Family-friendly vacation rentals in New Windsor

Find and book unique family-friendly homes on Airbnb

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Popular amenities for New Windsor 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 stars4 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 well-maintained lawn stretches in front of the house, flanked by trees providing natural shade. A shelter with tables and chairs is positioned on the grassy area, creating a space for outdoor gatherings. Solar panels are visible on the roof of the house.
Home in Smallwood
4.79 out of 5 average rating, 162 reviews

Cozy Catskill Lake Community Home

PeterRating, 5 stars26 months ago
We had a lovely and relaxing weekend at John’s place. Thanks for the great local tips.
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!
Guest favorite
Home in Rhinebeck
4.91 out of 5 average rating, 231 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

ShannonRating, 5 stars2 weeks ago
Enrique's place was conveniently located near Rhinebeck, but alao far enough away that it was peaceful and quiet. Worth having a drink in the tavern at Beekman Arms and breakfast sandwiches at Rhinebeck Bagels. We especially enjoyed the hot tub. Enrique was a wonderful, informative host, and available if we needed (we didn't). Overall, we had a nice, relaxing weekend.
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 stars3 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 stars1 month 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
A spacious living area features a black sectional sofa adorned with colorful decorative pillows. A wooden coffee table sits in front, complemented by a comfortable armchair. The kitchen area is visible in the background with wooden cabinetry and modern appliances, while natural light enters through large windows.
Cabin in Woodstock
4.85 out of 5 average rating, 143 reviews

Contemporary Cabin With Fireplace

SlavoRating, 5 stars4 months ago
Amazing cabin , close to everything, clean ,

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 stars3 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!
Guest favorite
A serene pond is surrounded by lush greenery, reflecting the trees and sky. A blue pedal boat rests quietly at the dock, inviting exploration. The wooden dock leads into the calm waters, framed by tall grasses and vibrant plants.
Home in Millerton
4.92 out of 5 average rating, 399 reviews

Mountaintop Skyloft

GeorgeRating, 5 stars4 months ago
The loft was lovely: fireplace, large balcony, view down the mountain, TV with airplay support, kitchen, etc. the surrounding was quiet and peaceful. The host was responsive and very friendly. Would recommend to others.
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 stars3 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 stars1 week 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!

Family-friendly home rentals with a pool

Superhost
A spacious living area features a large sectional sofa and a fluffy area rug. Natural light floods the room, highlighting the hardwood floors. An open kitchen with modern appliances is visible in the background, while a dining area is located near the staircase.
Home in Woodstock
4.88 out of 5 average rating, 161 reviews

Shula | Farmhouse | Pool, Fire pit, Hot tub

LinnaRating, 5 stars2 months ago
Nice and clean house with a hot tub that is well maintained! Getting into the driveway was a bit scary due to the weather and plumbing is a bit finicky but we had a great stay overall and the owner was very prompt with responses!
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, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars5 months ago
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back
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, 484 reviews

midcentury mod * POOL * walk out trail to mohonk

GosiaRating, 5 stars6 days ago
This was our second stay at Susan's home. This is my favorite airbnb. I will always return to Susan's home if we need a getaway. I absolutely love her home. It is so close to nature. The windows look at nature. I could talk and talk about our experience so lets Susan give million stars. I love your home. Thank you, we will stay again.
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.
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 stars1 week 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.
Guest favorite
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

MelissaRating, 5 stars8 months ago
We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.

Quick stats about vacation rentals that are family-friendly in New Windsor

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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