Family-friendly holiday 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 favourite
Home in Bearsville
4.92 out of 5 average rating, 230 reviews

A Cozy’s Woodstock Getaway Home

ClancyRating, 5 stars1 month 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 stars4 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!
Guest favourite
Home in Rhinebeck
4.91 out of 5 average rating, 232 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

ShannonRating, 5 stars3 weeks ago
Enrique's place was conveniently located near Rhinebeck, but alao far enough away that it was peaceful and quiet. Worth having a drink in the tavern at Beekman Arms and breakfast sandwiches at Rhinebeck Bagels. We especially enjoyed the hot tub. Enrique was a wonderful, informative host, and available if we needed (we didn't). Overall, we had a nice, relaxing weekend.
Superhost
Home in Olivebridge
4.92 out of 5 average rating, 457 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

VictoriaRating, 5 stars2 weeks ago
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!
Guest favourite
Chalet in Jewett
4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Gina-LouiseRating, 5 stars2 months ago
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!
Superhost
Home in Chichester
4.87 out of 5 average rating, 141 reviews

Make it your home away from home

HungRating, 5 stars2 months 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 favourite
Home in Roxbury
4.99 out of 5 average rating, 240 reviews

Charming Cottage on 12 Secluded Acres + Hot Tub

ThomasRating, 5 stars3 weeks ago
We stayed at the cottage this past weekend where it turned into a beautiful winter wonderland! The cottage is immaculate and very well decorated, making it feel like home away from home. It is tucked away in the mountains and couldn’t be more peaceful, truly a perfect place to relax! We would highly recommend Quinn’s place to family and friends for a Catskills weekend escape!
Guest favourite
Cabin in Woodstock
4.84 out of 5 average rating, 144 reviews

Contemporary Cabin With Fireplace

SlavoRating, 5 stars4 months ago
Amazing cabin , close to everything, clean ,

Family- and pet-friendly home rentals

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 stars4 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 Willow
4.86 out of 5 average rating, 250 reviews

Peace Cottage

SarahRating, 5 stars2 months 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.
Top Guest favourite
Home in Saugerties
4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

OrionRating, 5 stars3 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 stars1 month 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, 228 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars2 weeks ago
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!
Guest favourite
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Top Guest favourite
Farm stay in West Simsbury
4.96 out of 5 average rating, 482 reviews

Flamig Farm Staycation

CindyRating, 5 stars2 weeks ago
My husband and I had a wonderful 3-day stay with our 6 year old granddaughter. She enjoyed making herself at home in the lovely space. Nice deck and grill for eating in the evening. She especially loved all of the animals from the dogs and cats to the emus. She enjoyed learning their names, feeding them and watching l, interacting or tagging along with the owners and various caretakers. Everyone was so kind and welcoming. There is a great playground, various hiking and restaurant options, and a fantastic public library in Simsburg. Highly recommend!
Guest favourite
Holiday home in Hudson
4.9 out of 5 average rating, 122 reviews

2 blocks to Warren ST w/ a yard and parking

ArinRating, 5 stars2 weeks ago
We stayed here for two nights. It was clean with a lot of space for our family of three. It was an easy and quick walk to the main street in Hudson.

Family-friendly home rentals with a pool

Top Guest favourite
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 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 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 stars2 weeks 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 stars3 weeks 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
Apartment in Saugerties
4.97 out of 5 average rating, 111 reviews

Lovely Creekside w pool/sauna near Woodstock

MelissaRating, 5 stars8 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.
Guest favourite
Home in Woodstock
4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars7 months ago
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼
Guest favourite
Home in Cold Spring
4.95 out of 5 average rating, 167 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

ChristopherRating, 5 stars1 month ago
We had a peaceful and relaxing stay at Shawna’s beautiful Cold Spring country-style home. We were in town for a family gathering and accommodations, cleanliness and Shawn’s communication were five star. We absolutely recommend the house and Shawna as a host for you to stay with!

Quick stats about holiday rentals that are family-friendly in Sherman

  • Total rentals

    40 properties

  • Nightly prices starting at

    $200 AUD before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

Destinations to explore