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Family-friendly vacation rentals in Sheffield

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Top-rated family-friendly rentals in Sheffield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An exterior view of the renovated red barn features a sloped roof and white-trimmed windows. Two white Adirondack chairs adorned with pink cushions are positioned on the grass, under the shade of a nearby tree, providing a cozy outdoor seating area.

Loft in Great Barrington

4.99 out of 5 average rating, 332 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

4.94 out of 5 average rating, 417 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favorite

A serene sleeping area is present, featuring a spacious bed adorned with a patterned duvet. Large windows frame the view of the surrounding trees, inviting natural light into the space. A small bookshelf stands in the corner, complementing the wooden floors and walls.

Cabin in Cummington

4.98 out of 5 average rating, 214 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Top guest favorite

A well-lit bedroom features a spacious bed with crisp white bedding and a decorative throw. A sliding glass door leads to a patio area, framed by light curtains. Minimalist shelving holds decorative items, and a fan is positioned beside the bed.

Guest suite in Great Barrington

4.98 out of 5 average rating, 107 reviews

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 118 reviews

Perfect Peaceful Berkshire Location !

We have two rentals. Only one rental is rented at a time. This rental has 2 bedrooms, a fully equipped kitchen and is super clean. (THE 1 BEDROOM LISTING is called “Great Berkshire Getaway”) Conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit

Top guest favorite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

4.96 out of 5 average rating, 353 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

A wooden rocking chair sits on a quaint porch, next to vibrant flower pots filled with blooming plants. Green grasses and a hint of autumn foliage create a serene outdoor setting, inviting relaxation and peaceful moments.

Cottage in New Lebanon

4.95 out of 5 average rating, 193 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

A loft-style bedroom is visible, featuring a spacious bed with white linens. Two windows allow natural light to brighten the room, complemented by a modern ceiling fan. A decorative lantern hangs above, and a wood-paneled railing leads down to the staircase.

Guesthouse in New Marlborough

4.9 out of 5 average rating, 199 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

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

This peaceful home is in the middle of nowhere, yet conveniently close to it all: Bash Bish Falls (10 mins), Millerton (10 mins), Copake Lake (15 mins), Catamount Mtn (20 mins), Lakeville, Conn. (20 mins), Hudson, NY & Great Barrington, Mass. (30 mins). For those who'd prefer to read by the fire or stargaze from the hot tub, this home is a destination in and of itself. Luxuriously comfortable beds plus all the amenities offer a restful retreat from busy lives.

A private deck offers a serene view of the sunset over the mountains, framed by lush greenery. Two lounge chairs provide a comfortable spot for relaxation, and a small table sits nearby adorned with a vibrant flower arrangement.

Guest suite in Millerton

4.93 out of 5 average rating, 368 reviews

Sunset 60 mile view

ROMANTIC LUXURY! Spring has SPRUNG! Gorgeous warm weather; fresh, crisp mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, charcoal bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV.

Top guest favorite

A spacious studio apartment is displayed with natural light streaming through large windows. A comfortable narrow futon and a cozy seating area are visible, along with a dining table surrounded by wooden chairs. A door leads to the private deck, enhancing the overall openness.

Apartment in Sandisfield

4.92 out of 5 average rating, 235 reviews

Sunny Berkshire Studio Apartment

Sunny many windowed studio apartment attached at west end of the main house. Self contained with kitchen and bathroom. Plus addition sleeping area (attached bedroom). Studio and bedroom have full size beds Studio also has narrow twin futon. 1 mile long gravel road for a "walk out the door and go" wake up morning hike. State forest is across from house, along Bosworth Road and along Rt 57. Long Term Guests welcome. $5/guest after 2.

A charming shingled farmhouse is surrounded by lush greenery and colorful flowering plants. The stone walkway leads to the welcoming front porch. Tall trees provide shade, while a skylight enhances the natural lighting on the upper level.

Home in Egremont

4.94 out of 5 average rating, 281 reviews

Modern Farm House 5 minutes from Great Barrington

Completely renovated with absolute style, this shingled farmhouse boasts clean modern decor with the architectural charm of a country home. Spacious & sunny kitchen that connects to the large outdoor patio with fireplace. Cozy living room with large flat screen television for streaming Netflix & Amazon. First floor bedroom with bathroom & laundry. The second floor master suite has cathedral ceilings & a jet powered glass shower.

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Popular amenities for Sheffield family-friendly rentals

Free parking on premises

Air conditioning

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

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 (°)

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

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)

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

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

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

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

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.

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

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

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.

4.99 out of 5 average rating, 181 reviews

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

Cottage in Poughkeepsie

4.91 out of 5 average rating, 355 reviews

Be in Nature at this Gorgeous Riverfront Cabin

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.

4.91 out of 5 average rating, 288 reviews

Guesthouse on beautiful property, close to Hudson

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.

4.81 out of 5 average rating, 113 reviews

Secluded Post-And-Beam Retreat

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

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

Apartment in Earlton

4.93 out of 5 average rating, 296 reviews

Sweet Farm Stay

Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

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

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

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.

4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

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

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

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