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Kid-friendly vacation rentals in Berkshire County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Berkshire County

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

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Cabin in Stephentown

4.86 out of 5 average rating, 268 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Chalet in Otis

4.95 out of 5 average rating, 382 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

Rental unit in Copake Falls

4.92 out of 5 average rating, 300 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Guesthouse in North Adams

5 out of 5 average rating, 241 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Treehouse in Tyringham

5 out of 5 average rating, 269 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Home in Stockbridge

4.95 out of 5 average rating, 110 reviews

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Rental unit in Canaan

4.99 out of 5 average rating, 147 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Home in Becket

4.87 out of 5 average rating, 324 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Farm stay in Pittsfield

4.99 out of 5 average rating, 173 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guesthouse in Lenox

4.94 out of 5 average rating, 341 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Home in Great Barrington

4.97 out of 5 average rating, 241 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Rental unit in Great Barrington

4.95 out of 5 average rating, 353 reviews

Private En Suite in Beautiful Victorian

The room is light and airy with morning sun and the shade of the large front porch in the afternoon. This is a place to enjoy a meal or just lounge and relax with a view of the gardens and surrounding woods. This space features a private entrance, a kitchenette and full bathroom and very comfortable queen bed. In mid July 2024 we added air conditioning.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Berkshire County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Becket

4.93 out of 5 average rating, 109 reviews

Beautiful, quiet and cozy home in Becket!

Home in Dalton

4.99 out of 5 average rating, 140 reviews

Cleveland House - renovated Berkshires' gem.

Home in Stockbridge

4.97 out of 5 average rating, 104 reviews

Greek Revival Farmhouse

Home in Lee

4.9 out of 5 average rating, 228 reviews

1817 Berkshire Farmhouse- Close to Everything.

Home in Monterey

4.92 out of 5 average rating, 131 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

Home in Cheshire

4.86 out of 5 average rating, 212 reviews

19th c. Barn in The Berkshires

Home in Dalton

4.93 out of 5 average rating, 184 reviews

Brooksong, the perfect Berkshires getaway

Home in Chester

4.96 out of 5 average rating, 337 reviews

Riverfront Getaway

Kid-friendly apartment rentals

Rental unit in Adams

4.85 out of 5 average rating, 132 reviews

full apartment in adams self check in

Rental unit in Lenox

4.88 out of 5 average rating, 187 reviews

Station House 1E Private Room & Bath

Rental unit in Lenox Dale

4.91 out of 5 average rating, 127 reviews

Charming 2BD apartment.

Rental unit in Great Barrington

5 out of 5 average rating, 111 reviews

Walk Everywhere! | Relax in Easy Elegance!

Rental unit in North Adams

4.98 out of 5 average rating, 190 reviews

Overlooking the city in a quiet 7 unit building.

Rental unit in Lanesborough

4.87 out of 5 average rating, 108 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

Rental unit in Williamstown

4.93 out of 5 average rating, 282 reviews

COLD SPRING

Rental unit in Great Barrington

4.93 out of 5 average rating, 190 reviews

Secluded but not isolated Berkshire Retreat

Kid-friendly condo rentals

Condo in Hancock

5 out of 5 average rating, 6 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

Condo in Hancock

4.98 out of 5 average rating, 42 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Condo in Lenox

5 out of 5 average rating, 30 reviews

Spacious 3 bedroom apt in Lenox historic downtown

Condo in North Adams

4.95 out of 5 average rating, 62 reviews

Newly renovated 2BR on historic Eagle Street.

Condo in North Adams

4.9 out of 5 average rating, 10 reviews

Charming downtown Condo!

Condo in Hancock

4.91 out of 5 average rating, 54 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Condo in Hancock

4.85 out of 5 average rating, 142 reviews

Cozy Condo @ Jiminy Peak

Destinations to explore