Family-friendly vacation rentals in Highlands

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Highlands family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A two-story red cottage is nestled among tall trees, showcasing a classic design with multiple windows and balconies. A gravel driveway leads to the entrance, providing access to outdoor spaces. The surrounding wooded landscape adds to the cottage's natural setting.
Home in Bearsville
4.92 out of 5 average rating, 230 reviews

A Cozy’s Woodstock Getaway Home

ClancyRating, 5 stars3 weeks ago
This space is so lovely, the hot tub worked perfectly and provided many cozy nights outside. The plants are BEAUTIFULLY tender and bring a loving atmosphere to the space. the linen sheets were so wonderful at the end of the day. we made it up the hill in a Honda insight, but if it were a tiny bit icy I don't think we would have been able to make it. definitely use 4wd if you have it. the hosts were very responsive. if the noise is too much in the bedroom at night (critters, rain,etc.) be sure to use the fan they provide, it helped us a lot :) the kitchen was a delight to use. sharp knives. big, metal surfaces. nice gas stove. big fridge.
Superhost
A bright living area is furnished with a comfortable dark sofa adorned with colorful cushions, a wooden coffee table, and a black armchair. Natural light floods the space through large windows, highlighting the open kitchen and dining area with clean lines and warm wooden accents.
Home in Woodstock
4.84 out of 5 average rating, 110 reviews

2 BR , Fireplace & Hot Tub @ heart of Woodstock

AndrewRating, 5 stars2 months ago
We had a wonderful time at Mirav’s place in Woodstock. Made great use of the hot tub and the fireplace. We absolutely plan on returning soon!
Guest favorite
A year-round hot tub is situated on a wooden deck, surrounded by trees. Adjacent to the deck, a screened porch features a dining table and chairs, inviting outdoor relaxation. Soft sunlight filters through the foliage, enhancing the natural setting.
Home in Bearsville
4.92 out of 5 average rating, 134 reviews

Secluded Artist's Retreat with Hot tub

DavidRating, 5 stars4 months ago
We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!
Top guest favorite
Home in Rhinebeck
4.91 out of 5 average rating, 230 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

AudreyRating, 5 stars1 month ago
Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!
Superhost
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

LindsayRating, 5 stars2 weeks ago
We had such a nice stay in Olivebridge. Wray’s home is beautifully decorated and extremely private, and just a half hour drive to Woodstock, where there are plenty of shops and restaurants to explore. The hot tub was a bonus, as was the very eclectic DVD collection. Highly recommend! Thanks again for having us!
Superhost
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

CarolineRating, 5 stars3 weeks ago
Our group had a great time at Anna’s place. Spacious and comfortable with great views. Anna is very responsive and gave clear check in instructions. Little communication needed given her detailed instructions, and the little communication needed- she was very responsive.
Superhost
A modern two-story home is surrounded by a lush green landscape and tall evergreens. The exterior features light-colored siding, large windows, and a welcoming front porch with white railings. A decorative stone wall lines the front yard, enhancing the natural beauty of the setting.
Home in Chichester
4.87 out of 5 average rating, 141 reviews

Make it your home away from home

HungRating, 5 stars2 months ago
I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!
Guest favorite
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

AndreRating, 5 stars1 month ago
Gorgeous house, super clean and tidy inside, with comfy and modern furniture. The hot tub was fantastic, make sure you turn off the lights so you can see the stars! The only other heads up I’ll give is that the way to get in is through the back entrance! We tried the front door for like 5 minutes until the electronic lock blocked us from continuing haha. Great location to get away from the city for a weekend and go hiking. Lots of great trails really close by.

Family- and pet-friendly home rentals

Guest favorite
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

Tracy,JRating, 5 stars2 weeks ago
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.
Guest favorite
A dining area is featured with a light wood table surrounded by colorful chairs in red and blue. A shelf on the adjacent wall displays decorative items and books, while sunlight illuminates the inviting wooden floor.
Cottage in Willow
4.86 out of 5 average rating, 250 reviews

Peace Cottage

SarahRating, 5 stars1 month ago
I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.
Guest favorite
A historic two-story family home is set on manicured grass, displaying large windows and a welcoming red front door. The structure is surrounded by lush trees, contributing to the tranquil outdoor setting. The home's classic architecture reflects its rich history.
Home in Milton
4.75 out of 5 average rating, 178 reviews

Historic 1 BR Family Home Near Buttermilk Falls

DianeRating, 5 stars1 week ago
What a perfect place to stay! We were very comfortable in Hazel’s little retreat… we slept well in the king sized bed, had plenty of hot water, loved the bucolic green space and the creek nearby. Our dogs had great walks under the canopy of huge trees surrounding the property. I especially enjoyed watching and hearing the ducks, geese and swans across the street as they paddled to the pond! Thank you, Hunter for providing a perfect getaway spot for your guests!
Superhost
The exterior of the cottage is surrounded by lush greenery and trees, creating a serene atmosphere. Windows with charming details are visible, along with a fenced area. A pathway leads to the entrance, which features blue doors and a welcoming entry.
Cottage in Woodstock
4.84 out of 5 average rating, 146 reviews

Rock City Writer's Studio: bucolic•sauna•walkable!

AdaRating, 5 stars2 weeks ago
Super close to town! Lovely setting. Fun to take a shower under a skylight. As others have said, it’s very compact! Would be an ideal place for a person to get away to write.
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!

OrionRating, 5 stars3 months ago
Lovely place in Saugerties, close to lots of great hiking and restaurants.
Superhost
A two-story yellow house is observed from the front. The structure features a wooden porch with white railings and a central door. Windows are symmetrically arranged, providing a welcoming appearance. The surrounding area includes electric lines and a paved street.
Home in Wallkill
4.88 out of 5 average rating, 168 reviews

Wallkill Inn

KeishaRating, 5 stars1 month ago
This house was nice, steap stars. one hour away from all three locations JW branches.
Superhost
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

Maggie FuentesRating, 5 stars5 days ago
Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!
Guest favorite
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

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

Family-friendly home rentals with a pool

Top guest favorite
An open-concept living area is showcased, featuring a spacious sectional couch adorned with colorful cushions. A wooden bookshelf lines one wall, while large windows invite natural light and views. The modern kitchen is visible in the background, complemented by a clean design and simple decor.
Home in New Paltz
4.98 out of 5 average rating, 482 reviews

midcentury mod * POOL * walk out trail to mohonk

TaraRating, 5 stars3 weeks ago
Susan’s home is wonderful. The layout of the house was perfect. We had my elderly parents with us and we did not feel at all as if we were on top of each other. The kitchen was also perfect for a small group to entertain and was loaded with amenities! Everything was spotless and exceptionally clean. It’s very close of the village of New Paltz (3 min. car ride) where the restaurants and shopping is located. We also had a nice view of Mohonk Mountain! All in all it was a perfect and peaceful getaway weekend in the mountains!
Top guest favorite
A spacious backyard is highlighted, featuring a volleyball net between two trees and a hammock hanging nearby. Sunlight filters through the leaves of the surrounding trees, illuminating the well-maintained grassy area. A small shed is visible in the background, offering additional outdoor storage.
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 months ago
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!
Guest favorite
A cozy living area features a light-colored couch adorned with decorative pillows. An armchair sits next to a window, allowing natural light to illuminate the space. Framed art hangs on the walls, complemented by a colorful area rug and a small wooden coffee table.
Home in Saugerties
4.94 out of 5 average rating, 139 reviews

5BR close to Village | Diamond Mills | HITS | Pool

SheillaRating, 5 stars3 months ago
Overall the place was very nice to stay at. Hosts/Property manager were EXCELLENT communicators (we had an issues and they had solutions within 30 minutes). Close to supermarket (right down the street), along with close to being downtown Saugerties, resturants and getting on the thruway. Would recommend for families.
Guest favorite
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

EricaRating, 5 stars2 weeks ago
My stay here has been made so comfortable, the local was perfect for my stay. Quiet and all supplies provided for our stay. Micaela is very responsive and I’m grateful to have found this cozy location right here in West Orange. Close to supermarkets, jitney to the train, movie theater, turtle back zoo and more. A great getaway for anyone who needs a break or home for a few weeks. Thank you Micaela.
Top guest favorite
The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.
Cabin in Red Hook
4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars5 days ago
Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.
Guest favorite
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

BenjaminRating, 5 stars6 months ago
We had a terrific stay. The house was exactly as advertised.
Superhost
A spacious living area features a large sectional sofa in deep blue, positioned adjacent to a wooden dining table that accommodates multiple guests. Natural light fills the room, enhanced by a decorative plant in the corner, creating a welcoming environment.
Home in Bushkill
4.84 out of 5 average rating, 141 reviews

FREE Amenity Passes Spacious Sauna Lrg Deck Firepi

TasheikaRating, 5 stars2 months ago
Our stay at this property was nothing short of excellent! From the moment we arrived, we were impressed by the beautiful ambiance and attention to detail throughout the home. Every room was comfortable, well-appointed, and loved by everyone in our group. The property was clean, inviting, and had everything we needed for a relaxing getaway. The host was responsive and accommodating, ensuring our stay was seamless. We truly enjoyed every moment and would highly recommend this Airbnb to anyone looking for a fantastic place to stay. We can’t wait to return!
Guest favorite
Home in Englewood
4.93 out of 5 average rating, 153 reviews

Englewood NJ Country Carriage House (15 min NYC)

VirginiaRating, 5 stars1 week ago
This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

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

  • Total rentals

    130 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 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