
Family-friendly vacation rentals in New Fairfield
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Top-rated family-friendly rentals in New Fairfield
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Popular amenities for New Fairfield family-friendly rentals
Family-friendly home rentals with a hot tub

A Cozy’s Woodstock Getaway Home
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.

2 BR , Fireplace & Hot Tub @ heart of Woodstock
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!

Secluded Artist's Retreat with Hot tub
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!

Rhinebeck Home with an amazing outdoor space+H/tub
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.

Mountain-Top Catskills Getaway Cabin w/hot tub
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!

The Mountaintop Lakehouse that Time Forgot.
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!

Contemporary Cabin With Fireplace
Amazing cabin , close to everything, clean ,

Mountain View Retreat
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

Stunning Modern Barn minutes from Woodstock 21N195
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.

Peace Cottage
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.

Historic 1 BR Family Home Near Buttermilk Falls
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!

Mountaintop Skyloft
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.

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

Welcome to Malden Manor, in a prime location!
Lovely place in Saugerties, close to lots of great hiking and restaurants.

Wallkill Inn
This house was nice, steap stars. one hour away from all three locations JW branches.

Entire lake house to yourself. Great for groups
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

Shula | Farmhouse | Pool, Fire pit, Hot tub
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!

midcentury mod * POOL * walk out trail to mohonk
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.

Spacious Staycation near HITS & the Hudson
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!

Garden Level Suite with Beautiful Pool
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!

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

Modern Upstate Cabin, near Rhinebeck NY
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.

MODERN FARMHOUSE in the WOODS
We had a terrific stay. The house was exactly as advertised.

Stunning Views, Bucolic Bliss in 1790s Farmhouse
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
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- Rentals with a patio New Fairfield
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- Fairfield Beach
- Rye Beach
- Yale University
- Yankee Stadium
- Rye Playland Beach
- Inwood Hill Park
- Bronx Zoo
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Walnut Public Beach
- TPC River Highlands
- Rye Town Beach
- Seaside Beach
- Sunken Meadow State Park
- Bethpage State Park
- Woodmont Beach
- Taconic State Park
- Jennings Beach
- Thunder Ridge Ski Area
- Ringwood State Park
- Rockland Lake State Park
- Marvin Beach
- Walkway Over the Hudson State Historic Park
- Bushnell Park