Condo vacation rentals in The Berkshires
Find and book unique condos on Airbnb
Top-rated condo rentals in The Berkshires
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 The Berkshires condo rentals
Weekly condo rentals
Condo in Stratton
4.94 out of 5 average rating, 138 reviewsUpdated Ski in/Ski out Stratton Condo!
Oct 12 – 19
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 15 – 22
Condo in Saratoga Springs
4.97 out of 5 average rating, 100 reviewsUltimate Location The Belmont, Track, Broadway
Aug 26 – Sep 2
Condo in Hunter
4.87 out of 5 average rating, 254 reviewsMountainside Haven - walk to Hunter Mtn!
Sep 30 – Oct 7
Condo in Windham
4.84 out of 5 average rating, 112 reviewsStudio 3 BEDS-SLEEP 4
Jan 25 – Feb 1
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Oct 1 – 8
Condo in Stratton
4.88 out of 5 average rating, 107 reviewsPerfect Location! Steps to Village and Mountain
Sep 16 – 23
Condo in Hunter
4.96 out of 5 average rating, 227 reviewsMint*Cozy Ski On/Off Hunter Mt Condo w/Fireplace
Jun 21 – 28
Pet-friendly condo rentals
Condo in Hunter
4.8 out of 5 average rating, 283 reviewsMountain side ski and snowboard condo
Jan 12 – 19
Condo in Kingston
4.91 out of 5 average rating, 105 reviewsCozy home walking distance to cafés & waterfront
Sep 8 – 15
Condo in Dover
4.84 out of 5 average rating, 157 reviewsMount Snow Close, Great Price, Lots of Room
Sep 23 – 30
Condo in West Kill
4.85 out of 5 average rating, 131 reviewsTrailside At Hunter-Phase II-Hunter NY
Oct 25 – Nov 1
Condo in Hartford
5.0 out of 5 average rating, 37 reviewsPosh Pad in The Business District
Aug 21 – 28
Condo in North Adams
5.0 out of 5 average rating, 23 reviewsNewly renovated 2BR on historic Eagle Street.
Aug 9 – 16
Condo in Albany
4.89 out of 5 average rating, 45 reviewsCozy luxury brownstone w/ parking & yard
Apr 20 – 27
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Jul 29 – Aug 5
Condo rentals with a pool
Condo in Windham
4.74 out of 5 average rating, 243 reviewsSummer getaway w/Pool & Tennis Court
Aug 16 – 23
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Feb 9 – 16
Condo in New Britain
4.85 out of 5 average rating, 40 reviewsBeautiful Space All For You!
Sep 18 – 25
Condo in Dover
4.94 out of 5 average rating, 53 reviewsMt. Snow Dream Mtn View+Fireplace!
Aug 27 – Sep 3
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
Aug 4 – 11
Condo in Dover
5.0 out of 5 average rating, 36 reviewsFour Seasons Slope-side Getaway at Mount Snow
Jul 18 – 25
Condo in Hancock
4.95 out of 5 average rating, 22 reviewsJiminy Peak Apartment
May 22 – 29
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
May 12 – 19
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