Title: Book the Best Cheshire Hotels with FREE BREAKFAST in 2025 | 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) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # Find Hotels with Free Breakfast in Cheshire, MA from CA $108 - ![](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 availability on Cheshire Hotels with Free Breakfast Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-03&endDate=2025-11-04&adults=2&amenities=FREE_BREAKFAST&mealPlan=FREE_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-04&endDate=2025-11-05&adults=2&amenities=FREE_BREAKFAST&mealPlan=FREE_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=FREE_BREAKFAST&mealPlan=FREE_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=FREE_BREAKFAST&mealPlan=FREE_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire Hotels with Free Breakfast ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/ffb7a388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/d973dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn Cheshire 9.4/10 Exceptional (52) "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorie CA $342 CA $362 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1023) "I have stayed here many times and it is consistently a comfortable, clean and quiet place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanine CA $131 CA $146 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn West Stockbridge 9.6/10 Exceptional (433) "Very casual and easy check in and out; lovely and substantial breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie CA $141 CA $155 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.6/10 Exceptional (9) "Very friendly with dog. No complaints with accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lilian CA $189 CA $211 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/b5e2455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/9aabb83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee 8.4/10 Very good (1007) "Fine lodging for short term business stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $130 CA $145 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (938) "Enjoyable stay. Staff were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire CA $144 CA $161 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/45e111cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/2c0ca8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/488c62c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/6203d3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villager Motel Williamstown 8.8/10 Excellent (755) "It's very good for stay over" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frances CA $97 CA $108 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1007) "We had a lakeside room which was wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $154 CA $172 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/caece0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/5062d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel Williamstown 9.2/10 Wonderful (877) "Clean and friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $105 CA $124 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/c64cd286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/52ce390c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds | View from room](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/44b0e4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/9d6fa2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel Williamstown 9.6/10 Exceptional (582) "Pool, fire pit, grounds and staff were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy CA $139 CA $155 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.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=2025-11-17&endDate=2025-11-18®ionId=6005398&adults=2&mealPlan=FREE_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Everything was fine just no shampoo in the dispencer" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 and friendly " [](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 "Staff was friendly, nice area, near things but set back so you didn’t hear the traffic." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "The restaurant was so delicious …the fries were the best fries I have ever had …will never forget how tasty they were !!!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Porches Inn at Mass MoCA](//images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "peaceful" [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg) ### Quality Inn 10/10 Excellent "Everything great but breakfast needs an overhaul. Fresh fruit get rid of the sugar cereals. Eggs maybe? " [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![FairBridge Inn Express](//images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f_y.jpg) ### FairBridge Inn Express 10/10 Excellent "Heating fine. Room warm" [](https://expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![Harbour House Inn](//images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47_y.jpg) ### Harbour House Inn 10/10 Excellent "The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people." [](https://expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ## Frequently asked questions ### What's it like to take a trip to Cheshire? > Enjoy a complimentary breakfast in your Cheshire hotel, then hit the pavement to take in everything this location has to offer. Cheshire is known for its ski areas and restaurants. ### What are a few of the most popular free breakfast hotels in Cheshire? > [Harbour House Inn](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) is a popular B&B featuring free breakfast and free WiFi. ### How many hotels with free breakfast are there to pick from in Cheshire? > Though Cheshire only has 1 free breakfast hotel, you can browse our 5 other lodging options. ### What are the top places to visit in Cheshire? > After you've had a hearty breakfast, see what awaits you in Cheshire. Mount Greylock State Reservation is one of the attractions that makes Cheshire unique. ### What are free breakfast hotels in Cheshire like? > Whether or not you're a morning person, a free breakfast can help you get your Cheshire vacation off to a good start. Choosing a hotel with free breakfast is also a simple way to stick to your budget. 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