Family-friendly vacation rentals in Monticello

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Monticello family-friendly rentals

Family-friendly home rentals with a hot tub

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, 458 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

AmeliaRating, 5 stars1 month ago
We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!
Top guest favorite
The lakehouse is nestled among tall trees, with a spacious deck overlooking the water. Colorful flowers enhance the natural landscape, while a rocky shoreline leads to tranquil waters. Sunlight filters through the trees, creating dappled patterns on the house and surroundings.
Cottage in Highland Lakes
4.97 out of 5 average rating, 329 reviews

The Mountaintop Lakehouse that Time Forgot.

YekaterinaRating, 5 stars5 days ago
We had a great time fishing and going to local farms! The hosts were great! They even got us some night crawlers and helped find a hat we left & ship it back!
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, 135 reviews

Renovated Country Cottage w/ Hot Tub & View

DennisRating, 5 stars2 days ago
This was a nice AirBnB for the area, cozy and felt somewhat secluded despite being viewable from the main road. Perfect for a small dog to roam around on the grassy area, and the hot tub looking out into the back was a nice touch and enjoyable to sit in. We were looking for a relatively short get away from the city, quiet and close enough to things in the area to enjoy, and this fit the bill perfectly. The house was very clean with very clear instructions, and nice touches that made it feel cozy. Highly recommend for 2-4 people, particularly with small dogs.
Superhost
The exterior of a log cabin is showcased, surrounded by lush greenery. Solar panels adorn the roof, and an American flag is displayed by the entrance. A manicured lawn extends in front, creating a welcoming first impression of the secluded retreat.
Cabin in Roscoe
4.93 out of 5 average rating, 228 reviews

Roscoe Retreat

OlkaRating, 5 stars1 day ago
beautiful place, friendly owners, everything you need to disconnect from a crazy world
Guest favorite
A spacious living area is furnished with a large sectional sofa, adorned with decorative throw pillows. Natural light filters through multiple tall windows, illuminating a central coffee table accompanied by simple decor. In the background, a large dining table and green accents enhance the inviting atmosphere.
Home in High Falls
4.95 out of 5 average rating, 219 reviews

Clove Schoolhouse on Mohonk Preserve

PaulRating, 5 stars1 week ago
We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.
Superhost
A cabin exterior features large glass windows revealing a cozy sleeping area adorned with soft bedding. A pendant light illuminates the space, offering a warm glow. Lush greenery and colorful flowers line the path leading to the cabin, enhancing the natural setting.
Cabin in Saugerties
4.81 out of 5 average rating, 265 reviews

Container Cabin in the Catskills (Field)

NoraRating, 5 stars1 week ago
Beautiful inside and out — a peaceful oasis & retreat from everything! Nearby restaurants and hikes but also so quiet and private. Great weekend we will be back!!
Guest favorite
The serene Neversink River reflects the surrounding landscape, featuring a still surface that mirrors the clouds above. A weathered log extends from the shoreline into the water, framed by lush greenery and rolling hills in the background.
Home in Neversink
4.98 out of 5 average rating, 218 reviews

Modern Riverside Retreat with Firepit, Hot tub

TracRating, 5 stars4 months ago
The house is spacious and elegant. The wooded lot has a pretty creek a little way from the house. We took some walks through the snowy woods and roads beyond the house and could have kept going for a long time - the mountain is peaceful and beautiful. The owners live a few doors down and came by to help set us up before a major snow storm. We had a really nice time.
Guest favorite
A contemporary cabin features a unique slanted roof and large windows, allowing natural light to illuminate the interior. The wooden exterior is adorned with potted plants, and a spacious deck is visible, surrounded by lush greenery, providing a serene connection to nature.
Cabin in Hawley
4.97 out of 5 average rating, 264 reviews

the barn, by camp caitlin

AmandaRating, 5 stars4 weeks ago
We enjoyed our stay at Caitlin’s cabin! Communication was great. The place was spotless. I loved the many plants inside and the peaceful surrounding area filled with many deers visiting the yard. Soaking in the hot tub was so relaxing at night. And the fire pit outside was a really nice touch to our stay. I recommend this cabin and host! We didn’t get to enjoy the kayaks because of the weather, but it’s really nice that it was an option! Thank you!!

Family- and pet-friendly home rentals

Superhost
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
4.86 out of 5 average rating, 948 reviews

Dave's Milk Barn

JordanRating, 5 stars2 weeks ago
It’s a really sweet location on a working organic farm. The stairs to get to the loft are definitely for the agile, but otherwise it’s a nice little lay-out.
Top guest favorite
The exterior of the cabin is framed by lush greenery and colorful flower beds. A rustic wooden porch, accessed by a set of steps, features two prominent red doors. Surrounding foliage adds a natural ambiance to the inviting entrance.
Tiny home in Shandaken
4.87 out of 5 average rating, 190 reviews

Cute Cabin with Great Mountain Views

ChrisRating, 5 stars1 day ago
We had the best time staying at this cozy cottage, very comfortable with an awesome view! Kitchen had everything we would need. Great hospitality from Wayne and Renee! We can’t wait to come back again soon
Top guest favorite
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
4.98 out of 5 average rating, 511 reviews

Winston's Place - Woodland Cozy Catskills Cabin

IgorRating, 5 stars4 days ago
We had a really lovely stay at this cabin in Boiceville. It rained every day during our trip, but honestly, we didn’t mind—it made the space feel extra cozy. We spent our time relaxing indoors, reading, cooking, and just enjoying the slower pace. The cabin was clean, comfortable, and had everything we needed. It was tucked away enough to feel peaceful, but still a short drive to Esopus Creek and Phoenicia, which we enjoyed exploring when the rain let up. The host was helpful and easy to communicate with, and everything about the stay went smoothly. If you’re looking for a calm, quiet retreat in the Catskills—even on rainy days—this spot is a great pick.
Guest favorite
A bright living area features large windows that allow natural light to fill the space. A comfortable sofa is centered on a patterned area rug, complemented by a glass coffee table. Shelves hold various books and decorative items, while a wood-burning stove provides warmth.
Cabin in Big Indian
4.96 out of 5 average rating, 271 reviews

Retro Modern Paradise in the Catskills

AlecRating, 5 stars3 weeks ago
Would absolutely stay again! Really loved the way they've updated the space but kept the classic touches of the house. Huge well appointed kitchen with everything you could need. Peaceful outdoor space with lots of privacy. And overall a very spacious house that feels like you could have a big group without getting in each others way. Ryan & Lauren were super on it. Will definitely recommend to friends.
Guest favorite
The exterior view of a one-room schoolhouse is shown, featuring solar panels on the roof. A welcoming porch and large window enhance the facade, while colorful flowers bloom along the front garden. The surrounding greenery creates a natural, serene setting.
Home in Livingston Manor
4.9 out of 5 average rating, 134 reviews

Cozy renovated One Room Schoolhouse

BeverlyRating, 5 stars1 month ago
Jane’s Old Schoolhouse is awesome. Whimsical, relaxed, well equipped kitchen, loved all the little knooks to curl up with a book & cup of coffee or wine. Would love to enjoy the porches, however both visits offered us rain & cool weather. Great for doing puzzles & enjoying the wood stove.
Guest favorite
A Craftsman-style home is set on a spacious lawn surrounded by trees. The covered porch features seating arrangements and stacked firewood, while the vibrant greenery adds to the serene atmosphere. A pathway leads to the house from the yard, inviting relaxation.
Home in Lake Huntington
4.87 out of 5 average rating, 106 reviews

Beautiful Craftsman Home in Lake Huntington

MicheleRating, 5 stars4 weeks ago
Great place to stay after seeing a show at Bethel Woods. Easy to find and less than 15min drive to catch the show. Erik was easy to work with as well. We will def book his place again when we come back for another show!
Guest favorite
A spacious living area features large windows allowing ample natural light, surrounded by greenery. Comfortable seating arrangements include a blue sofa and armchairs with red accents. A patterned area rug anchors the space, complemented by a wooden coffee table and decorative wall elements.
Home in Livingston Manor
4.96 out of 5 average rating, 231 reviews

Wooded Livingston Manor Oasis With Stream & Deck

AllisonRating, 5 stars1 week ago
My husband, sons (newborn and toddler) and I had a wonderful stay at Karina's cabin. It was spacious and suitable for families with lots of activities and games. We enjoyed our time in Livingston Manor, including attending the Trout Parade. dinner. The location is close to Main Street for shopping and restaurants and the boys had a great time relaxing by the stream between exploring the area.
Guest favorite
A quaint cottage with a wooden exterior is nestled among trees and colorful foliage. Two Adirondack chairs sit on the grassy area in front, providing a serene spot to enjoy the view of nature and nearby mountains.
Cottage in Kerhonkson
4.88 out of 5 average rating, 552 reviews

Mod Scandinavian! Tiny Flower Farm

EliotRating, 5 stars2 weeks ago
Our stay was great. Super clean abode in a very tranquil setting—woke up to birds chirping! Host was very responsive to our several questions. All in all a good visit, and we would stay there again!

Family-friendly home rentals with a pool

Guest favorite
A private heated pool is set against a backdrop of lush trees, with water reflecting a clear blue sky. Relaxing lounge chairs surround the pool area, offering a serene view of the lake beyond, creating an inviting outdoor space.
Home in Bushkill
4.91 out of 5 average rating, 118 reviews

Sale: June 27-28, Pvt Heated Pool OPEN, Hot Tub

ShevaRating, 5 stars2 weeks ago
Such a beautiful spot on the lake!!! We had the most beautiful weekend, the kids loved he pool and the boats, nothing was missing! We would have stayed another week! Jennifer and Jose answered all our messages within a few minutes and were super accommodating. We will definitely be back!
Guest favorite
A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Top guest favorite
The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.
Home in Saugerties
4.94 out of 5 average rating, 131 reviews

Bluestone Escape - Where everyone is at home.

LoriRating, 5 stars1 month ago
Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!
Top guest favorite
An aerial view showcases a spacious home surrounded by lush greenery, featuring a 33-foot round swimming pool in the backyard. The inviting pool is surrounded by a deck, with lounge chairs positioned nearby, providing a serene outdoor setting.
Home in Tobyhanna
4.8 out of 5 average rating, 129 reviews

Cozy home for 10 ~ Private pool, BBQ, fire pit

EsteeRating, 5 stars4 months ago
We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.
Guest favorite
A spacious outdoor pool is surrounded by a stone patio, landscaped with shrubs and trees. Red umbrellas provide shade over lounge chairs that are arranged neatly along the pool's edge. The colorful building in the background complements the serene setting.
Condo in Vernon Township
4.95 out of 5 average rating, 191 reviews

Comfy Studio at Mountain Creek Resort

LaurieRating, 5 stars1 week ago
This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!
Guest favorite
The exterior of The Appalachian Lodge is displayed, showcasing a multi-story building with a combination of warm colors and architectural details. A heated outdoor pool and lounging area are visible in the foreground, surrounded by landscaped grounds and comfortable seating options.
Condo in Vernon Township
4.94 out of 5 average rating, 850 reviews

Appalachian Lodge Top Floor w/views

RebeccaRating, 5 stars4 days ago
Paul's place was just as described. My husband and I had difficulty figuring out the thermostat and he was quick to reply to our request for help. The pool and hot tub were great! Very comfortable bed.
Guest favorite
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars4 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Guest favorite
A scenic aerial view showcases an outdoor pool surrounded by greenery, with mountain vistas in the background. Lounge chairs line the poolside, inviting relaxation. The property features a blend of manicured gardens and natural landscaping, creating a peaceful environment.
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 months ago
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$16,737 GYD before taxes and fees

  • Total number of reviews

    360 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore