Family-friendly vacation rentals in Great Barrington

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Great Barrington

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

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Top guest favorite

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

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)

Superhost

Home in Egremont

4.95 out of 5 average rating, 108 reviews

Bucolic Berkshires House

UNIQUE, bright, open space with a great kitchen and thoughtfully decorated. Near MANY exciting destinations such as skiing, cultural and arts destinations, vineyards, antiquing, you name it, in both the Berkshires and Hudson Valley. Located on an unpaved road and adjacent to a beautiful park and a nearby lake. There's so much to do, but if you'd prefer to take a more relaxed approach to your get-away then shop the wonderful local food stores and farms and enjoy cooking and our lovely house.

Guest favorite

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

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

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

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

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.

Top guest favorite

Cottage in Staatsburg

4.91 out of 5 average rating, 193 reviews

Charming Creek side Getaway 3.5 mi. from Omega

Nestled in a creek side hollow, this private and cozy cottage offers a welcoming space to relax and refresh in. The house has a charm all its own, featuring beautiful furnished rooms with the accent on comfortable. Combine that with the creek side setting without another visible house from the property and it truly feels like a "nature's getaway".

Top guest favorite

Home in Averill Park

4.96 out of 5 average rating, 159 reviews

Cozy, peaceful lake house close to Jiminy Peak

My fabulous, peaceful lake house is located on beautiful quiet 3rd Burden Lake complete with a large private porch, dock, a canoe and one kayak. The house has incredible views throughout . Great kayaking, hiking, fishing,close to MASS MOCA. 25 minutes to Troy, Chatham and Albany. Very close to Jimney Peak for skiing in the wintertime.

Superhost

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.

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What guests are saying

Lake House in Averill Park, NY (age 30+ excl kids)

4.98 out of 5 average rating, 174 reviews3 weeks ago

First of all, a 1 o’clock check in started us off on a very happy note. Then, having room for each female to have her own bed made a for peaceful stay. The biggest thing was how much the space was warm, comforting, and full of character. The sliders provided a broad view of the lake. The kitchen with the open area to dining and front area provided an open concept feel to an older home while maintaining its true character. The tall cabinets contained every utensil/small appliance that we needed and more. We brought a bag of board games as we know what we like, but there was a great variety already there. While there was plenty of room, we felt “together” in that space. We can only imagine the beauty that arrives later in spring. Thank you for having us!

Home in Averill Park

What guests are saying

Farmington River Carriage House Pleasant Valley CT

4.89 out of 5 average rating, 97 reviews5 months ago

We had a beautiful, peaceful stay at Bruce and Cheryl's guest home. The space was perfect for my toddler to run around in the yard, the accomodations were cozy and quiet, and our hosts were very gracious. Bruce built us a fire in the fire pit overlooking the river one evening. It was incredibly beautiful! If you have an EV, there is a convenient Tesla charger on site. The property is only a short walk away from a state park with miles of hiking trails. We would definitely like to go back for another stay!

Guesthouse in Barkhamsted

What guests are saying

Greek Revival Farmhouse

4.97 out of 5 average rating, 110 reviews2 months ago

Michelle was incredibly gracious and responsive when we called late after our check in with a question about the heater. The place is gorgeous and you can tell that she pays attention to every detail and is doing all she can to make it a pleasant stay. The decor is perfect, the amenities are perfect. We had plenty of room to cook and host a dinner with four adults and two kids. We lit a fire, played games and relaxed. The bedding is so comfortable and we all slept so well.

Home in Stockbridge

What guests are saying

2 blocks to Warren w parkin bb

4.77 out of 5 average rating, 26 reviews3 months ago

We had a nice weekend at Vladimir’s house. I had a small issue getting the lock to open and Vladimir was very responsive and at the door in 3 minutes. The apartment is close to Warren street where all the main shops and restaurants are located. The apartment was perfect for me and my two children.

Apartment in Hudson

What guests are saying

The Enchanted Cottage: An Artist's Retreat.

4.98 out of 5 average rating, 44 reviews2 months ago

Nice, cozy place. Bedroom lamps are unique and nice for setting a relaxing mood. Gwen is a great host, and she made sure we felt taken care of during our stay. The only ding I can give is that the road is somewhat busy for a neighborhood road. There are moments when it is quiet, but also moments when vehicles are three-deep at the nearby intersection.

Cottage in Rhinebeck

What guests are saying

"The Deck Views Were Breathtaking!"

4.96 out of 5 average rating, 48 reviews2 months ago

We had a wonderful stay. The home was perfect for our family ski vacation. We had plenty of space and the views out the back deck were breathtaking. The kitchen had absolutely everything we needed- even pizza pans that we had forgot to bring! The location was ideal for skiing. Less than 5 minutes and we were at the mountain. Lastly, it snowed a bit while we were there and we were impressed to see the driveway was plowed first thing in the morning. Overall, it was a great stay in a wonderful home.

Home in Hillsdale

What guests are saying

Rhinebeck Village Apartment

4.76 out of 5 average rating, 206 reviews1 month ago

Vicky’s charming Airbnb is a perfect getaway! The space is attractively decorated with thoughtful touches that make it feel warm and inviting. The kitchen is impressively well-stocked, making it easy to cook and enjoy meals at home. The bed is super comfy, ensuring a restful night’s sleep. Best of all, the location is ideal—just a short walk to the charming village of Rhinebeck, where you’ll find great shops, restaurants, and cafes. Highly recommend!

Apartment in Rhinebeck

What guests are saying

Lenox, MA Getaway, Mile to town!

4.86 out of 5 average rating, 353 reviews2 months ago

Excellent stay. Chris was really helpful and very responsive to my questions. It was a perfect spot for the family. We enjoyed the board games and open space where we could all hang out. We even saw a bobcat outside the window. Fairly secluded but not far off the beaten path. Very quiet too.

Home in Lenox

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