Title: Hillsdale Guest Houses from CA $151 | 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) # Search Guest Houses in Hillsdale from CA $151 ![](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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Hillsdale Guest Houses ![Exterior](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/1ecb675b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/2567e987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/ca444bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/7c480e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson valley and The Berkshires Cottage Hillsdale 10/10 Exceptional (16) "We had a great weekend stay at The Cottage. We loved the accommodations- great decor! Very clean and comfortable accommodations. Will definitely come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Ann R. CA $108 CA $423 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d28e6aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/c81c0732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites Pittsfield 8.8/10 Excellent (333) "The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candee CA $136 CA $151 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/4e933c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9becd207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (263) "We enjoyed our stay. Excellent location to explore Western Mass!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles D. CA $189 CA $294 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![The Parlor Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b4671c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Parlor Suite | Private kitchen](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b8c74868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/7bbc5c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | In-room dining](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/w5552h4162x0y0-c20c0fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 9 Academy Salisbury 8.6/10 Excellent (7) "The Loft was so beautifully decorated and every detail was perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $664 CA $764 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.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=2025-11-11&endDate=2025-11-12®ionId=183683&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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-Guest-Houses.d183683-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillsdale-Guest-Houses.d183683-aaGuestHouses.Travel-Guide-Accommodation) ## Top Hillsdale Hotel Reviews ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent all the way around" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything is clean " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](//images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg) ### Holiday Inn Express Hotel & Suites West Coxsackie by IHG 10/10 Excellent "Perfect spot for an overnight stay when coming to the area" [](https://expedia.ca/Albany-Hotels-Holiday-Inn-Express-Hotel-Suites-West-Coxsackie.h2591583.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great place. Friendly staff and very well located. Great breakfast options. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean and convenient. Great front desk help. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Had a lovely stay at the Berkshires Untold! We checked in late and the staff reached out to confirm our arrival time and accommodated us without issue. The lobby was absolutely gorgeous and this renovated motel was very well done. We didn’t get to enjoy the fire pits outside but they looked cozy. We also did not have any food or beverage. The room was perfect for two of us, had all the basic amenities and was charming. Overall had a very pleasant stay! " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much traffic noise kept me up until late at night, next time I will request a room facing inward. Not enough staff at the bar and dining during peak weekends, took forever just to get a cup of hot chocolate for the kids. But, very quaint, beautiful, that Main Street is just classic. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Find out more about Hillsdale ## Hillsdale Guest Houses information | Number of reviews | 613 | | --- | --- | | Accommodation | 14 Guest Houses | | Lowest Price | CA $151 | | Highest Price | CA $764 | ## 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) - [Chalets in Ancram](https://www.expedia.ca/Ancram-Chalets.d3000421975-aaChalets.Travel-Guide-Accommodation) - [Holiday Park Resorts in Ancram](https://www.expedia.ca/Ancram-Holiday-Parks.d3000421975-aaHolidayParks.Travel-Guide-Accommodation) - [Cheap Hotels in Ancram](https://www.expedia.ca/Ancram-Hotels-Cheap-Hotels.0-0-d3000421975-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[West Copake Hotels](https://www.expedia.ca/West-Copake-Hotels.d553248635975871453.Travel-Guide-Hotels) - [Flights to Hudson](https://www.expedia.ca/Cheap-Flights-To-Hudson.d55762.Travel-Guide-Flights) - [Flights from Claverack](https://www.expedia.ca/lp/flights/181398/flights-from-claverack) - [Flights from Ancramdale](https://www.expedia.ca/lp/flights/3000421986/flights-from-ancramdale) - [Flights from Augusta (AGS) to Hudson (HCC)](https://www.expedia.ca/lp/flights/ags/hcc/augusta-to-hudson) - [Flights from Bangor (BGR) to Hudson (HCC)](https://www.expedia.ca/lp/flights/bgr/hcc/bangor-to-hudson) - [Flights from Cleveland (CLE) to Hudson (HCC)](https://www.expedia.ca/lp/flights/cle/hcc/cleveland-to-hudson) - [Flights from Cancun (CUN) to Hudson (HCC)](https://www.expedia.ca/lp/flights/cun/hcc/cancun-to-hudson) - [Flights from Milwaukee (MKE) to Hudson (HCC)](https://www.expedia.ca/lp/flights/mke/hcc/milwaukee-to-hudson) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Hornets Nest Paintball](https://www.expedia.ca/Hornets-Nest-Paintball-Ancramdale.d553248621532664789.Vacation-Attraction) - [Visit Hudson](https://www.expedia.ca/Hudson.dx55762) - [Visit Lorenz Park](https://www.expedia.ca/Lorenz-Park.dx553248634999113008) - [Visit Stottville](https://www.expedia.ca/Stottville.dx3000351293) - [Visit Town of Copake](https://www.expedia.ca/Town-Of-Copake.dx553248635976002415) - [Car rental Chatham](https://www.expedia.ca/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide) - [Hawk Rental Cars in Ancram](https://www.expedia.ca/Hawk-Car-Rentals-In-Ancram.d3000421975-c1076.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Chatham](https://www.expedia.ca/Hertz-Car-Rentals-In-Chatham.d6046736-c40.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Claverack](https://www.expedia.ca/Hertz-Car-Rentals-In-Claverack.d181398-c40.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Ancram](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Ancram.d3000421975-c33.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Hudson](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Hudson.d55762-c33.Car-Rental-Guide-Suppliers) - [U-Save Rental Cars in Ancram](https://www.expedia.ca/U-Save-Car-Rentals-In-Ancram.d3000421975-c34.Car-Rental-Guide-Suppliers) - [Chatham Vacation Rentals](https://www.expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals) - [Hudson Vacation Rentals](https://www.expedia.ca/Hudson-Vacation-Rentals.d55762.Travel-Guide-VacationRentals) - [Things to do in Hudson](https://www.expedia.ca/Things-To-Do-In-Hudson.d55762.Travel-Guide-Activities) - [Book Guest Houses in Hillsdale on Expedia.com](https://www.expedia.com/Hillsdale-Guest-Houses.d183683-aaGuestHouses.Travel-Guide-Accommodation)