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

Top guest favorite
A bright living area features a comfortable seating arrangement and large windows that allow natural light to fill the space. A wood-burning stove is positioned in the corner, and an easel displays a vibrant painting. A plush rug adds warmth to the wood floor.
Home in Craryville
4.98 out of 5 average rating, 221 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

DavidRating, 5 stars2 weeks ago
Three adults and a toddler spent four great days at Myrhah’s house in Craryville. I have very little to add to all the other enthusiastically positive reviews. They are totally accurate.I will note that one of us is a pastry chef who was at home in Myrhah’s kitchen. It’s stocked with quite a few good baking tools. Another member of our group is a 19-month old toddler who loved the toys and big airy spaces for play. We all enjoyed the home’s aesthetic and appreciated Myrhah’s responsiveness and warmth. I wished we could have stayed longer.
Guest favorite
A modern house is surrounded by trees with colorful autumn leaves. The exterior features a wraparound deck, and snow lightly covers the ground and plants. Clear blue skies enhance the peaceful outdoor setting, creating a serene atmosphere.
Home in Rhinebeck
4.92 out of 5 average rating, 237 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

SandyRating, 5 stars3 weeks ago
Loved this house! We have stayed in many places all over the world for both business and pleasure. This was a business trip. House was great, location was great. It was cold and rainy so we didn’t get to enjoy the porch, deck or hot tub . Even without these amenities we totally enjoyed the house. Hoping to stay again next time we are in the area. We are in Rhinebeck twice a year for the antiques show in the Fairgrounds . Instructions on house were easy to understand and concise. Great job guys!
Top guest favorite
A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. It offers expansive views of the natural landscape, with gentle hills visible in the distance under a soft, overcast sky.
Apartment in New Paltz
4.97 out of 5 average rating, 544 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

LacieRating, 5 stars4 weeks ago
Ami’s place was great! Stayed for my birthday and was surprised with a delicious tres leche cake upon my arrival! The view was incredible, amenities were amazing, overall it was everything I hoped for and more. Thanks Ami!
Superhost
A bright living area features large windows that allow natural light to illuminate a pink sectional sofa adorned with colorful cushions. A white coffee table sits atop a light wooden floor, complemented by a decorative rug. Art pieces in warm hues are displayed on the wall.
Home in Olivebridge
4.92 out of 5 average rating, 458 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

AmeliaRating, 5 stars1 month ago
We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!
Guest favorite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring
4.95 out of 5 average rating, 324 reviews

Hilltop Hideaway Forest Villa on 13 acres!

RebeccaRating, 5 stars2 weeks ago
My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!
Top guest favorite
A cozy living area features a stone fireplace with a warm fire, surrounded by wooden cabinetry and appliances. Brightly colored striped couches flank a wooden coffee table, while natural light streams in through a large window. Pendant lights add an inviting glow to the space.
Home in Ancramdale
4.94 out of 5 average rating, 142 reviews

Unwind in the country, stargaze in hot tub

OliviaRating, 5 stars4 months ago
What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.
Guest favorite
The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.
Guesthouse in Beacon
4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

AnthonyRating, 5 stars1 week ago
My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.
Guest favorite
A spacious living area is furnished with a large sectional sofa, adorned with decorative throw pillows. Natural light filters through multiple tall windows, illuminating a central coffee table accompanied by simple decor. In the background, a large dining table and green accents enhance the inviting atmosphere.
Home in High Falls
4.96 out of 5 average rating, 217 reviews

Clove Schoolhouse on Mohonk Preserve

PaulRating, 5 stars2 days ago
We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.

Family- and pet-friendly home rentals

Guest favorite
An exterior view of an old milk barn, featuring a wooden door and overgrown greenery surrounding the structure. The rustic charm is highlighted by exposed brick and an angled roof. A few outdoor furniture pieces are positioned nearby, complementing the natural setting.
Farm stay in High Falls
4.87 out of 5 average rating, 945 reviews

Dave's Milk Barn

ClaraRating, 5 stars3 weeks ago
We loved our stay at this beautiful, charming, and peaceful barn. The space was cozy and thoughtfully designed—perfect for a relaxing staycation. The property itself is beautiful, and it’s just a short drive to great hikes, bike trails, restaurants, and breweries. A truly lovely spot to unwind and explore. Thank you for such a wonderful experience!
Guest favorite
A Mediterranean style house is showcased against a backdrop of rolling hills and the Hudson River. The exterior features multiple windows, and a stone chimney rises from the roof. The expansive landscape is highlighted by autumn foliage, creating a vibrant setting.
Home in Garrison
4.93 out of 5 average rating, 162 reviews

Hudson Valley Mountaintop Riverview

JacquelynRating, 5 stars3 weeks ago
Mahmoud was a wonderful host. Very responsive, pleasant, and helpful. His home and the views were spectacular, and the koi pond was beautiful. It’s a great location to stay while visiting West Point, as it’s a quick drive across the Bear Mountain Bridge. Our large group felt comfortable and welcomed. One of the bedroom descriptions could have been listed a little clearer because you need to pass through the master bedroom to get to it. Luckily our family was ok with that. We would stay again.
Guest favorite
A blue-brick exterior is complemented by a landscaped yard featuring two lounge chairs with light blue cushions. A dining area with an umbrella sits adjacent to the building, while stone pathways lead to the entrance flanked by greenery.
Home in Warren
4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

DemianRating, 5 stars6 months ago
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend
Top guest favorite
The exterior of a modern wooden house is surrounded by lush greenery. Large windows allow natural light to fill the interior. A neat lawn leads to the entrance, which is framed by manicured bushes and trees in the background.
Home in Millbrook
5 out of 5 average rating, 115 reviews

Stunning Views, Light and Open - The Beech House

BobbiRating, 5 stars3 weeks ago
We lived in the Hudson Valley before retiring to Maine. For the past 4 years, Sarah and Jonathan’s home has provided the perfect spot for return visits with family and friends and a comfortable place away from home. The house is tastefully decorated and provides all that we require for an extended stay. The kitchen is well appointed with utensils, dishware, pans, and a large assortment of appliances. A special feature in the home is the lower level room with a huge wrap-around couch, large screen tv and toys for the kids. In addition, the grounds are beautiful. The outside deck allows for time to enjoy the gorgeous view and the large yard is fun for romps with our little Havanese. Being close to the town is an added bonus: The Tribute Gardens, Marona’s Market, the little French restaurant (Cafe Les Beaux), Stewart’s for ice cream, The Merritt Bookstore + Toystore, various antique shops are places we frequent. Innisfree Gardens and Dover Stone Church are nearby. We love it here!
Top guest favorite
A rustic farmhouse exterior showcases a wooden façade with red double doors and a welcoming balcony adorned with potted flowers. The balcony is accessed by wooden steps, leading to a charming outdoor seating area. Seasonal foliage decorates the surrounding landscape.
Farm stay in West Simsbury
4.96 out of 5 average rating, 487 reviews

Flamig Farm Staycation

CassandraRating, 5 stars1 week ago
I almost didn’t want to write a review so people don’t book this place…. But I definitely have to. It was such a blast. We collected eggs in the morning, we tried peacock eggs for breakfast. They had an amazing playground, and awesome cats and dogs running around the farm. The fact that we got the farm to ourselves after hours was so memorable. My first airbnb and probably will put other airbnbs expectations high.
Top guest favorite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Apartment in Ossining
4.96 out of 5 average rating, 439 reviews

Hudson River Peaceful Getaway, Explore from here

AlexisRating, 5 stars1 week ago
Dan & Jill’s home was beyond beautiful and comfy. It was very easy to find, private and felt safe. The inside of the home was more spacious than expected and extremely clean. The panoramic views from all windows was truly a treat. The hosts were very thoughtful and sweet. If you forgot to pack something, they most likely had it. Check in was smooth, stores/supermarket was a 3 min drive. 0 complaints and cannot wait to stay again!
Guest favorite
A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.
Cabin in Sterling Forest
4.96 out of 5 average rating, 428 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

Maire Rating, 5 stars4 weeks ago
“Cabinesse” host (s), clearly care about their cabin and their guest. The cabin is sparkly clean and comfortable. The lake views are beautiful. The host is responsive and very helpful. We followed some suggestions from the guest book, such as a visit to Warwick, Bellvale Farms Creamery for amazing ice cream and Appalachian Pochuck Boardwalk Trail. We also tried the Bellvale Market (everything made there; amazing food) and hiked the Sterling Lake Loop (4.2 miles). Amazing unplug! Highly recommended.
Guest favorite
A sweeping view of the Hudson River framed by vibrant autumn foliage. The landscape showcases a mix of red, orange, and yellow trees with hills in the background, creating a tranquil natural setting. Mist softly blankets the distant mountains.
Guest suite in Fort Montgomery
4.94 out of 5 average rating, 466 reviews

West Point - Mountain Top Suite

SusanRating, 5 stars1 month ago
Yi's Place is a cute cottage style with tons of old charm, the view is breathtaking and exquisite. You need to really like vintage retro home style and appreciate nature to appreciate the stay. The host is very thoughtful and provides everything needed for the stay.

Family-friendly home rentals with a pool

Top guest favorite
A swimming pool is set in a lush green yard, surrounded by trees and flowering plants. Comfortable lounge chairs are positioned nearby, while a large rock adds a natural element to the pool area. The property's main house stands in the background, completing the inviting scene.
Barn in Bethel
4.98 out of 5 average rating, 237 reviews

Escape to a Restored New England Antique Milk Barn

GavinRating, 5 stars3 weeks ago
My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.
Top guest favorite
Home in New Paltz
4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

EleonoraRating, 5 stars3 weeks ago
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Top guest favorite
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 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 favorite
The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.
Cabin in Red Hook
4.96 out of 5 average rating, 353 reviews

Modern Upstate Cabin, near Rhinebeck NY

JenniferRating, 5 stars1 week ago
Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars2 weeks ago
Only complaint would be the noise from road during the morning commute
Guest favorite
A scenic aerial view showcases an outdoor pool surrounded by greenery, with mountain vistas in the background. Lounge chairs line the poolside, inviting relaxation. The property features a blend of manicured gardens and natural landscaping, creating a peaceful environment.
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 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 favorite
A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.
Home in Kerhonkson
4.95 out of 5 average rating, 363 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

SophieRating, 5 stars1 week ago
We had a beautiful stay in Kerhonkson for a relaxing bachelorette weekend! Lillian’s place is absolutely beautiful and was so comfortable for my friends and I. Everything was as described, extremely clean, plenty of linens and had everything we needed in the kitchen to cook a few meals. We enjoyed sitting by the pool when it was sunny. Lillian was very communicative and flexible with check in time. Thank you!

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$27,188 GYD 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

  • Wifi availability

    40 properties include access to wifi

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