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

A bright entryway features a white wall with hooks for hanging items and a woven basket atop a built-in bench. Light enters through a nearby window, illuminating the space. A simple blue area rug adds a touch of color, and a door leads outside.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Top guest favorite

Home in Ancram

4.99 out of 5 average rating, 178 reviews

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

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Superhost

A backyard playset is situated on lush green grass, featuring a swing set with two swings and a slide. A small playhouse with a sloped roof can be seen nearby, surrounded by trees providing a natural and shaded environment.

Home in Otis

4.94 out of 5 average rating, 144 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in the Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

Guest favorite

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, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. 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!

Guest favorite

A charming two-story house features a welcoming porch bordered by colorful flower beds. Blue trim accents the white exterior, highlighting the architectural details. A pathway leads to the entrance, which is framed by a decorative arch and supported by columns.

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.

Cabin in Hillsdale

4.9 out of 5 average rating, 105 reviews

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Guest favorite

A spacious living area displays a mix of seating options, including a blue couch and two accent chairs. Natural light filters through large windows, highlighting the wooden beams above. A wooden table sits in the foreground, with a ladder leading to the loft visible in the background.

Apartment in Earlton

4.93 out of 5 average rating, 294 reviews

Sweet Farm Stay

Come stay in a fully-outfitted barn apartment with views that look out over the pony paddock and the sheep pasture! For an extra fee we also offer… ** FARM CAMP** perfect for kids & families. 2 hours of farm chores, pony-riding, crafts every morning that you are here. ** CRAFT RETREATS** All-inclusive weekend with up to 7 guests. Wool / wood / kitchen craft. Work on the farm, MAKE stuff, and enjoy the outdoors. DM for more info. Find us on ig — honeyhollowfarmstay!

Guest favorite

The living area features two woven armchairs with light cushions positioned beside a decorative side table. Natural light filters through the nearby window, illuminating the room. A fireplace is visible in the background, contributing to a cozy ambiance.

Home in Litchfield

4.98 out of 5 average rating, 232 reviews

Storybook Cape...HOST & Co.

A classic 1930’s Cape Cod home located in the beautiful Litchfield Hills. Litchfield Green is a five minute drive where you can enjoy antiquing, dining, shopping, and relaxing in the picturesque town center. If hiking and outdoor activities are more your thing we are also minutes from White Memorial Foundation and Topsmead National Forest is right around the corner. Mohawk Mountain Ski Area is 12 miles away.

Top guest favorite

A spacious living room features two couches, a daybed, and a work desk with an office chair. Natural light fills the room through a large window, highlighting decorative plants. Soft lighting from various lamps creates a comfortable ambiance against warm wooden floors.

Home in Saugerties

4.99 out of 5 average rating, 142 reviews

Saugerties Village Retreat

Charming Village home located 5 minutes from Hits. Walking distance to village restaurants & shopping. Front porch, Private backyard with deck and patio. Large eat in kitchen with separate dining room. Spacious Living room with 2 couches and daybed. Cable TV & Wifi Driveway & street parking for up to 3 cars. washer, dryer, dishwasher . Fully fenced in yard for up to 2 dogs with pre approval from host.

Guest favorite

An open kitchen and dining area is visible, featuring wooden beams and a modern design. A spacious dining table is surrounded by wooden chairs. Stainless steel appliances complement the kitchen cabinetry, and natural light enters through small windows above.

Cottage in Copake Falls

4.91 out of 5 average rating, 353 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Top guest favorite

Natural light filters through large windows into an open hallway featuring warm wood flooring. A wooden staircase leads to the lower level, while a modern kitchen is visible through an archway, accented by a decorative wall element.

Home in Egremont

4.98 out of 5 average rating, 135 reviews

A sunny, quiet chalet beautifully decorated.

Welcome to our modern and sunny chalet nestled in the woods. Located directly across the street from Catamount Mountain Resort for year-round fun. Numerous hiking trails nearby, and Great Barrington’s dining and shopping minutes away. Relax in style and comfort and make unforgettable memories with friends and family. Please not that we do not allow pets.

Superhost

The cabin's exterior is surrounded by lush greenery, showcasing wooden siding and a well-maintained deck. Outdoor seating is provided on raised steps, while a patio area features a small table and chairs. An umbrella offers shade for relaxation during sunny days.

Cabin in Otis

4.86 out of 5 average rating, 416 reviews

Cozy cabin in the Berkshires

UPDATE: We have broadband!! Cozy and peaceful Scandinavian inspired post and beam cabin. simple, unfussy. Near many wonderful Berkshires activities. Minutes from Jacobs Pillow, lakes, ponds, hiking, biking, skiing. amazing local food and farms. Perfect country retreat for a weekend, a week or the whole month. sleeps up to 4.