Title: Hillsdale Vacation Home Rentals from CA $215: Search Top Private Vacation Homes for Rent | Expedia.ca [Hillsdale Travel Guide](https://expedia.ca/Hillsdale.dx183683)[Hotels in Hillsdale](https://expedia.ca/Hillsdale-Hotels.d183683.Travel-Guide-Hotels)[Vacation Rentals in Hillsdale](https://expedia.ca/Hillsdale-Vacation-Rentals.d183683.Travel-Guide-VacationRentals)[Hillsdale Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsdale.d183683.Car-Rental-Guide)[Hillsdale Vacation Packages](https://expedia.ca/Hillsdale.d183683.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillsdale vacation homes ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/23a17279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Berkshires Home Near Tanglewood, Trails & Wineries [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) Lebanon Springs 9.0/10 Wonderful (21 reviews) "Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy D. CA $200 CA $533 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) Great Barrington 9.8/10 Exceptional (26 reviews) "Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron M. CA $203 CA $345 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-950a0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All the comforts of home [](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) Hudson 9.2/10 Wonderful (29 reviews) "Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marisa P. CA $164 CA $215 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Tanglewood: Historic Summer Retreat [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) New Lebanon 9.2/10 Wonderful (25 reviews) "Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. CA $167 CA $490 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) Lee 9.4/10 Exceptional (3 reviews) "The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah D. CA $250 CA $640 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Cozy Victorian in Housatonic. Close to everything. [](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information) Housatonic 10/10 Exceptional (3 reviews) "Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl F. CA $188 CA $371 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/9bc69856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/4be6f104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/38d4cb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/6468f916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information) Stephentown 8.0/10 Very good (1 review) "excellent communication with property manager." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy H. CA $244 CA $784 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/0ac6466c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/b90450d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/6a099f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/ecb19306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super Comfortable Water-view Home in Saugerties [](https://www.expedia.ca/Saugerties-Hotels-The-Longview-House-Near-Saugerties-Lighthouse.h83464810.Hotel-Information) Saugerties 9.8/10 Exceptional (6 reviews) "Wonderful home in a very quiet and peaceful neighborhood. Well stocked kitchen, bathrooms etc. immaculately clean! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) denise g. CA $262 CA $885 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Saugerties-Hotels-The-Longview-House-Near-Saugerties-Lighthouse.h83464810.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/d16bb4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c945b9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/0afecb87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/fee8af1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Luxurious Cabin, Catskills - The Tiny Nook [](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information) Catskill 10/10 Exceptional (8 reviews) "Great place. Exactly like the pictures. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert a. CA $223 CA $479 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540561/fe1d7007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540561/e81ffc9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540561/e7dd0555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69540600/69540561/a4748cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New House w gated backyard that is located right at the Saugerties Village [](https://www.expedia.ca/Saugerties-Hotels-Brand-New-House-W-Gated-Backyard-That-Is-Located-Right-At-The-Saugerties-Village.h69540561.Hotel-Information) Saugerties 10/10 Exceptional (38 reviews) "Cute house in a great location. Thanks for the stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole S. CA $263 CA $598 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Saugerties-Hotels-Brand-New-House-W-Gated-Backyard-That-Is-Located-Right-At-The-Saugerties-Village.h69540561.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (7 reviews) "The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz V. CA $374 CA $689 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Ski Getaway in the Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.2/10 Wonderful (7 reviews) "Close to a great bakery and near to a farm market and shopping mall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristine C. CA $266 CA $392 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/dac46480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/18a5d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/97c48259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/c0195267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson Hot Tub & Pet Escape [](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) Stottville CA $207 CA $401 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/fbe651db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/1d777bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/afeec342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/d106f31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill Stay w/ Deck & Fire Pit [](https://www.expedia.ca/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.Hotel-Information) Catskill 8.8/10 Excellent (3 reviews) "we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) raquel p. CA $209 CA $618 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.Hotel-Information) ![TV, video games](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/370d084b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/969f8541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/2518777f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/34e259bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New! The Den on Denniston, with game room, movie theater, fire pit and more. Close To HITS Horse show & Hunter Mountain skiing [](https://www.expedia.ca/Saugerties-Hotels-New-Denniston-Den.h120449785.Hotel-Information) Saugerties CA $184 CA $617 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Saugerties-Hotels-New-Denniston-Den.h120449785.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/b090eb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/ea15296d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/7ecad611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/277bbd12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite 3 - Quiet and private accommodations in a country setting. [](https://www.expedia.ca/Quiet-And-Private-Accommodations-In-A-Country-Setting.h78257590.Hotel-Information) Spencertown 10/10 Exceptional (1 review) "Fantastic place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $296 CA $379 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Quiet-And-Private-Accommodations-In-A-Country-Setting.h78257590.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in beautiful Berkshires, close to amenities! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) Pittsfield CA $303 CA $491 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/77b3a9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/2d6b60e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/c50938c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/a0cefac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson [](https://www.expedia.ca/Hudson-Hotels-Blue-Heron-House-3BR-Creekside-Retreat-With-Hot-Tub.h120277085.Hotel-Information) Hudson 10/10 Exceptional (3 reviews) "Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim W. CA $387 CA $821 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Hudson-Hotels-Blue-Heron-House-3BR-Creekside-Retreat-With-Hot-Tub.h120277085.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/7de1909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/8d649c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/a00a49e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/0b1a642a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot tub on water, 5min HITS, 20mi to Hunter skiing [](https://www.expedia.ca/Malden-Hotels-River-Front-Luxury-Hot-Tub.h116728281.Hotel-Information) Malden 10/10 Exceptional (4 reviews) "It was terrific!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra M. CA $401 CA $1,168 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Malden-Hotels-River-Front-Luxury-Hot-Tub.h116728281.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/28a8e29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/f8964f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/c6469257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/34815278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 Bedroom | Cozy Lounge | Spacious [](https://www.expedia.ca/Catskill-Hotels-1-Bedroom-Cozy-Lounge-Spacious.h123260649.Hotel-Information) Catskill [](https://www.expedia.ca/Catskill-Hotels-1-Bedroom-Cozy-Lounge-Spacious.h123260649.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-01&endDate=2026-02-02®ionId=183683&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=CABIN) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=VILLA) Condos [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Hillsdale%2C+New+York%2C+United+States+of+America®ionId=183683&latLong=42.179245%2C-73.525024&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHillsdale-Private-Vacation-Homes.d183683-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillsdale-Private-Vacation-Homes.d183683-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Hillsdale Hotel Reviews ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Everything was very good. The room was clean and cozy." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Great food, nice room, nice staff. " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "It’s an older property, but clean and comfortable. The staff was extremely friendly and welcoming. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "The stay was wonderful. The beautiful place. All very comfortable!" [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Staff was very courteous and rooms clean." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "everything" [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg) ### Courtyard by Marriott Lenox Berkshires 10/10 Excellent "Our stay was great! " [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG](https://images.trvl-media.com/lodging/35000000/34870000/34864800/34864714/9b72516c_y.jpg) ### Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG 10/10 Excellent "Room very clean " [](https://expedia.ca/Kingston-Hotels-Holiday-Inn-Express-Suites-Saugerties-Hudson-Valley.h34864714.Hotel-Information) ## Find out more about Hillsdale ## Hillsdale Vacation Homes information | Number of reviews | 174 | | ----------------- | ------------------ | | Accommodation | 641 Vacation Homes | | Lowest Price | CA $215 | | Highest Price | CA $1,179 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Aparthotels in Ancram ](https://www.expedia.ca/Ancram-Apart-Hotels.d3000421975-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Ancram ](https://www.expedia.ca/Ancram-Bed-And-Breakfast.d3000421975-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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