fresh Air & Spacious Views on your retreat w/ a Private Lake, Trails, Fields & Streams throughout. Beauty and Wildlife abounds. Spread out in an open layout apartment. See Guidebook for Seasonal Fun! Escape Pocono traffic & enjoy the countryside. *Close to NYC/Rt 80 thru a Quaint Moravian VIL. Appalachian Trail access. *Animal Tour w/Petting incl. Great local Farms/Markets w/Fresh Food. Alpaca & Wolf Preserve nearby. Hiking nearby. Farm Store coming soon.*3-day all Holidays. 1 dog<40pd.

Top guest favorite

An enclosed porch features two metal-framed chairs with cushions, positioned near a small table. A decorative rug with vibrant floral patterns covers the floor. A potted plant and a lantern add to the decor, with sunlight streaming through the windows overlooking the water.

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Home in Bushkill

4.93 out of 5 average rating, 137 reviews

POOL, Game Room, Lakefront, Hot Tub, PickleBall

Olibear is your ultimate spring retreat—ideal for couples, families, or anyone seeking a lakefront escape. Nestled by the water, our home offers warm charm amid blooming Pocono landscapes. Just 5 minutes from Bushkill Falls, explore vibrant spring or relax by the indoor community pool, open weekends 12-4 PM Enjoy the private hot tub, paddle kayaks or canoes, explore vibrant trails, or relax by the firepit under the spring sky. Indoor pool open on weekends Claim your spring escape now!

A charming two-story house features a welcoming porch bordered by colorful flower beds. Blue trim accents the white exterior, highlighting the architectural details. A pathway leads to the entrance, which is framed by a decorative arch and supported by columns.

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Townhouse in East Stroudsburg

4.95 out of 5 average rating, 240 reviews

White Tail House-Hiking, Biking & River adventure

Our house is located just up the road from the Shawnee Mountain Ski Area. Located between Bushkill Falls and the Delaware National Recreation Area offers hiking, biking, rivers, streams, and waterfalls. From Spring to Fall, easy access to kayak or canoe rentals. Numerous golf courses are just minutes away. The historical town of Delaware Water Gap and Stroudsburg offers a variety of restaurants, music venues, wineries, and boutiques. Best of all, we are only 75 minutes west of NYC.

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

4.95 out of 5 average rating, 355 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

A charming children's playroom features a wooden playhouse adorned with colorful decorations. Beside it, a round table with two red chairs offers a space for creative play. A light blue pouf and a basket filled with plush toys add to the playful atmosphere, illuminated by a teal lamp.

Chalet in East Stroudsburg

4.92 out of 5 average rating, 435 reviews

Cozy House - Lovely Fairytale TreeHouse - Hot Tub

Experience a nature lover's paradise in this stunning house with serene surroundings for play and relaxation. Perfect for families, it sleeps up to 6 adults and features a spacious living room, entertainment loft, and a 7-person hot tub for post-exploration relaxation. With its prime location, you're close to major Pocono Mountains attractions like Camelback Water Parks, Crossing Outlets, Delaware Water Gap, and more—the ultimate destination to explore this scenic region.

A cabin is shown nestled among trees, with a wooden deck overlooking a gently flowing stream. Vibrant autumn leaves contrast against the dark exterior of the cabin, enhancing the natural setting. The scene captures the peacefulness of the surrounding landscape, inviting relaxation.

Cabin in Accord

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Home in Palenville

4.96 out of 5 average rating, 164 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

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Popular amenities for Highlands family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in East Stroudsburg

4.92 out of 5 average rating, 189 reviews

Big House On The Hill - Hot Tub, Sauna, Fireplace!

Home in Rhinebeck

4.91 out of 5 average rating, 232 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

A bright living area features large windows that allow natural light to illuminate a pink sectional sofa adorned with colorful cushions. A white coffee table sits atop a light wooden floor, complemented by a decorative rug. Art pieces in warm hues are displayed on the wall.

Home in Olivebridge

4.92 out of 5 average rating, 455 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

The kitchen features an open layout with bright natural light illuminating modern appliances, a spacious island with seating, and rustic shelving displaying various kitchen essentials. A solid wood dining table sits in the background, complemented by a patterned rug beneath.

Chalet in Jewett

4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

A bright living area features expansive floor-to-ceiling windows offering views of the autumn foliage outside. Comfortable seating includes a green sofa and modern chairs. A textured area rug and a decorative coffee table complete the space, enhancing a warm and inviting atmosphere.

Cabin in Swan Lake

4.83 out of 5 average rating, 201 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

A hot tub is illuminated with soft blue light, situated on a deck. Snow-covered ground surrounds the area, providing a tranquil setting in the evening. The hot tub features a spacious design, accommodating several guests for relaxation.

Cabin in Bushkill

4.9 out of 5 average rating, 188 reviews

Bushkill Falls Cabin

The open-plan living space features large windows offering expansive views of the rolling farmland. A comfortable gray sofa faces a wooden coffee table, while a modern TV stand holds a flat-screen television. The adjacent kitchen includes barstools at a countertop with navy cabinetry.

Cottage in North Branch

4.94 out of 5 average rating, 133 reviews

Renovated Country Cottage w/ Hot Tub & View

The charming country house showcases a light-colored exterior with symmetrical windows and a covered porch. Lush greenery surrounds the entryway, providing a welcoming feel. The roof features a gabled design, and a garage is positioned on the left side of the image.

Home in Elizaville

4.86 out of 5 average rating, 101 reviews

Peaceful Hudson Valley Retreat House with HOT TUB!

Family- and pet-friendly home rentals

The modern barn-style home is surrounded by lush greenery, featuring large windows that highlight its spacious interior. A wraparound deck with railings invites outdoor relaxation, while an inviting facade includes a prominent gabled entry. Soft lighting enhances the welcoming ambiance as dusk approaches.

Home in Mount Tremper

4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Top guest favorite

The two-story home features a red-brick facade with white trim and a covered front porch supported by white columns. A seasonal decoration with a pumpkin is visible on the porch. Large windows allow natural light, and the surrounding yard displays green grass and trees.

Home in Saugerties

4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

A scenic lakeside area features a wooden deck with seating made of natural tree stumps, complemented by a green umbrella for shade. A kayak is visible nearby on the water, with lush greenery framing the tranquil lake view.

Home in Ulster Park

4.88 out of 5 average rating, 227 reviews

Entire lake house to yourself. Great for groups

A charming wooden house is set among trees with green leaves and a gently landscaped pathway. Warm light emanates from the windows, illuminating the porch area. The seasonal fallen leaves create a natural carpet on the ground, enhancing the serene woodland surroundings.

Cabin in Woodstock

4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

Top guest favorite

The living room features a dark sofa adorned with cushions, complemented by a light-toned area rug. A mid-century chair with a soft throw and a glass coffee table enhance the cozy ambiance. Green plants bring a touch of nature, while large windows allow ample natural light.

Apartment in Clinton Hill

4.98 out of 5 average rating, 118 reviews

Family brownstone with backyard

A fenced backyard is visible, featuring a grassy area with a decorative lantern hanging from a tree. Two chairs are placed on the lawn, and a stone path leads towards the rear of the property, where a raised deck is positioned.

Vacation home in Hudson

4.9 out of 5 average rating, 122 reviews

2 blocks to Warren ST w/ a yard and parking

Home in West Kill

4.93 out of 5 average rating, 121 reviews

Catskill Mountain Cabin Waterfall Retreat

A person is paddling on a calm, reflective pond surrounded by lush greenery and hills in the background. The water's surface mirrors the landscape, enhancing a serene atmosphere. The scene is framed by trees and a gently sloping area, showcasing nature's beauty.

Cabin in Prattsville

4.83 out of 5 average rating, 169 reviews

Private Waterfront w/Swimming, Boats & Hot Tub!

Family-friendly home rentals with a pool

Top guest favorite

The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.

4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

A welcoming seating area is presented, featuring two comfortable chairs, a side table, and a vibrant accent chair. A blue cabinet filled with decorative items sits against the wall, while a colorful wall art piece and a patterned floor add visual interest. Natural light streams through the entry door.

Cottage in West Orange

4.87 out of 5 average rating, 204 reviews

Cozy Pool Cottage

A modern farmhouse exterior is visible beside a crystal-clear swimming pool surrounded by grassy areas. Colorful pool floats are placed in the water, while a wooden fence and tall trees frame the peaceful setting.

Home in Saugerties

4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

Home in Englewood

4.93 out of 5 average rating, 153 reviews

Englewood NJ Country Carriage House (15 min NYC)

A large heated swimming pool is surrounded by lush greenery, with several lounge chairs arranged on a concrete deck. A float in blue and white lies on the water's surface, and an umbrella provides shade nearby.

Apartment in Saugerties

4.97 out of 5 average rating, 111 reviews

Lovely Creekside w pool/sauna near Woodstock

A wooden deck is featured, equipped with a patio umbrella, overlooking a seasonal swimming pool. Surrounding trees provide privacy and a natural setting. A gravel pathway leads to the cabin, enhancing the serene ambiance of the forested area.

Cabin in East Stroudsburg

4.88 out of 5 average rating, 129 reviews

Pocono cabin with POOL at Shawnee Mtn

A serene salt-water pool reflects the surrounding greenery and blue sky. The natural stone edge frames the pool, while two lounge chairs are positioned nearby, creating a peaceful outdoor retreat.

Home in Cold Spring

4.95 out of 5 average rating, 167 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

A clear, blue saltwater swimming pool is surrounded by lush greenery and tall trees. Lounge chairs are positioned by the poolside, with a stone path leading to the water. The tranquil setting provides a sense of privacy and relaxation.

4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

Quick stats about vacation rentals that are family-friendly in Highlands

Total rentals
130 properties
Nightly prices starting at
G$25,255 GYD before taxes and fees
Total number of reviews
6.6K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore