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Family-friendly vacation rentals in New Marlborough

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in New Marlborough

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, 334 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.

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

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

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, 418 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 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, 108 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, 119 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, 354 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 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 spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.

Cabin in Monterey

4.95 out of 5 average rating, 282 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Top guest favorite

The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.

4.95 out of 5 average rating, 163 reviews

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

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.

A bright and inviting living room features a floral-patterned couch and large windows adorned with green curtains. Decorative plant stands filled with various plants enhance the space, while a stained glass light fixture casts a warm glow over the area. A cozy atmosphere is created with soft lighting.

Apartment in Winchester

4.91 out of 5 average rating, 382 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

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Popular amenities for New Marlborough 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, 222 reviews

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

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, 546 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

An 8-person hot tub bubbles gently under the night sky, surrounded by trees. A scenic trail, lined with colorful lights, winds through the woods leading toward a well-lit deck. The inviting ambiance is set for relaxation and exploration.

Bungalow in Easthampton

4.92 out of 5 average rating, 505 reviews

The Creation Station

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, 320 reviews

(°) The Wandering Peacock (°)

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

A charming farmhouse is depicted, featuring a white exterior and a welcoming red front door. Windows provide natural light, and a wood pile is neatly stacked beside the entrance. Lush greenery and seasonal foliage surround the home, set against a clear blue sky.

Home in Northampton

4.88 out of 5 average rating, 639 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

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, 153 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, 266 reviews

Container Cabin in the Catskills (Field)

Family- and pet-friendly home rentals

Home in Great Barrington

4.95 out of 5 average rating, 128 reviews

The Hideaway: Berkshire Home - village of Egremont

A charming cottage is nestled within a grove of cedar trees, featuring a welcoming white exterior and a central stone chimney. Lush green grass surrounds the property, enhancing the secluded atmosphere and inviting tranquility.

Cottage in West Camp

4.93 out of 5 average rating, 123 reviews

Hudson Valley Cottage

A chandelier with crystal accents hangs above a bed, illuminating the space. Large mirrors reflect soft light, and a delicate orchid in the foreground adds a touch of nature. Neutral tones and elegant décor create a harmonious and inviting sleeping area.

Home in Millerton

4.92 out of 5 average rating, 409 reviews

Skyloft,25 Acres, self check in, 500 meg wifi

A spacious living area features a large sectional couch surrounding a coffee table, with a stone fireplace serving as a focal point. Natural light enters through multiple windows, highlighting the open floor plan and wooden elements throughout the space.

4.94 out of 5 average rating, 145 reviews

Berkshires hideaway! Hikes & serenity near lake

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

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, 490 reviews

Flamig Farm Staycation

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, 196 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 491 reviews

midcentury mod * POOL * walk out trail to mohonk

Top guest favorite

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

Home in Saugerties

4.94 out of 5 average rating, 131 reviews

Bluestone Escape - Where everyone is at 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, 145 reviews

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

An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.

Apartment in Glastonbury

4.9 out of 5 average rating, 439 reviews

Quiet 2 bed room apt w/ private entrance.

Home in Litchfield

4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

A serene swimming pool is surrounded by tall greenery, offering a tranquil escape. The crystal-clear water reflects sunlight, inviting relaxation. A decorative statue is visible in the background, enhancing the peaceful atmosphere of the outdoor space.

Apartment in Northampton

4.97 out of 5 average rating, 372 reviews

1880s sun-bathed beauty in best downtown location

Quick stats about vacation rentals that are family-friendly in New Marlborough

Total rentals
50 properties
Nightly prices starting at
G$29,286 GYD before taxes and fees
Total number of reviews
1.7K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi

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