Family-friendly vacation rentals in Sheffield

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Sheffield 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 stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.
Farm stay in Kent
4.87 out of 5 average rating, 319 reviews

(°) The Wandering Peacock (°)

MikaylaRating, 5 stars5 days ago
Abigail is an incredible host. She is super accommodating and communicative. She is the sweetest and her home is incredible. This place is definitely worth it. Beautiful space and a wonderful experience.
Guest favorite
An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars3 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Superhost
A cabin exterior features large glass windows revealing a cozy sleeping area adorned with soft bedding. A pendant light illuminates the space, offering a warm glow. Lush greenery and colorful flowers line the path leading to the cabin, enhancing the natural setting.
Cabin in Saugerties
4.81 out of 5 average rating, 264 reviews

Container Cabin in the Catskills (Field)

CynthiaRating, 5 stars1 week ago
Choosing to stay in Porter's container cabin was the best decision we could have made for our vacation. It was so peaceful and relaxing. We had daily visits from a beautiful deer, and countless butterflies. We chose to use this time to unplug, and really connect with each other, and we could not have chosen a better place to spend our time. We've missed the view from the front door every day since we've left, and we're already planning to come back next year. Thank you so much for having us.
Top guest favorite
A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.
Home in Colebrook
4.99 out of 5 average rating, 224 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

MichaelRating, 5 stars1 month ago
Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.
Guest favorite
A red guest house is nestled among tall trees in a woodland setting. Large windows allow natural light to fill the interior, while the surrounding forest provides a serene backdrop. Leafy undergrowth and a carpet of dried leaves cover the ground in front of the house.
Home in Red Hook
4.88 out of 5 average rating, 234 reviews

Wooded Retreat w/ Hot Tub and Trout River

DanicaRating, 5 stars2 weeks ago
Just what we needed for a relaxing weekend. Place was clean and comfortable. Situated in the woods- scenic, quiet and relaxing with the sound of the creek down below. Rainy weekend but it was dreamy looking out the large floor to ceiling windows. Highly recommend this place if youre looking for a quiet getaway. Rhinebeck Village and Red Hook shops are within 20-30 min drive.
Superhost
A scenic view of a two-story cottage surrounded by lush greenery. The well-maintained garden features various plants and flowers. A fenced yard offers a sense of privacy, with a pathway leading to the entrance. The structure displays a blend of traditional and modern architectural elements.
Home in Woodstock
4.93 out of 5 average rating, 930 reviews

1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole

GabrielleRating, 5 stars3 weeks ago
Jonathan’s place was fantastic! Location felt like a secluded oasis, but was only 5 mins to town. Everything was clean, hot tub and sauna included. Our pups greatly appreciated running around in the fenced in yard. Jonathan was quick to respond the one time we messaged. Would absolutely stay there again!
Guest favorite
A charming farmhouse is nestled among lush trees, featuring a mix of white siding and red brick accents. The inviting entrance is framed by greenery, while a spacious yard provides a serene setting, perfect for relaxation and exploration.
Home in Craryville
4.92 out of 5 average rating, 237 reviews

The City Farmers Upstate. Farm house with hot tub

JocelynRating, 5 stars3 weeks ago
We loved staying at Anat’s gorgeous home. We’ve been in many spots in the HRV and even Columbia County, but this stood out for being so tranquil and for having such lovely grounds. We enjoyed the Copake Hillsdale Farmers Market and a great meals at Local 111 and Zinneas. Cooking at the house was a breeze and there were more than enough beds and living spaces for our two families to feel so comfortable. Hot tub was lovely! We can’t wait to return.

Family- and pet-friendly home rentals

Top guest favorite
A two-story house showcases a welcoming front porch with hanging flower pots. The lawn is well-kept and bordered by garden beds. The exterior features a blend of white and muted green siding, with prominent green shutters on the upper windows.
Home in Millerton
4.9 out of 5 average rating, 157 reviews

The 1913 House, book 6 days get the 7th free.

BenRating, 5 stars3 weeks ago
My wife and I had a great time. Amazing house right outside of town. Huge yard which our dog loved! Hopefully we will be back.
Top guest favorite
A serene pond reflects the cloudy sky, surrounded by lush greenery and tall grasses. The still water enhances the tranquil atmosphere of the landscape, with distant buildings nestled among the trees, completing the rural setting.
Guesthouse in Stephentown
5 out of 5 average rating, 416 reviews

Dog Friendly Studio

LilyRating, 5 stars2 weeks ago
We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!
Guest favorite
A circular stone entryway frames a winding path leading to a quaint cabin nestled among tall trees. Sunlight filters through the forest canopy, casting a gentle glow on the surrounding greenery.
Guesthouse in Lenox
4.93 out of 5 average rating, 105 reviews

The East Street Cabin

PeterRating, 5 stars8 months ago
We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA
Guest favorite
A serene lake is surrounded by lush green hills, reflecting the clear blue sky. The water is calm, with a small rowboat visible in the distance, adding to the tranquil outdoor setting.
Home in Ancram
4.99 out of 5 average rating, 181 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

AdelyaRating, 5 stars1 month ago
The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!
Guest favorite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 355 reviews

Be in Nature at this Gorgeous Riverfront Cabin

AaryaRating, 5 stars4 days ago
We loved the place, it was a beautiful home with lots of light and accessible green space. It was perfect for a short getaway. It’s a short drive from nearby towns and was very easy to find based on the directions. Mark was a responsive and accommodating host and we had a wonderful time in his airbnb.
Guest favorite
A cozy living area features a comfortable sofa facing a television and a wood stove with a glass front. The space is illuminated by natural light from large windows, complemented by rustic wooden beams and a warm wood floor. A round coffee table adds functionality.
Cabin in Ghent
4.91 out of 5 average rating, 288 reviews

Guesthouse on beautiful property, close to Hudson

KaitlynRating, 5 stars3 weeks ago
The guesthouse was so dreamy! We had a wonderful stay, the hosts were super friendly, and we loved meeting their sweet dogs. The house was close to great restaurants and shops in Hudson, Kinderhook, and Ghent, as well as hiking trails. The lovely trail on the property was a great bonus, one we took advantage of 4 times throughout the weekend :). Would definitely visit again!
Superhost
The open living and dining area features exposed wooden beams and large windows allowing natural light. A communal table is surrounded by candles, while a cozy seating area with bookshelves, artwork, and decorative accents invites relaxation.
Home in Ancram
4.81 out of 5 average rating, 113 reviews

Secluded Post-And-Beam Retreat

SarahRating, 5 stars4 months ago
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.
Guest favorite
The spacious living and dining area features a fieldstone fireplace as a focal point. Exposed beams add character, while colorful hanging lamps brighten the space. A large wooden dining table is surrounded by sleek chairs, and cozy seating areas are arranged for relaxation.
Home in East Durham
4.93 out of 5 average rating, 248 reviews

Bluff House

ChuckRating, 5 stars3 weeks ago
We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!

Family-friendly home rentals with a pool

Top guest favorite
A large kidney-shaped pool reflects the clear blue sky, bordered by a spacious patio area. The two-story brick home with teal doors and large windows is visible in the background, surrounded by lush greenery and a fence for added privacy.
Chalet in Catskill
4.96 out of 5 average rating, 195 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

WhitneyRating, 5 stars5 days ago
We had a magical weekend away and our stay was everything we hoped it would be, and more. Olia was incredibly responsive, friendly, and all around wonderful to connect with. The house was a magical time capsule holding the best of energy and a glimpse into the 70s - so fun. The pool and patio were awesome, with open and friendly spaces inside too, all made for the best of entertaining spaces. We could not have asked for a better weekend away, and we cannot wait to plan our next trip! Thank you!
Guest favorite
Apartment in Earlton
4.93 out of 5 average rating, 296 reviews

Sweet Farm Stay

AmyRating, 5 stars1 month ago
This is our fifth year coming to the farm. Larissa is absolutely masterful with kids of all ages (even tough kids). My daughter races out at 9 am to do farm chores and begs for more (and this is a kid who drags her feet doing chores at home)!! We love the rhythm of farm and find it really easy to disconnect and unwind. After chores in the morning, you're welcome to spend as much time as you want with the animals, which is a real treat. Whether it's feeding the horses hay, sharing food scraps with the goats, or watching the chickens do their evening routine, there's so much to enjoy. The local towns are lovely, but if you like the farm experience, you may never leave the property. Larissa is incredibly knowledgeable and generous in sharing her experience and expertise. She has created an absolutely magical environment, and I would highly recommend visiting!!
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 outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars8 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!
Guest favorite
A view of the outdoor space features a wooden gazebo alongside a landscaped area with small flower beds. An above-ground swimming pool is visible in the background, surrounded by greenery. The entrance of the apartment is seen adjacent to the garden area, providing a welcoming atmosphere.
Guest suite in New Paltz
4.84 out of 5 average rating, 194 reviews

Private apartment in rural home

ChristaRating, 5 stars3 weeks ago
I stayed in this apartment for a month and loved it. The location is gorgeous, the apartment is a great size for the price, the hosts are just truly lovely people who made me feel totally welcome. You will hear the ceiling creak when they walk around above you in the main house and the dogs bark, but not alot and the owners are very quick to quiet them down. I slept so well there. I never felt awkward sitting outside admiring the flowers and the trees, even when Sherrill and Clark were going about their yard chores. I loved being greeted when I arrived and sent off when I left. I felt like I truly mattered as a guest and a person. This is what airbnb hospitality should be! Thank you!! I'd stay again and highly recommend.
Guest favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favorite
An inviting in-ground heated swimming pool is surrounded by a spacious stone patio, featuring six lounge chairs and a circular dining table with four chairs. A large umbrella provides shade, and a red barn is visible in the background, framed by greenery.
Home in Saugerties
4.94 out of 5 average rating, 144 reviews

5BR close to Village | Diamond Mills | HITS | Pool

JimenaRating, 5 stars3 weeks ago
We had a great time at Saugerties! Rebecca's house was wonderful. The heated pool and the trampoline were the kids' favorite and they kept them entertained all day. The adults enjoyed the shade under the comfy pool lounge chairs & the spacious deck furniture. The backyard of the house was well kept and equipped so we spent a lot of time outside. The house is very well equipped and it was spacious for 2 families of 4. Everything was functioning well. The house is close to downtown and there are plenty of things to do nearby. Host was super quick to respond back and to help with whatever we needed right away. We def recommend Rebecca's house.
Guest favorite
A modern farmhouse exterior is visible beside a crystal-clear swimming pool surrounded by grassy areas. Colorful pool floats are placed in the water, while a wooden fence and tall trees frame the peaceful setting.
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars8 months ago
We had a terrific stay. The house was exactly as advertised.

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

  • Total rentals

    60 properties

  • Nightly prices starting at

    G$20,898 GYD before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 properties include access to wifi

Destinations to explore