Last-minute stays near Bear Mountain & Hudson Highlands, NY

309 places with check-ins between 2026-09-12 and 2026-09-26, priced from $90 to $606 a night. These are live prices from the last sweep, not a curated list — they move, and some sell out.

• Architect's Hudson Valley Home in the Woods2 beds · 3 nights · from 2026-09-13$194/night$583 totalAirbnb
• Mod Scandinavian! Tiny Flower Farm2 beds · 2 nights · from 2026-09-13$119/night$238 totalAirbnb
• The Woodland Valley Spa Cabin (20min to Woodstock)2 beds · 4 nights · from 2026-09-13$199/night$796 totalAirbnb
• Pet-Friendly 3BR Retreat – Walk to Shops & Cafe3 beds · 2 nights · from 2026-09-20$315/night$630 totalAirbnb
• Mindful Escape: Theater, Trails, Wood Stove2 beds · 3 nights · from 2026-09-15$155/night$466 totalAirbnb
• Architect's Hudson Valley Home in the Woods2 beds · 2 nights · from 2026-09-13$248/night$497 totalAirbnb
• Sunset Bungalow-Mt views on 130acre forest & falls2 beds · 2 nights · from 2026-09-13$184/night$368 totalAirbnb
• Cabin in the heart of the Hudson Valley, Cabin 31 bed · 2 nights · from 2026-09-17$166/night$331 totalAirbnb
• Walkable Studio with a Fire Pit1 bed · 4 nights · from 2026-09-21$120/night$478 totalAirbnb
• Walkable Studio with a Fire Pit1 bed · 3 nights · from 2026-09-22$128/night$383 totalAirbnb
• Walkable Studio with a Fire Pit1 bed · 3 nights · from 2026-09-21$128/night$383 totalAirbnb
• Walkable Studio with a Fire Pit1 bed · 2 nights · from 2026-09-21$144/night$288 totalAirbnb
• Walkable Studio with a Fire Pit1 bed · 2 nights · from 2026-09-23$144/night$288 totalAirbnb
• Walkable Studio with a Fire Pit1 bed · 2 nights · from 2026-09-22$144/night$288 totalAirbnb
• Spacious Parlor Apartment w/ Hudson River Views2 beds · 3 nights · from 2026-09-13$151/night$452 totalAirbnb
• Spacious Parlor Apartment w/ Hudson River Views2 beds · 2 nights · from 2026-09-13$150/night$300 totalAirbnb
• Be in Nature at this Gorgeous Riverfront Cabin6 beds · 2 nights · from 2026-09-23$278/night$555 totalAirbnb
• Cozy Autumn Cold Spring Getaway1 bed · 3 nights · from 2026-09-17$207/night$622 totalAirbnb
• Glamper Royal1 bed · 4 nights · from 2026-09-15$191/night$763 totalAirbnb
• Glamper Royal1 bed · 3 nights · from 2026-09-16$203/night$610 totalAirbnb
• Glamper Royal1 bed · 2 nights · from 2026-09-17$228/night$457 totalAirbnb
• Spacious Parlor Apartment w/ Hudson River Views2 beds · 4 nights · from 2026-09-13$166/night$663 totalAirbnb
• Cozy Autumn Cold Spring Getaway1 bed · 3 nights · from 2026-09-18$226/night$678 totalAirbnb
• Enchanted Woodland Tiny Home Retreat1 bed · 2 nights · from 2026-09-23$172/night$343 totalAirbnb
• Glamper Royal1 bed · 4 nights · from 2026-09-13$203/night$813 totalAirbnb
• Cozy Autumn Cold Spring Getaway1 bed · 4 nights · from 2026-09-17$196/night$784 totalAirbnb
• Hudson Valley's own Walden Pond5 beds · 3 nights · from 2026-09-16$142/night$426 totalAirbnb
• Glamper Royal1 bed · 3 nights · from 2026-09-13$220/night$660 totalAirbnb
• Hudson Valley's own Walden Pond5 beds · 4 nights · from 2026-09-15$132/night$528 totalAirbnb
• Hudson Valley's own Walden Pond5 beds · 4 nights · from 2026-09-26$132/night$528 totalAirbnb
• Quiet 1BR+ Riverview Retreat2 beds · 4 nights · from 2026-09-21$202/night$808 totalAirbnb
• Climb, bike and relax at Escape to the gunks!2 beds · 2 nights · from 2026-09-12$175/night$350 totalAirbnb
• Country Getaway - Close to Hiking & Storm King2 beds · 2 nights · from 2026-09-15$95/night$190 totalAirbnb
• Cozy Autumn Cold Spring Getaway1 bed · 4 nights · from 2026-09-18$209/night$835 totalAirbnb
• Architectural Private Gem w/ Views + Hot Tub4 beds · 2 nights · from 2026-09-12$606/night$1,212 totalAirbnb
• Architectural Private Gem w/ Views + Hot Tub4 beds · 3 nights · from 2026-09-12$547/night$1,640 totalAirbnb
• Quiet 1BR+ Riverview Retreat2 beds · 3 nights · from 2026-09-21$211/night$632 totalAirbnb
• Architectural Private Gem w/ Views + Hot Tub4 beds · 4 nights · from 2026-09-12$517/night$2,068 totalAirbnb
• Charming Apartment in Newburgh2 beds · 4 nights · from 2026-09-13$117/night$468 totalAirbnb
• Charming Apartment in Newburgh2 beds · 3 nights · from 2026-09-13$126/night$377 totalAirbnb

See all 309 Bear Mountain & Hudson Highlands, NY 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.

This site is supported by advertising and affiliate links. If you book through an affiliate link we may earn a commission at no extra cost to you. Neither ever affects which stays we show or how they are ranked.