Condo vacation rentals in Berkshire County
Find and book unique condos on Airbnb
Top-rated condo rentals in Berkshire County
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County condo rentals
Weekly condo rentals
Room in Great Barrington
4.96 out of 5 average rating, 150 reviewsQuiet refuge in Great Barrington
Dec 11 – 18
Room in Lenox
Tranquil Church Apt Lenox MA - 1 BD
Oct 12 – 19
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
May 9 – 16
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 23 – 30
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 4 – 11
Condo in North Adams
5.0 out of 5 average rating, 22 reviewsNewly renovated 2BR on historic Eagle Street.
Aug 29 – Sep 5
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Jul 27 – Aug 3
Condo rentals with a pool
Condo in Hancock
4.8 out of 5 average rating, 5 reviewsSki-in/Ski-Out on Jiminy Peak
Nov 26 – Dec 3
Condo in Hancock
Condo Resort at Jiminy Peak Ski Mountain's Base
Dec 29 – Jan 5
Condo in Williamstown
Escape to Serenity: Unplug in the Berkshires!
Dec 20 – 27
Condo in Williamstown
Vacation Village in the Berkshires Resort Suite B
Apr 1 – 8
Condo in Hancock
Ski in & Ski out Deluxe Condo
Nov 2 – 9
Condo in Hancock
4.93 out of 5 average rating, 58 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
Jan 25 – Feb 1
Condo in Hancock
4.95 out of 5 average rating, 22 reviewsJiminy Peak Apartment
Jan 14 – 21
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
Sep 10 – 17
Private condo rentals
Condo in North Adams
New place to stayDowntown Condo - walk to MoCA
Apr 13 – 20
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
May 9 – 16
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 23 – 30
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 4 – 11
Condo in North Adams
5.0 out of 5 average rating, 22 reviewsNewly renovated 2BR on historic Eagle Street.
Aug 29 – Sep 5
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Jul 27 – Aug 3
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
May 10 – 17
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