Last-minute stays near The Berkshires, MA
473 places with check-ins between 2026-10-27 and 2026-11-09, priced from $61 to $710 a night. These are live prices from the last sweep, not a curated list — they move, and some sell out.
- Chic woodland retreat with a soaking tub$163/night$652 totalAirbnb
- Chic woodland retreat with a soaking tub$163/night$652 totalAirbnb
- Mid-century motel 2 miles from skiing$94/night$376 totalAirbnb
- Chic woodland retreat with a soaking tub$179/night$537 totalAirbnb
- Chic woodland retreat with a soaking tub$179/night$537 totalAirbnb
- Chic woodland retreat with a soaking tub$179/night$537 totalAirbnb
- Chic woodland retreat with a soaking tub$179/night$537 totalAirbnb
- Chic woodland retreat with a soaking tub$211/night$422 totalAirbnb
- Mid-century modern, walkable to restaurants$78/night$156 totalAirbnb
- Renovated barn on a working homestead$124/night$496 totalAirbnb
- Renovated barn on a working homestead$132/night$397 totalAirbnb
- Mid-century motel 2 miles from skiing$82/night$165 totalAirbnb
- Renovated barn on a working homestead$132/night$397 totalAirbnb
- Renovated barn on a working homestead$149/night$298 totalAirbnb
- Renovated barn on a working homestead$149/night$298 totalAirbnb
- Mid-century motel 2 miles from skiing$101/night$405 totalAirbnb
- Mid-century motel 2 miles from skiing$119/night$356 totalAirbnb
- Renovated barn on a working homestead$149/night$298 totalAirbnb
- Renovated Victorian in a Berkshires mill town$176/night$353 totalAirbnb
- Renovated Victorian in a Berkshires mill town$170/night$511 totalAirbnb
- Renovated Victorian in a Berkshires mill town$182/night$364 totalAirbnb
- Renovated Victorian in a Berkshires mill town$206/night$824 totalAirbnb
- Private log cabin with forest views$272/night$1,089 totalAirbnb
- Boutique inn 3 minutes from Tanglewood$80/night$161 totalAirbnb
- Mid-century modern, 2 miles from skiing$68/night$204 totalAirbnb
- Mid-century motel 2 miles from skiing$61/night$243 totalAirbnb
- Mid-century modern, 2 miles from skiing$67/night$269 totalAirbnb
- Mid-century modern, walkable to restaurants$74/night$223 totalAirbnb
- Mid-century motel 2 miles from skiing$62/night$187 totalAirbnb
- Mid-century modern, walkable to restaurants$103/night$206 totalAirbnb
- Mid-century motel 2 miles from skiing$65/night$194 totalAirbnb
- Mid-century modern, 2 miles from skiing$71/night$212 totalAirbnb
- Mid-century modern, 2 miles from skiing$70/night$279 totalAirbnb
- Modern studio with treetop views, near Tanglewood$168/night$505 totalAirbnb
- Boutique inn 3 minutes from Tanglewood$100/night$200 totalAirbnb
- Mid-century modern, 2 miles from skiing$82/night$328 totalAirbnb
- Mid-century motel 2 miles from skiing$81/night$325 totalAirbnb
- Mid-century modern, walkable to restaurants$94/night$189 totalAirbnb
- Modern studio with treetop views, near Tanglewood$179/night$358 totalAirbnb
- Modern studio with treetop views, near Tanglewood$179/night$358 totalAirbnb
See all 473 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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