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Kid-friendly vacation rentals in Berkshire County

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Top-rated kid-friendly rentals in Berkshire County

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

Guest favorite
Chalet in Otis
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
Sep 7 – 14
$352 per night
4.94 out of 5 average rating, 341 reviews
Guest favorite
Treehouse in Tyringham
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.
Jun 3 – 10
$270 per night
5.0 out of 5 average rating, 216 reviews
Guest favorite
Cottage in Great Barrington
Artist Cottage
Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.
Jun 12 – 19
$181 per night
4.93 out of 5 average rating, 231 reviews

Popular amenities for Berkshire County kid-friendly rentals

Kid-friendly house rentals

Guest favorite
Home in Monterey
Charming cottage w/ gorgeous views.
Jan 27 – Feb 3
$145 per night
4.92 out of 5 average rating, 306 reviews
Guest favorite
Home in Dalton
The Yellow House
Oct 3 – 10
$104 per night
4.91 out of 5 average rating, 111 reviews
Guest favorite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Apr 26 – May 3
$300 per night
4.92 out of 5 average rating, 167 reviews
Guest favorite
Home in Canaan
Country Cottage
Dec 25 – Jan 1
$135 per night
5.0 out of 5 average rating, 129 reviews
Superhost
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
Dec 1 – 8
$210 per night
4.86 out of 5 average rating, 284 reviews
Guest favorite
Home in Cheshire
Ski at 19th c. Barn in The Berkshires
Jan 22 – 29
$338 per night
4.85 out of 5 average rating, 196 reviews
Guest favorite
Home in Chester
Riverfront Getaway
Dec 5 – 12
$159 per night
4.96 out of 5 average rating, 304 reviews
Guest favorite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
Nov 21 – 28
$400 per night
4.99 out of 5 average rating, 118 reviews
Guest favorite
Home in Becket
Lake front retreat - Stylish Berkshire home
Jun 25 – Jul 2
$528 per night
4.93 out of 5 average rating, 114 reviews
Guest favorite
Home in Lee
Cozy Berkshires Cottage
May 22 – 29
$117 per night
4.89 out of 5 average rating, 233 reviews
Guest favorite
Home in New Lebanon
The old sawmill from 1771
Nov 2 – 9
$125 per night
4.99 out of 5 average rating, 347 reviews
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Jun 23 – 30
$225 per night
4.89 out of 5 average rating, 199 reviews

Kid-friendly apartment rentals

Guest favorite
Apartment in Petersburg
The Beer Diviner Brewery Apartment
Jul 23 – 30
$59 per night
4.85 out of 5 average rating, 140 reviews
Guest favorite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
Sep 23 – 30
$96 per night
4.95 out of 5 average rating, 313 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Mar 15 – 22
$60 per night
4.83 out of 5 average rating, 151 reviews
Guest favorite
Apartment in Lenox
Station House 1E Private Room & Bath
May 9 – 16
$64 per night
4.88 out of 5 average rating, 168 reviews
Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
May 30 – Jun 6
$130 per night
4.93 out of 5 average rating, 245 reviews
Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
Mar 28 – Apr 4
$114 per night
4.91 out of 5 average rating, 117 reviews
Guest favorite
Apartment in North Adams
See MoCA from your mansion+Sauna! Ski nearby!
Dec 7 – 14
$135 per night
4.97 out of 5 average rating, 386 reviews
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
Oct 24 – 31
$144 per night
5.0 out of 5 average rating, 317 reviews
Superhost
Apartment in Great Barrington
GB Eclectic Victorian
May 5 – 12
$171 per night
4.95 out of 5 average rating, 131 reviews
Superhost
Apartment in Lee
Cozy Berkshire Cottage Style Apartment
Sep 7 – 14
$100 per night
4.78 out of 5 average rating, 106 reviews
Guest favorite
Apartment in North Adams
River Apartment, walk to MassMOCA and downtown
Jun 18 – 25
$86 per night
4.89 out of 5 average rating, 214 reviews
Guest favorite
Apartment in Lenox
Lovely Downtown Lenox apt, walk to everything!
May 20 – 27
$375 per night
4.95 out of 5 average rating, 105 reviews

Kid-friendly condo rentals

Guest favorite
Condo in Hancock
Cozy Condo @ Jiminy Peak
Aug 9 – 16
$150 per night
4.83 out of 5 average rating, 129 reviews
Superhost
Condo in North Adams
Downtown Flat Iron Condo - walk to MoCA #12
Jul 11 – 18
$98 per night
4.91 out of 5 average rating, 206 reviews
Guest favorite
Condo in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
Oct 2 – 9
$139 per night
4.89 out of 5 average rating, 47 reviews
Guest favorite
Condo in North Adams
Newly renovated 2BR on historic Eagle Street.
May 8 – 15
$137 per night
5.0 out of 5 average rating, 14 reviews
Guest favorite
Condo in Lenox
Spacious 3 bedroom apt in Lenox historic downtown
Sep 30 – Oct 7
$332 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Condo in Hancock
Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Jun 30 – Jul 7
$461 per night
4.97 out of 5 average rating, 34 reviews
Guest favorite
Condo in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
Jun 2 – 9
$235 per night
4.96 out of 5 average rating, 25 reviews
Guest favorite
Condo in Hancock
Upscale 2 bed/2bath Condo at a Mountain Resort!
Apr 9 – 16
$206 per night
4.94 out of 5 average rating, 18 reviews
Guest favorite
Condo in Hancock
Jiminy Peak Apartment
Oct 29 – Nov 5
$160 per night
4.94 out of 5 average rating, 17 reviews
Guest favorite
Condo in Hancock
All-season Berkshires ski resort condo - Sitzmark
May 11 – 18
$151 per night
4.89 out of 5 average rating, 19 reviews
Guest favorite
Condo in Lenox
Heart of Lenox!! - Renovated downtown apartment
Mar 13 – 20
$271 per night
4.89 out of 5 average rating, 73 reviews
Guest favorite
Condo in Hancock
Unique - Country suite @ Jiminy Peak
Apr 29 – May 6
$196 per night
4.91 out of 5 average rating, 32 reviews

Destinations to explore