Family-friendly vacation rentals in New Marlborough

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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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Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 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.

May 13 – 20

R2,865 ZAR per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 350 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

Apr 16 – 23

R7,206 ZAR per night

Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 202 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.

Apr 2 – 9

R4,406 ZAR per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 258 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Oct 5 – 12

R2,339 ZAR per night

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Mar 22 – 29

R2,471 ZAR per night

Guest favorite

Home in Chester

4.96 out of 5 average rating, 311 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Dec 7 – 14

R3,512 ZAR per night

Guest favorite

Home in Sheffield

4.9 out of 5 average rating, 107 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Berkshire Blend coffee/decaf, teas, milk, sugar and juice are a first morning welcome gift. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Jun 22 – 29

R3,219 ZAR per night

Guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 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!

Aug 21 – 28

R3,086 ZAR per night

Guest favorite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 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. PET FEE: $25/stay

Nov 22 – 29

R2,218 ZAR per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 340 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.

Mar 14 – 21

R1,883 ZAR per night

Guest favorite

Cottage in Copake Falls

4.91 out of 5 average rating, 317 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.

Nov 7 – 14

R3,149 ZAR per night

Superhost

Cabin in Otis

4.87 out of 5 average rating, 402 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.

Sep 5 – 12

R3,404 ZAR per night