
Family-friendly vacation rentals in Sherman
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Top-rated family-friendly rentals in Sherman
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Sherman family-friendly rentals
Family-friendly home rentals with a hot tub

A Cozy’s Woodstock Getaway Home
You feel secluded and private - everything you need to stay in - but also minutes from Woodstock and great restaurants. Beautiful views! Very romantic vibes, especially in the winter. The host was super helpful with communication about the weather. We got lots of snow and ice while there, and they made sure the steep driveway was well plowed and sanded for our departure.

2 BR , Fireplace & Hot Tub @ heart of Woodstock
What a peaceful wonderful time we had in this cherry red cabin. Thank you for warm healing waters, sunny blue skies with mountain views, cozy sleeps and wonderful times cooking and gathering around the cozy cabin. We unplugged, biked the reservoir, ate lots of yummy veggie food, danced at the Bearsville Theater, and breathed in the magical mountain air. Thanks Woodstock and much gratitude to our host Mirav for creating a wonderful retreat. Blessings.

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!

Make it your home away from home
I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!

Lux 1800's renovated farmhouse w/hot tub+pool
Loved the house. Kitchen is great. Awesome living room with very comfortable couch and fireplace. Bedrooms perfect. Hot tub was perfect. Original Nintendo system upstairs was fun. Went skiing at Hunter which is 20-25 min away. Woodstock 15 min away. Really a great place. Jaime was responsive, friendly and helpful.

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

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.

Rock City Writer's Studio: bucolic•sauna•walkable!
Great location, walking distance to the town center, and great good all around. the sauna is definitely the best part of the airbnb

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'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!

Pet Friendly Cabin Doh-Ray up at 1450 ft
I loved staying in this home and hope to rent it again. It is just a few minutes from town and nestled in the woods. The place is beautifully decorated and has everything you need.
Flamig Farm Staycation
My family of 4 had a wonderful getaway to Flamig Farm. In spite of the chilly and damp weather, we were all able to explore the farm, engage with the animals, participate in egg gathering and various other farm chores, and then relax and unwind by the pellet stove. What a wonderful and relaxing getaway with cozy accommodations, a very responsive and kind host, and wonderful people who worked at the farm. Having farm-fresh eggs for breakfast was delicious, and we also utilized the pancake mix that was provided one morning. We will definitely be back...thanks for a terrific escape back to nature!!
Family-friendly home rentals with a pool

Daydream Mountain Art-Chateau | Hot Tub & Pool
We, 2 families absolutely loved our stay. This is very unique house: lots of artsy stuff and interesting pieces around the house. We enjoyed exploring it. A lot of original pieces preserved from the 70th, that gives house the personality. The views are breathtaking- you can just sit next to the big windows and enjoy. Outside whirlpool also has view on the mountains. Skiing is 20 just min away. Olia is wonderful and generous host!

Peak Foliage - Stay at THE Ideal Hunter Home
Every thing very good thank you we’re thinking about to go back there from Jan 29 to fev second because we love the place

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!

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!

Lovely Creekside w pool/sauna near Woodstock
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 Sherman
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
1.4K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Yale University
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Taconic 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
- Beartown State Forest
- Thaddeus Hait Farm
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Sunken Meadow State Park
- Ringwood State Park