Title: Hillsdale Cottages from CA $250 | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hillsdale Cottage Rentals from CA $250 ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Hillsdale Cottages ![Exterior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/0607b999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/9cd00997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/737a2fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/f395be91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cottage with beautiful views and easy access to Catskills activities. Saugerties 10/10 Exceptional (12) "Great spot!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dylan CA $139 CA $250 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Saugerties-Hotels-The-Country-Cottage.h99543833.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/6d8828e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/6f07f40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/fad53257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/f47ba498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming loft cottage in tranquil Germantown with WiFi, AC Germantown 10/10 Exceptional (4) "Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter S. CA $153 CA $297 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Germantown-Hotels-Charming-Loft-Cottage-In-Tranquil-Germantown-With-WiFi.h113393517.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/d43e2385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/6c73b5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/e22c1aaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/b2de5a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Peace in this Beautiful country cottage nestled beneath the mountains Catskill 9.8/10 Exceptional (8) "Nice house, well stocked and nice outdoor area/deck." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet B. CA $209 CA $468 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/a0bb237f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/7a00417e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/9bb4254b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/b25675ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly Hudson Escape w/ Hot Tub Stottville CA $189 CA $423 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Hudson-Hotels-Pet-Friendly-Hudson-Escape-W-Hot-Tub.h120658954.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69550000/69545600/69545543/a308218e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/70000000/69550000/69545600/69545543/9ac4e7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69550000/69545600/69545543/a6989dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/70000000/69550000/69545600/69545543/bd7ad5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hits Adjacent | Pet Friendly | Caraway Cottage Saugerties 10/10 Exceptional (13) "We enjoyed our stay, nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beverly L. CA $336 CA $664 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Saugerties-Hotels-Hits-Adjacent-Pet-Friendly-Caraway-Cottage.h69545543.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/052d8e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/ed51271f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/70f669a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/be2467fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Blue Elm - A Historic Berkshire Cottage Sheffield 10/10 Exceptional (11) "Everything was great...and beautiful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole L. CA $280 CA $567 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Sheffield-Hotels-The-Blue-Elm-A-Historic-Berkshire-Cottage.h101469345.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/0791e99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/2cd54c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![15 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/ca2ed981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/df08517c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires farm, 30+ guests, 50 acres New Lebanon CA $1,360 CA $2,387 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/New-Lebanon-Hotels-Berkshires-Farm.h99407400.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=2025-11-03&endDate=2025-11-04®ionId=183683&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d183683-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillsdale-Cottages.d183683-aaCottages.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 "Kitchen and parking both very good" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "In a very nice annex suite." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Nice clean and new. I had a nice stay, with restaurants across the street and a dunkin very close for the morning " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Good " [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.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 "Enjoyable stay. Staff were very nice. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![St. Charles Hotel](//images.trvl-media.com/lodging/2000000/1640000/1639400/1639318/d1c362b4_y.jpg) ### St. Charles Hotel 10/10 Excellent "Rooms clean minimal and comfortable bed" [](https://expedia.ca/Hudson-Hotels-St-Charles-Hotel.h1639318.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Yes" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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 stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try to come down twice a month from CNY--needless to say it is expensive for me.. Random question-- do you offer discounts?" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Clean room, nice view" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Hillsdale ## Hillsdale Cottages information | Number of reviews | 44 | | --- | --- | | Accommodation | 156 Cottages | | Lowest Price | CA $250 | | Highest Price | CA $2,387 | ## Frequently asked questions ### Why book your cottage in Hillsdale with Expedia? > We think that vacations should be easy, so if you're looking for cottages in Hillsdale at an affordable rate, Expedia has got your back. Keep the budget under control and check in to an inexpensive option far away from the city rush, or splurge on a 5-star cottage to treat your loved ones. ### How can I find cheap cottages in Hillsdale? > The quickest way to score cheap cottages in Hillsdale is with Expedia's user-friendly filter tool. Refine your search results by star rating, budget and amenities to take advantage of awesome rates with only a few clicks. ### What is there to do in Hillsdale near my cottage? > The ideal travel accessory is a well-thought-out travel plan. [Catamount Aerial Adventure Park](https://www.expedia.ca/Catamount-Aerial-Adventure-Park-Hillsdale.d553248621532664791.Vacation-Attraction) is a wonderful spot to kick off your exploration of Hillsdale. ## 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) - [Luxury Hotels in Ancram](https://www.expedia.ca/Ancram-Hotels-Luxury-Hotel.0-0-d3000421975-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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[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 Cottages in Hillsdale on Expedia.com](https://www.expedia.com/Hillsdale-Cottages.d183683-aaCottages.Travel-Guide-Accommodation)