Last-minute stays near The Berkshires, MA

187 places with check-ins between 2026-09-12 and 2026-09-26, priced from $80 to $492 a night. These are live prices from the last sweep, not a curated list — they move, and some sell out.

• King Bed|2m Ski Resort|Stylish|Fast Wi-Fi1 bed · 3 nights · from 2026-09-16$115/night$345 totalAirbnb
• King Bed, Wi-Fi, 2m Ski Resort1 bed · 2 nights · from 2026-09-13$94/night$189 totalAirbnb
• Lovely house in the Berkshires4 beds · 3 nights · from 2026-09-13$260/night$779 totalAirbnb
• Fenced yard, playroom & the Berkshires - $0 fees5 beds · 2 nights · from 2026-09-13$182/night$363 totalAirbnb
• Cozy 2-bedroom apartment with WiFi, fitness room3 beds · 3 nights · from 2026-09-22$151/night$452 totalAirbnb
• King Bed|2m Ski Resort|Stylish|Fast Wi-Fi1 bed · 3 nights · from 2026-09-20$89/night$268 totalAirbnb
• Scribe's Stable | A/C • Screened Porch • Sleeps 64 beds · 2 nights · from 2026-09-13$242/night$485 totalAirbnb
• Misty Pines Cabin | Wood Stove • Sauna6 beds · 2 nights · from 2026-09-12$298/night$596 totalAirbnb
• Lovely house in the Berkshires4 beds · 4 nights · from 2026-09-20$266/night$1,065 totalAirbnb
• Misty Pines Cabin | Wood Stove • Sauna6 beds · 3 nights · from 2026-09-12$261/night$784 totalAirbnb
• Berkshires Barn Stay on Working Homestead3 beds · 3 nights · from 2026-09-22$158/night$474 totalAirbnb
• Berkshires Barn Stay on Working Homestead3 beds · 4 nights · from 2026-09-21$156/night$626 totalAirbnb
• Berkshires Barn Stay on Working Homestead3 beds · 3 nights · from 2026-09-21$159/night$477 totalAirbnb
• Berkshires Barn Stay on Working Homestead3 beds · 4 nights · from 2026-09-20$157/night$629 totalAirbnb
• Scribe's Stable | A/C • Screened Porch • Sleeps 64 beds · 2 nights · from 2026-09-12$237/night$474 totalAirbnb
• Berkshires Barn Stay on Working Homestead3 beds · 2 nights · from 2026-09-22$162/night$325 totalAirbnb
• Cozy 2-bedroom apartment with WiFi, fitness room3 beds · 2 nights · from 2026-09-20$151/night$302 totalAirbnb
• Scribe's Stable | A/C • Screened Porch • Sleeps 64 beds · 4 nights · from 2026-09-12$193/night$772 totalAirbnb
• Lovely house in the Berkshires4 beds · 4 nights · from 2026-09-21$266/night$1,065 totalAirbnb
• King Bed|2m Ski Resort|Stylish|Fast Wi-Fi1 bed · 4 nights · from 2026-09-16$142/night$570 totalAirbnb
• King Bed | Patio | 2m to Ski Resort1 bed · 2 nights · from 2026-09-22$134/night$267 totalAirbnb
• Luxury Berkshires Cottage | Granite Ledge3 beds · 2 nights · from 2026-09-13$392/night$783 totalAirbnb
• Exceptional Stockbridge Retreat4 beds · 4 nights · from 2026-09-13$279/night$1,115 totalAirbnb
• The Serendipity Spot1 bed · 2 nights · from 2026-09-13$218/night$435 totalAirbnb
• Exceptional Stockbridge Retreat4 beds · 4 nights · from 2026-09-20$279/night$1,115 totalAirbnb
• Exceptional Stockbridge Retreat4 beds · 4 nights · from 2026-09-21$279/night$1,115 totalAirbnb
• Charming Handcrafted Cottage in the Berkshires!5 beds · 4 nights · from 2026-09-12$264/night$1,057 totalAirbnb
• Fenced yard, playroom & the Berkshires - $0 fees5 beds · 2 nights · from 2026-09-26$300/night$600 totalAirbnb
• Charming Handcrafted Cottage in the Berkshires!5 beds · 4 nights · from 2026-09-16$266/night$1,063 totalAirbnb
• The Serendipity Spot1 bed · 2 nights · from 2026-09-20$218/night$435 totalAirbnb
• Prime Berkshires Studio|WiFi|Sleeps 4|Pet-friendly2 beds · 2 nights · from 2026-09-12$200/night$401 totalAirbnb
• Downtown Housatonic house –10 miles to Tangelwood4 beds · 2 nights · from 2026-09-20$285/night$570 totalAirbnb
• King Bed|Wi-Fi|2m Ski Resort|Studio1 bed · 3 nights · from 2026-09-13$88/night$263 totalAirbnb
• Quiet refuge in Great Barrington1 bed · 2 nights · from 2026-09-22$80/night$160 totalAirbnb
• Romantic King Room in Downtown Victorian1 bed · 2 nights · from 2026-09-12$87/night$174 totalAirbnb
• Downtown Housatonic house –10 miles to Tangelwood4 beds · 4 nights · from 2026-09-20$268/night$1,071 totalAirbnb
• King Bed|2m Ski Resort|Stylish|Fast Wi-Fi1 bed · 3 nights · from 2026-09-21$87/night$262 totalAirbnb
• King Bed|2m Ski Resort|Stylish|Fast Wi-Fi1 bed · 3 nights · from 2026-09-22$89/night$267 totalAirbnb
• Sweet Victorian in Housatonic4 beds · 4 nights · from 2026-09-13$191/night$765 totalAirbnb
• Fenced yard, playroom & the Berkshires - $0 fees5 beds · 4 nights · from 2026-09-13$194/night$777 totalAirbnb

See all 187 The Berkshires, MA deals, filtered and sorted →

How these are picked

Every price here was recorded against that property's own recent history and against the market, so “cheap” means cheap for this place at this time — not a discount off a number someone made up. Nothing on this page is a paid placement.

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