Family-friendly holiday rentals in New Fairfield

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 New Fairfield family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
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 favourite
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.
Guest favourite
Home in Bearsville
4.92 out of 5 average rating, 134 reviews

Secluded Artist's Retreat with Hot tub

DavidRating, 5 stars3 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 favourite
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
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!
Top Guest favourite
Cottage in Highland Lakes
4.97 out of 5 average rating, 320 reviews

The Mountaintop Lakehouse that Time Forgot.

MaxRating, 5 stars1 week ago
Evalina and John were the best hosts we’ve ever had! There was a big winter storm during our trip and the power in the area went out briefly and John was over at our place turning on the generator right away. Highly recommend staying here
Guest favourite
Home in Cold Spring
4.91 out of 5 average rating, 256 reviews

1834 Farm House

FrankieRating, 5 stars1 month ago
We enjoyed a beautiful early spring stay on the farm with a group of 7 ladies, gathering for a chill bachelorette weekend in Cold Springs. The farmhouse was super cozy; great for cooking, crafting, games, tea time, outdoor wine picnics, star gazing at night in the hot tub and making friends with the chickens! A great retreat spot for groups with all the amenities!
Guest favourite
Home in Englewood
4.93 out of 5 average rating, 153 reviews

Englewood NJ Country Carriage House (15 min NYC)

VirginiaRating, 5 stars5 days 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

Family- and pet-friendly home rentals

Superhost
Home in Huntington
4.85 out of 5 average rating, 291 reviews

Nautical Farm House on Working Farm with Animals

HeatherRating, 5 stars1 month ago
The Farm House was adorable! The beds were very comfortable and it was very clean! Great history of the home and farm too! Rescued and restored and saved the land from condos! ❤️
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 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 favourite
Cottage in Woodstock
4.84 out of 5 average rating, 249 reviews

Woodstock Dog friendly Cottage in Town; large yard

PaulineRating, 5 stars1 month ago
Anne’s house was just right for my daughter and I with our two pups. Right around the corner from Tinker street was a great location. Nothing bad to say at all about home and stay.
Guest favourite
Home in Milton
4.75 out of 5 average rating, 178 reviews

Historic 1 BR Family Home Near Buttermilk Falls

DianeRating, 5 stars5 days 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 Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars2 weeks ago
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!
Top Guest favourite
Home in Woodstock
4.99 out of 5 average rating, 141 reviews

Whispering Pines: Secluded Retreat near town

VanessaRating, 5 stars3 months ago
Jason's home was lovely and accurately described & appointed - my friends and I spent a wonderful weekend with our pups and were even blessed by some snow! The fireplaces (yes - two!) were a great add-on and we were super excited to relax and enjoy all the home has to offer. Thanks so much again Jason! :)
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.
Guest favourite
Home in Warren
4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

DemianRating, 5 stars4 months ago
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend

Family-friendly home rentals with a pool

Top Guest favourite
Barn in Bethel
4.98 out of 5 average rating, 233 reviews

Escape to a Restored New England Antique Milk Barn

StaceyRating, 5 stars1 week ago
We had an amazing stay at Sally’s place in Bethel! My fiancé and I visited CT for the first time to celebrate my birthday and go to a convention nearby. This cottage was perfect for the two of us. The host was very responsive and accommodating as well! The cottage was in pristine condition, the house manual was very easy to follow, the recommendations were great, the scenery was out of a movie, and my favorite part was the hot tub in our restroom which was perfect after a long day! We had a great time and would love to come back again! Thanks for your hospitality Sally! ☺️
Guest favourite
Home in Stormville
4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars4 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 favourite
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 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!
Top Guest favourite
Cabin in Red Hook
4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars3 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 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 stars1 week 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!
Guest favourite
Guest suite in Guilford
4.96 out of 5 average rating, 157 reviews

Bright, Cozy Apartment in Guilford

KarenRating, 5 stars6 months ago
The home was absolutely gorgeous and peaceful. It's exactly as described but even more spacious than I expected. They put a lot into making guests feel welcome, including prompt communication, a quick walk through to explain where things are, numerous suggestions for the surrounding area, and even a tray of welcome cookies! I came for a 50k trail race, so the hot tub was a perfect added bonus. I HIGHLY suggest booking this property, and I'll definitely be back to spend some time at the beach.

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

  • Total rentals

    90 properties

  • Nightly prices starting at

    $204 AUD 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

  • Wi-Fi availability

    80 properties include access to Wi-Fi

Destinations to explore