Family-friendly vacation rentals in Sherman

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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, 223 reviews

A Cozy’s Woodstock Getaway Home

NicholasRating, 5 stars1 week ago
Boris and Rungcheewan’s place was very peaceful and nice. The cabin is private, and has everything you need. They were both proactive in plowing the driveway multiple times throughout our stay to make sure we were safe and could easily access everything. I would highly recommend both this place and the hosts.
Guest favorite

Home in Woodstock

4.83 out of 5 average rating, 108 reviews

2 BR , Fireplace & Hot Tub @ heart of Woodstock

RonRating, 5 stars2 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, 132 reviews

Secluded Artist's Retreat with Hot tub

DavidRating, 5 stars1 month 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 favorite

Home in Rhinebeck

4.91 out of 5 average rating, 227 reviews

Rhinebeck Modern Home with amazing outdoor space

MichelleRating, 5 stars4 weeks ago
House was spotlessly and thoughtfully decorated. The bed was comfortable and hot tub was absolutely phenomenal. Skylights let in beautiful natural light for reading and relaxing. Michael and Enrique were proactive about reaching out beforehand with the house information and we really, really enjoyed our stay. We're not used to baseboard heating so some of the noise from the heating surprised us, but that's to be expected with any place that's not your home. Would gladly stay here again.
Superhost

Home in Olivebridge

4.92 out of 5 average rating, 447 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

JamesRating, 5 stars1 week ago
Big thanks to Ethan and Wray for the extended weekend cozy stay! My wife and I went with our three kids and had a great time. Close to many hikes, this location was perfect. Near woodstock (35-40 mins) and also catskills. The place is very cozy, clean and stylish. We stayed during a snow storm and at no point were we cold (which was a concern). The temperature is always comfortable. Also, hot water was actually hot and not lukewarm like some places in these neck of the woods. It was private, no one bothered us and they were helpful when we reached out. We stayed during a snow storm and woke up to 8 inches of snow and were able to safely head out. Note: if coming in winter, dont chance it and come with a 4 wheel drive vehicle. Hot tub worked amazing. We didn’t have to press any buttons or do any prep it was just remove the cover and jump on it. Yard is huge and kids can run around in the woods. No complaints— great stay.
Superhost

Home in Chichester

4.88 out of 5 average rating, 138 reviews

Make it your home away from home

YuRating, 5 stars4 weeks ago
Tracy’s home was amazing. We were 2 adults and 5 teens, the space was perfect for a family.
Guest favorite

Home in Saugerties

4.96 out of 5 average rating, 162 reviews

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

PaulRating, 5 stars1 month 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.
Superhost

Home in woodstock

4.86 out of 5 average rating, 506 reviews

CABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN

HeatherRating, 5 stars2 months ago
Had an enjoyable stay at Ralph’s Woodstock location. Ralph was accommodating regarding the hot tub, as it was not working during our stay- We really appreciate it! The area itself was secluded and peaceful. The town of Woodstock was super cute. A great place to relax and unwind!

Family- and pet-friendly home rentals

Guest favorite

Home in Mount Tremper

4.9 out of 5 average rating, 218 reviews

Stunning Modern Barn minutes from Woodstock 21N195

AmélieRating, 5 stars1 week ago
Lovely house, spacious and really pleasant for our group of friends with kids! The jacuzzi was a big plus! We really enjoyed our stay!
Guest favorite

Cottage in Willow

4.85 out of 5 average rating, 247 reviews

Peace Cottage

TimRating, 5 stars1 month ago
In Woodstock NY you want a feeling of charm and fun with a bit of old style funk! Colorful and cheerful. Heat was great for cold nights. The yard and stream were magical. I was there with my active dog and never had to worry about him. He could hang out and be safe. I can only imagine the spring and summer here as I lived in Woodstock many years ago. The town is vibrant and has everything you need and more. I would highly recommend this Airbnb -
Guest favorite

Home in Saugerties

4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

BrandonRating, 5 stars1 month ago
Bonnie’s home was perfect. Our group of 7 including 2 young children fit perfectly in the home. It’s to downtown Saugerties, and a short drive from all the Hudson Valley has to offer.
Superhost

Home in Wallkill

4.87 out of 5 average rating, 167 reviews

Wallkill Inn

LauraRating, 5 stars4 months ago
I am so glad that I found Yvonne's place. It was perfect for my group. Clean, tons of beds, laundry facilities, and a great kitchen that enabled 9 or so of us to cook dinner for a group of 20. We were so thrilled to learn there was a propane grill with propane in it, ready to go. The beds were comfortable. The showers provided plenty of hot water. The living room was comfy and cozy with nice couches that were comfortable enough to sleep on. I would stay here again and again if the opportunity arises.
Superhost

Home in Ulster Park

4.88 out of 5 average rating, 221 reviews

Entire lake house to yourself. Great for groups

AnnamariaRating, 5 stars2 months ago
Scott hosted my friends and I in a beautiful home on the water. We enjoyed water sport activities, even in November! We were 10 minutes away from New Paltz and 10 minutes away from hiking spots! The house was east to locate, check-in to, and Scott communicated very effectively. We were even granted late check-out! The house was very charming, well-stocked, and clean. One of my favorite touches was the “pet essentials” corner. Scott provided our pup with a bed, food bowls, and a leash - very thoughtful! His rules are clearly explained and easy to follow. I would definitely recommend a stay at Scott’s and would love to return next time I’m looking to stay in the area.
Guest favorite

Cabin in Woodstock

4.97 out of 5 average rating, 146 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

SusanRating, 5 stars2 months ago
The cabin was cozy, well equipped & welcoming. Can’t say that I’ve ever slept on a more comfortable bed! The kitchen was well stocked with modern appliances. The property was certainly private, expansive & peaceful…maybe a bit too quiet for a Bklyn girl! A but tricky to reach and phone & internet service disappear as soon as you walk out of the house. The hosts were exceptionally responsive & helpful.
Guest favorite

Farm stay in West Simsbury

4.96 out of 5 average rating, 471 reviews

Flamig Farm Staycation

DianeRating, 5 stars1 week ago
This is a quintessential farm-stay in a spacious apartment that is more like a home, with a farm table that seats 6 easily, the most comfortable beds, top quality linens, blankets and towels, an inviting living room with a pellet stove and all of it decorated beautifully with authentic and interesting farm-life paintings, pottery and more. It is a great place for families with young children but also just right for a couple looking for some R&R away from the bustle of daily living.
Guest favorite

Cabin in Saugerties

4.96 out of 5 average rating, 184 reviews

Rustic & Cozy Cabin Saugerties- near Hunter Mtn

AnnRating, 5 stars1 week ago
We had such a wonderful stay! The kitchen was incredibly well-stocked with pots, pans, and all the cooking equipment we needed—it made preparing meals so easy and enjoyable. The snowy weekend brought stunning scenery, and we loved just sitting by the windows, soaking in the beautiful views. The fireplace was a huge highlight! There was plenty of firewood and clear instructions to get it going, making for such cozy evenings. William was fantastic—super helpful and quick to respond to any questions we had, which made everything smooth and stress-free. This stay was everything we hoped for and more. Highly recommend! 🌟

Family-friendly home rentals with a pool

Guest favorite

Chalet in Catskill

4.96 out of 5 average rating, 187 reviews

Daydream Mountain Art-Chateau '73 | I ❤️ Catskill

AnthonyRating, 5 stars1 month ago
Olia was a fantastic host and was super diligent in making sure we had everything we needed. The house was beautiful and spacious and my family loved it. There were plenty of activities and things to do around the house and we all had such a fun time. Would definitely consider coming back in the future!
Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 475 reviews

midcentury mod *fireplace *walk out trail 2 mohonk

AmyRating, 5 stars2 weeks ago
I fell in love with Susan's place the moment I arrived! My guest and I felt welcome, safe, and cozy. We appreciated the spotless rooms, peaceful surroundings, and perfectly appointed amenities in each part of the home. We loved sitting by the fire watching the happy birds and squirrels in the yard. What a treat to walk down to the trail for sunset, right from the backdoor! Susan was kind, friendly, and helpful; check in/check out was a breeze. We had ample space to work and relax. What a dream. We will be back asap!
Guest favorite

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

CarolRating, 5 stars4 months ago
This was our third stay at Marybeth's, everything was great, as usual. The unit is spacious, clean, and very conveniently located.
Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 342 reviews

Modern Upstate Cabin, near Rhinebeck NY

PatrickRating, 5 stars4 weeks ago
A great get-away. Super comfortable, just as advertised, and with an incredibly stocked kitchen. Our dog had a blast romping in the yard, and my wife and I are already talking about going back in the summer. We loved it.
Guest favorite

Home in Saugerties

4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars3 months ago
We had a terrific stay. The house was exactly as advertised.
Guest favorite

Cottage in Woodstock

4.81 out of 5 average rating, 113 reviews

Woodstock Mountain View Cottage/pool book summer

AllisonRating, 5 stars2 months ago
Sunset Cottage was the absolute perfect place for us to spend a long weekend. The house is beautifully designed with modern touches like big windows with stunning mountain views. We loved the open lay out with the cozy living room and comfy beds in each bedroom that made it easy to relax after an upstate day. The cottage location is ideal with it actually being located in Woodstock vs many other airbnb’s that day they are but aren’t. We were just a 3 mins drive to Woodstock town where we had such good meals at Red Onion and Silvia, but felt far enough away to be immersed in nature. Each morning, we were greeted by a family of deer grazing in the yard! The house itself was incredibly clean and well-decorated, adding to the overall comfort and charm. The hosts were super friendly and gave us great tips on local hikes and restaurants. We're already dreaming of our next visit for a ski weekend or summer to use the pool!
Guest favorite

Farm stay in Rhinebeck

4.95 out of 5 average rating, 186 reviews

Majestic Oasis Rhinebeck - Hot Tub, Sauna, & Pool

MariaRating, 5 stars1 week ago
This property was perfect for a weekend get away for our group of 11. The setting is beautiful and provided opportunities for us to get outside and go sledding, do short walks, play ping pong and jump on the trampoline. The house was spacious enough for our group. The centerpiece is the kitchen which served as our hang out place as well as for eating and cooking. Rhinebeck is a cute village that is close by for shopping and eating out. We also enjoyed going to some local parks for more extensive walks. I messaged several times with Alina who was very helpful in answering questions about the house. We got snow our last night and she made sure that the driveway and walk ways were clear in the morning and allowed us a later check out because of the storm. All in all a great house!
Guest favorite

Home in Litchfield

4.93 out of 5 average rating, 182 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

CarlyRating, 5 stars4 weeks ago
We had a great stay over New Year’s! The house was spacious for 6 people and a dog with plenty of room to gather. The kitchen was very well equipped, and the land surrounding the house was beautiful. We enjoyed going into Litchfield for lunch - under 10 minutes away.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 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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