Family-friendly vacation rentals in New Fairfield

Find and book unique family-friendly homes on Airbnb

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Popular amenities for New Fairfield family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Bearsville
4.92 out of 5 average rating, 230 reviews

A Cozy’s Woodstock Getaway Home

ClancyRating, 5 stars1 month 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
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 favourite
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 favourite
Home in Rhinebeck
4.91 out of 5 average rating, 233 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

BellaRating, 5 stars3 weeks ago
The beds are comfortable. The kitchen is well stocked. The deck is lovely. The hot tub is awesome. We had a great stay! Some good restaurants only about 10 minutes away.
Superhost
Home in Olivebridge
4.92 out of 5 average rating, 457 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

VictoriaRating, 5 stars2 weeks ago
This place was perfect! Peaceful with beautiful surroundings, and the hot tub was the cherry on top! Super clean and felt right at home. We loved it and highly recommend staying here!
Top guest favourite
Cottage in Highland Lakes
4.97 out of 5 average rating, 322 reviews

The Mountaintop Lakehouse that Time Forgot.

NathanRating, 5 stars1 week ago
A hidden gem! This spot has a ton of character and the hosts are awesome! The lake and surrounding area is beautiful as well, with plenty to do for the outdoorsy type and cute shops and great restaurants within minutes. would highly recommend and hope to find time for a return trip!
Guest favourite
Cabin in Woodstock
4.84 out of 5 average rating, 144 reviews

Contemporary Cabin With Fireplace

SlavoRating, 5 stars4 months ago
Amazing cabin , close to everything, clean ,
Guest favourite
Chalet in Cold Spring
4.9 out of 5 average rating, 445 reviews

Mountain View Retreat

AndreaRating, 5 stars1 week ago
My family and I wanted to get away from the city for a few days. This Airbnb was the perfect place for it. We were able to enjoy the peaceful home and the beautiful view of nature from her home. Linda’s home felt like our home away from home, amenities were fully stocked. Everything that we needed during our stay, we were able to find. She left very helpful notes and descriptions of how to check-in, check-out and instructions for the home. 10/10 recommend.

Family- and pet-friendly home rentals

Guest favourite
Home in Mount Tremper
4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars1 month 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 favourite
Cottage in Willow
4.86 out of 5 average rating, 250 reviews

Peace Cottage

SarahRating, 5 stars2 months 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 favourite
Home in Milton
4.75 out of 5 average rating, 178 reviews

Historic 1 BR Family Home Near Buttermilk Falls

DianeRating, 5 stars3 weeks 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 favourite
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
Cottage in Woodstock
4.84 out of 5 average rating, 146 reviews

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

AdaRating, 5 stars1 month 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 favourite
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
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
Home in Ulster Park
4.88 out of 5 average rating, 228 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars2 weeks 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
Home in Woodstock
4.88 out of 5 average rating, 162 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!
Top guest favourite
Home in New Paltz
4.98 out of 5 average rating, 484 reviews

midcentury mod * POOL * walk out trail to mohonk

GosiaRating, 5 stars2 weeks 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 favourite
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!
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Saugerties
4.94 out of 5 average rating, 140 reviews

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

BrittanyRating, 5 stars3 weeks ago
Stayed with 5 children and our dog… this home was super kid and family friendly. The yard was our favorite- fenced in, well taken care of, and the trampoline was a hit. The deck was clean and had comfortable places for lounging. Inside the kitchen had all the amenities needed to cook for ourselves, the space was super clean, and the beds were very comfortable. We would love to visit again!
Top guest favourite
Cabin in Red Hook
4.96 out of 5 average rating, 349 reviews

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars2 weeks 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 favourite
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 favourite
Home in Litchfield
4.93 out of 5 average rating, 185 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

TessaRating, 5 stars3 weeks ago
This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!

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

  • Total rentals

    90 properties

  • Nightly prices starting at

    $181 CAD before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 properties include access to wifi

Destinations to explore