Family-friendly vacation rentals in Sherman

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Sherman family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Bearsville
4.92 out of 5 average rating, 228 reviews

A Cozy’s Woodstock Getaway Home

AlexRating, 5 stars1 month ago
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.
Guest favorite
Home in Woodstock
4.83 out of 5 average rating, 109 reviews

2 BR , Fireplace & Hot Tub @ heart of Woodstock

RonRating, 5 stars4 months ago
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.
Guest favorite
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 favorite
Home in Rhinebeck
4.91 out of 5 average rating, 230 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

AudreyRating, 5 stars3 weeks 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, 452 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

KathleenRating, 5 stars3 weeks ago
Very secluded and cozy - the perfect spot to unwind. Can’t wait to go back!
Superhost
Home in Chichester
4.87 out of 5 average rating, 141 reviews

Make it your home away from home

HungRating, 5 stars1 month ago
I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!
Top guest favorite
Home in Saugerties
4.96 out of 5 average rating, 163 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

PaulRating, 5 stars3 months ago
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.
Guest favorite
Cabin in Woodstock
4.85 out of 5 average rating, 143 reviews

Contemporary Cabin With Fireplace

SlavoRating, 5 stars3 months ago
Amazing cabin , close to everything, clean ,

Family- and pet-friendly home rentals

Guest favorite
Home in Mount Tremper
4.9 out of 5 average rating, 222 reviews

Stunning Modern Barn minutes from Woodstock 21N195

KellyRating, 5 stars3 weeks ago
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.
Guest favorite
Cottage in Willow
4.86 out of 5 average rating, 250 reviews

Peace Cottage

SarahRating, 5 stars3 weeks 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.
Superhost
Cottage in Woodstock
4.85 out of 5 average rating, 143 reviews

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

JoshuaRating, 5 stars1 month ago
Great location, walking distance to the town center, and great good all around. the sauna is definitely the best part of the airbnb
Top guest favorite
Home in Saugerties
4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

OrionRating, 5 stars2 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 stars2 weeks 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, 226 reviews

Entire lake house to yourself. Great for groups

MeganRating, 5 stars3 weeks ago
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!
Guest favorite
Cabin in Woodstock
4.97 out of 5 average rating, 147 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

TammyRating, 5 stars4 months ago
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.
Top guest favorite
Farm stay in West Simsbury
4.96 out of 5 average rating, 478 reviews

Flamig Farm Staycation

DanaRating, 5 stars3 days ago
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

Top guest favorite
Chalet in Catskill
4.96 out of 5 average rating, 189 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

VeraRating, 5 stars1 month ago
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!
Guest favorite
Townhouse in Hunter
4.91 out of 5 average rating, 155 reviews

Peak Foliage - Stay at THE Ideal Hunter Home

RodRating, 5 stars4 months ago
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
Top guest favorite
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars5 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 favorite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars1 month 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 favorite
Cabin in Red Hook
4.96 out of 5 average rating, 345 reviews

Modern Upstate Cabin, near Rhinebeck NY

JohnnyRating, 5 stars2 weeks ago
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!”
Guest favorite
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars5 months ago
We had a terrific stay. The house was exactly as advertised.
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 184 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

AndreaRating, 5 stars2 months ago
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!
Guest favorite
Apartment in Saugerties
4.97 out of 5 average rating, 111 reviews

Lovely Creekside w pool/sauna near Woodstock

MelissaRating, 5 stars7 months ago
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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