
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

The 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!

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.

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
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!

Mountain-Top Catskills Getaway Cabin w/hot tub
Very secluded and cozy - the perfect spot to unwind. Can’t wait to go back!

The Mountaintop Lakehouse that Time Forgot.
Perfect Lakehouse Getaway for Our Anniversary Weekend! Our anniversary weekend at this lakehouse was nothing short of amazing! From the moment we arrived, we were blown away by the peaceful surroundings and stunning lake views. The house itself was spacious, beautifully decorated, and well-stocked with everything we needed for a comfortable stay. We brought our dog, Faith, along, and she absolutely loved exploring the outdoor space. It was great to have a pet-friendly rental that didn’t compromise on cleanliness or amenities. The hosts were thoughtful, providing clear instructions and quick responses to any questions we had. Spending the weekend with my wife and friends made the experience even more special. Whether we were relaxing by the water, cooking together in the well-equipped kitchen, or just enjoying the cozy ambiance, it was the perfect place to create lasting memories. If you’re looking for a serene, I highly this house. We’ll definitely be back!

1834 Farm House
Words simply cannot describe how magical this Airbnb experience was. a group of friends and I passed the hours marveling at the gorgeous art and curated knick-knacks - the home itself an endless source of fun. - like an interactive museum! Thats without even mentioning the property, the pond, the waterfall, the chickens, tire swings and HOT TUB! Truly a miraculous experience, would highly recommend and we will absolutely be returning.

Mountain View Retreat
The house was super easy to get in to and the second I walked in I was amazed at how nice it looked. Everything was very clean and I felt at home. Linda also leaves instructions to use all of the amenities!
Family- and pet-friendly home rentals

Stunning Modern Barn minutes from Woodstock 21N195
What an absolutely fantastic property! The home was perfect for our party of eight adults for a 50th birthday. Woodstock is the most adorable town with tons of fun things to do. You must get the stuffed bagels from moonrise. We couldn’t have expected a better experience with the house, the amenities, and The kitchen was very well appointed. I would absolutely come back here again and probably will.

The Mission House Sanctuary
The house was lovely and very clean and Piotr was an excellent host and even met us at check in to show us around. There are 4 bedrooms and each bedroom has its own bathroom which was very convenient for us. The kitchen was well stocked and It was very comfortable stay for my family of 7 adults and two babies and two dogs. One bedroom is on the main floor and two bedrooms are on the walkout lower level and one bedroom is on the upper floor. To get to the upper floor there is a steep winding staircase that wasn’t an issue for us, but I would not recommended it for small children or toddlers. The outdoor hot tub was a nice addition.

Historic 1 BR Family Home Near Buttermilk Falls
Traveled back to this area for several New Year’s celebrations. Extremely convenient to Buttermilk Falls Farms and nearby restaurants. Will stay here again in the future.

Hudson Valley Mountaintop Riverview
Beautiful home and nice getaway from the city! Highly recommend this property for anyone looking for a relaxing weekend, beautiful views and amazing home. Thank you for a wonderful stay! We look forward to coming back!

Whispering Pines: Secluded Retreat near town
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! :)

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's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

Litchfield County Getaway
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

Escape to a Restored New England Antique Milk Barn
When my plumbing went rogue and turned my floor into a squishy disaster zone, I needed a place to crash that wasn’t half underwater. Enter Sally’s place—a true oasis in my time of crisis. First off, this place is so nice that I briefly wondered if my house was even worth saving. It’s cozy, beautifully decorated, and so clean. The bedroom and bathroom are upstairs, making me feel like I was living the high life—literally. The bed? Like sleeping on a cloud. The view? So peaceful I considered writing poetry. Bottom line: If you need a place to stay, stop scrolling. Just book it. But be warned—you may never want to leave.

Private Hudson Valley Country Retreat
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

midcentury mod * POOL * walk out trail to mohonk
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!

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!

Private apartment in rural home
I had a lovely stay at Sherrill and Clark's! I stayed for a month while working a job in the area, so I wasn't around much, but the space was a very cozy and homey place to come back to at the end of each day. Sherrill and Clark were very kind and welcoming. The bed was big and comfy! If you live in a city and need some time away New Paltz is adorable. Being from Chicago, it was a great change of pace.

Modern Upstate Cabin, near Rhinebeck NY
We had an amazing stay at Tina’s Airbnb! The house was beautiful, peaceful, and perfect for a relaxing getaway. Tina was incredibly accommodating, allowing us to check in early and stay longer. We loved the large windows, high ceilings, and especially the glass door that opened to fresh air. My wife particularly enjoyed the bathtub. We had a wonderful, restful time and will definitely be visiting again!”

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

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Our 2nd stay at Elizabeth’s house and it was as nice as our last visit. Our kids love exploring the home and property which has a wonderful view. The kitchen is well appointed for cooking. We especially enjoyed the stone fireplace to relax after skiing. Would highly recommend!
Quick stats about vacation rentals that are family-friendly in New Fairfield
Total rentals
80 properties
Nightly prices starting at
$113 CAD before taxes and fees
Total number of reviews
2.4K 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
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- Yale University
- Yankee Stadium
- Inwood Hill Park
- Catamount Mountain Ski Resort
- Bronx Zoo
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Taconic State Park
- Bethpage State Park
- Woodmont Beach
- Marvin Beach
- South Pine Creek Beach
- Oakland Beach
- Rye Town Beach
- Lloyd Beach
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Sasco Hill Beach
- Steer's Beach
- Mohawk Mountain Ski Area
- Opus 40
- Thaddeus Hait Farm
- Kent Falls State Park