Title: Cheshire Guest Houses from CA $165 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.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 Next weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire guest houses ![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/fdc80b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/7d4b7b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blooming Inn [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) Shelburne Falls 9.2/10 Wonderful (130 reviews) "Beautiful comfortable home with many thoughtful touches" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $127 CA $208 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/4092a889.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/2000000/1460000/1457800/1457797/0e28a2e6.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/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (355 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $148 CA $165 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![55-inch LCD TV with digital channels, printers](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/0a4a8480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/20208a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed (Room 4)](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/219287f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/f9501b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revival House [](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information) Adams 9.0/10 Wonderful (26 reviews) "Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) melissa CA $203 CA $227 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/321c91e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/2acfd77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/1d55e99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/9db8fbec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In town, newly remodeled studio with private balcony [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) Shelburne Falls 10/10 Exceptional (119 reviews) "set up great! very clean great location, WONDERFUL" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laurie p. CA $116 CA $198 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/0ab1624d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Berkshire Village Carriage House - Super Private!! [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) Lanesborough 9.8/10 Exceptional (273 reviews) "It was a cute property- just what we needed. Nice location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda M. CA $183 CA $283 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.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=2026-02-26&endDate=2026-02-27®ionId=6005398&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6005398) ![](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%2FCheshire-Guest-Houses.d6005398-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Guest-Houses.d6005398-aaGuestHouses.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "Clean room, nice staff , decent breakfast. Overall a good stay . " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Clean room, friendly staff, and a delicious breakfast. The sauna was a wonderful surprise on a frigid day. We were grateful to find an EV charger at the inn. (They could use a couple more of them!)" [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and will definitely look to return to this property in the future. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Spacious 2 bed 2 bath!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "loved " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ## Find out more about Cheshire ## Cheshire Guest Houses information | Number of reviews | 902 | | ----------------- | -------------- | | Accommodation | 9 Guest Houses | | Lowest Price | CA $165 | | Highest Price | CA $283 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in North Adams ](https://www.expedia.ca/4Star-North-Adams-Hotels.s40-0-d9137.Travel-Guide-Filter-Hotels) - [Farmstay in Adams ](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams ](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams ](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams ](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - 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