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, 221 reviews

A Cozy’s Woodstock Getaway Home

RichardRating, 5 stars2 days ago
Excellent home , very well decorated and comfortable , very much felt like a home we could live in , the interior was really laid out e trembly well with a great kitchen , super comfortable master sweet with a attached master bath, all very very clean and perfect for our stay.
Guest favorite

Home in Woodstock

4.83 out of 5 average rating, 108 reviews

2 BR , Fireplace & Hot Tub @ heart of Woodstock

RonRating, 5 stars1 month 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, 131 reviews

Secluded Artist's Retreat with Hot tub

JessicaRating, 5 stars1 month ago
This is our second time visiting the cabin. We absolutely love it! It is so scenic with beautiful patios to enjoy. Very spacious with fantastic amenities. They thought of everything! We didn’t want to leave
Guest favorite

Home in Rhinebeck

4.91 out of 5 average rating, 226 reviews

Rhinebeck Modern Home with amazing outdoor space

RyanRating, 5 stars1 month ago
Really enjoyed our two-night stay at Michael and Enrique’s place! They provided lots of clear instructions ahead of time and the place was quite easy to find. Their home is very well laid-out and cozy, and our dogs loved it too. Enrique is very communicative throughout. We will be back!
Superhost

Home in Olivebridge

4.92 out of 5 average rating, 445 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

AshleyRating, 5 stars1 month ago
This was the best airbnb I've ever stayed at! You can tell Ethan and Wray visit often and take really good care of the place. It is well stocked and loved and most importantly (to me) extremely comfortable. The beds are so cozy and the linens are not only adorable but so comfortable! The house has the best windows, from one of the beds you can even see the stars at night. It was just the best, I hope to come back soon!
Superhost

Home in Chichester

4.88 out of 5 average rating, 136 reviews

Make it your home away from home

CindyRating, 5 stars2 months ago
We had an amazing time at this beautiful, well-equipped house. It had everything we needed as a family, even for the little ones. The house was clean and cozy, and the hot tub was a fantastic bonus. Our host was responsive and provided clear, detailed instructions. Loved how close the house was to restaurants!
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 stars4 days 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 stars1 month 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, 216 reviews

Stunning Modern Barn minutes from Woodstock 21N195

KatherineRating, 5 stars1 month ago
The house was clean and beautiful. We had some questions because our stay was over thanksgiving. They were responsive and helpful. The house is beautiful, warm and friendly. I highly recommend them and this house!!
Guest favorite

Home in Saugerties

4.97 out of 5 average rating, 125 reviews

Welcome to Malden Manor, in a prime location!

ElizabethRating, 5 stars1 week ago
Bonnie is an amazing host, so helpful and communicative! I had a ton of questions prior to booking, because I have a family member with physical health & mobility issues, and she went above and beyond in answering questions. The home is lovely, and I would definitely stay there again!
Superhost

Home in Wallkill

4.88 out of 5 average rating, 166 reviews

Wallkill Inn

LauraRating, 5 stars3 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 stars1 month 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 stars1 month 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, 465 reviews

Flamig Farm Staycation

KatherineRating, 5 stars1 day ago
We had a great time at Flamig Farm, we stayed for new years with a baby and teen, 2 dogs. It was off season so we had the whole farm to ourselves and visited the animals each morning. Loved that. We brought all of the cooking items we thought we’d need; Dutch oven. The kitchen was stocked with some essentials, minus a wine opener! We figured it out. We visited and hiked at Roaring Brook Nature Center and went to Little Red Barn for lunch. Onion Mt park is a 2 min drive. Julie’s place was unique and homey. I appreciated all the toys and pack and play. I’d love to go back when my little is older to really engage the farm.
Guest favorite

Cabin in Saugerties

4.96 out of 5 average rating, 181 reviews

Rustic & Cozy Cabin Saugerties- near Hunter Mtn

AmandaRating, 5 stars1 month ago
We always have a great time at this cozy cabin. It’s secluded, peaceful, and a great place to bring our city dog to enjoy nature.
Guest favorite

Home in West Kill

4.94 out of 5 average rating, 119 reviews

Catskill Mountain Cabin Waterfall Retreat

AlyssaRating, 5 stars2 months ago
Had a fantastic fall family trip here. This was our second time staying at Gavin and Alison’s and it was even better than the first! Beautiful fall foliage, very clean home, excellent communication with the hosts. We enjoyed so many indoor and outdoor fires, played games, and the dogs loved running in the backyard. The creek is a must see! Thanks for everything, can’t wait to return!

Family-friendly home rentals with a pool

Guest favorite

Chalet in Catskill

4.96 out of 5 average rating, 186 reviews

Daydream Mountain Art-Chateau '73 | I ❤️ Catskill

AnthonyRating, 5 stars4 days 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, 472 reviews

midcentury mod cozy fireplace hike trail 2 mohonk

AlisonRating, 5 stars2 weeks ago
This was our second time at Susan's home. The first time was with our children and this time was a solo trip for just my husband and I. It has become one of my favorite places to stay and vacations to look forward to. Her home is immaculate, beautiful and most of all a real home. The location is perfection with huge windows that allow you to stay inside but feel like you are outside in the gorgeous nature surrounding the home. We will be back again asap.
Guest favorite

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

CarolRating, 5 stars3 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

Home in Saugerties

4.94 out of 5 average rating, 139 reviews

Saugerties 5BR Close to Village Diamond Mills HITS

cherylRating, 5 stars1 month ago
A beautiful house in a pretty central location. We are originally from the area and this house made us feel right at home. It’s clean, inviting, and comfortable. My kids had a blast too. Definitely recommend staying here!
Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 341 reviews

Modern Upstate Cabin, near Rhinebeck NY

ErinRating, 5 stars1 week ago
Hands down the best Airbnb of the 25+ airbnbs I’ve ever stayed in. We didn’t want to leave! This place is so special and restorative. We can’t wait to go back. Tina is a super special host too. Her heart is invested in your experience and you can feel how much she wants you to treasure Maitopia as much as she does.
Guest favorite

Home in Saugerties

4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars2 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 near Ski & Dining

AllisonRating, 5 stars1 month 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

Home in Litchfield

4.93 out of 5 average rating, 179 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

MelissaRating, 5 stars1 month ago
Sweetbrier Farm was the perfect place to spend Thanksgiving. The house is beautiful inside and out, well-equipped for home cooking, and extremely cozy with an amazing fireplace that provided hours of cozy lounge time. We would love to return in the summer months as the outside areas and sun porch are so inviting! Would recommend Elizabeth's place to anyone looking for a fun, yet peaceful New England getaway.

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    $150 before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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