Title: Chatham Guest Houses from CA $152 | Expedia.ca [Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d6046736.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d6046736.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 Guest Houses in Chatham from CA $152 ![](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=6046736&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chatham Guest Houses ![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) ![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) ![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) ### The Central Downtown Inn & Suites Pittsfield 8.8/10 Excellent (328) "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 $152 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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.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) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (261) "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 $296 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/1ecb675b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/5ec352f5.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) ![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 (15) "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 $114 CA $431 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/7aa060b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Deluxe King](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ed603c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Birchwood Suite](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ded30af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/65e7ad44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dewey Lenox 8.8/10 Excellent (326) "Great spot. Lots of history. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Neil CA $183 CA $205 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-The-Dewey.h5202927.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=6046736&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%2FChatham-Guest-Houses.d6046736-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChatham-Guest-Houses.d6046736-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chatham 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) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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) ### 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) ![Comfort Inn & Suites East Greenbush - Albany](//images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "Quiet" [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.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) ## Find out more about Chatham ## Chatham Guest Houses information | Number of reviews | 793 | | --- | --- | | Accommodation | 11 Guest Houses | | Lowest Price | CA $152 | | Highest Price | CA $431 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cheap Hotels in Austerlitz](https://www.expedia.ca/Austerlitz-Hotels-Cheap-Hotels.0-0-d500771-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Austerlitz](https://www.expedia.ca/Austerlitz-Hotels-Luxury-Hotel.0-0-d500771-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Austerlitz Hotels](https://www.expedia.ca/Austerlitz-Hotels.d500771.Travel-Guide-Hotels) - [Boutique Hotels in Canaan](https://www.expedia.ca/Canaan-Hotels-Boutique-Hotel.0-0-d55619-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Canaan](https://www.expedia.ca/Canaan-Hotels-Cheap-Hotels.0-0-d55619-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Flights to Niverville](https://www.expedia.ca/Cheap-Flights-To-Niverville.d3000449167.Travel-Guide-Flights) - [Flights to Old Chatham](https://www.expedia.ca/Cheap-Flights-To-Old-Chatham.d6190671.Travel-Guide-Flights) - [Flights from Nassau](https://www.expedia.ca/lp/flights/3000449135/flights-from-nassau) - [Flights from Old Chatham](https://www.expedia.ca/lp/flights/6190671/flights-from-old-chatham) - [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) - [Coxsackie Vacations](https://www.expedia.ca/Coxsackie.d183657.Destination-Travel-Guides) - [Visit Kinderhook](https://www.expedia.ca/Kinderhook.dx121767) - [Visit Malden Bridge](https://www.expedia.ca/Malden-Bridge.dx553248635975847470) - [Nassau Vacations](https://www.expedia.ca/Nassau.d3000449135.Destination-Travel-Guides) - [Visit Niverville](https://www.expedia.ca/Niverville.dx3000449167) - [Shaker Museum and Library](https://www.expedia.ca/Shaker-Museum-And-Library-Old-Chatham.d6087137.Vacation-Attraction) - [Visit Stottville](https://www.expedia.ca/Stottville.dx3000351293) - [Car rental Coxsackie](https://www.expedia.ca/Car-Rentals-In-Coxsackie.d183657.Car-Rental-Guide) - [Book Guest Houses in Chatham on Expedia.com](https://www.expedia.com/Chatham-Guest-Houses.d6046736-aaGuestHouses.Travel-Guide-Accommodation)