
Family-friendly holiday rentals in Sherman
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Top-rated family-friendly rentals in Sherman
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Family-friendly home rentals with a hot tub

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
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.

Mountain-Top Catskills Getaway Cabin w/hot tub
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!

Private Catskills Home w. Hot Tub, near Ski Mnt
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

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!

Charming Cottage on 12 Secluded Acres + Hot Tub
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!

Contemporary Cabin With Fireplace
Amazing cabin , close to everything, clean ,
Family- and pet-friendly home rentals

Stunning Modern Barn minutes from Woodstock 21N195
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.

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.

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 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!

Pet Friendly Cabin Doh-Ray up at 1450 ft
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Flamig Farm Staycation
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!

2 blocks to Warren ST w/ a yard and parking
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

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
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.

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

Stunning Views, Bucolic Bliss in 1790s Farmhouse
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!

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.

Woodstock Romantic Mountain Studio w/ Pool
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 👍🏼

Cozy, Modern Retreat in the Woods of Cold Spring
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
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- Fairfield Beach
- Rye Beach
- Yale University
- Rye Playland Beach
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Walnut Public Beach
- TPC River Highlands
- Rye Town Beach
- Seaside Beach
- Sunken Meadow State Park
- Woodmont Beach
- Taconic State Park
- Jennings Beach
- Thunder Ridge Ski Area
- Ringwood State Park
- Rockland Lake State Park
- Marvin Beach
- Walkway Over the Hudson State Historic Park
- Bushnell Park
- Brotherhood, America's Oldest Winery
- Oakland Beach
- Stehli Beach
- West Beach