Title: Book the Best LAKESIDE Hotels in Pittsfield in 2025 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d9478.Destination-Travel-Guides) ![Pittsfield which includes flowers and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105629-Pittsfield.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Lake Hotels in Pittsfield, MA from CA $172 - ![](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 Pittsfield Lake Hotels Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Lake Hotels ![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) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/21cb26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn Lee 9.6/10 Exceptional (287) "Great Views & Hospitality" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald CA $239 CA $281 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ponds at Foxhollow Lenox 8.6/10 Excellent (132) "Perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) krystle CA $267 CA $299 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/ec8e2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/edecce8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/4fb8018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere Hinsdale 9.8/10 Exceptional (33) "Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey E. CA $252 CA $618 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/52f8efbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/d9fe6b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/8e812ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!! Valatie 10/10 Exceptional (56) "Great spot on the lake. Super quiet and relaxing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vincent m. CA $378 CA $748 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/c2b10b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/4fa6909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/55f4a3e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/c7323063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A spectacularly charming LAKE HOUSE on gorgeous Burden Lake! Averill Park 10/10 Exceptional (3) "We can’t wait to come back! The lake house is so stunningly beautiful. Very clean and beds were comfortable. Michelle was super accommodating and made sure we had everything we needed. Everyone was so nice and made us feel comfortable and right at home!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MarissaI CA $870 CA $1,558 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Averill-Park-Hotels-A-Spectacularly-Charming-LAKE-HOUSE-On-Gorgeous-Burden-Lake.h93401870.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=9478&adults=2&location_highlights_explore=on_lake&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![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 Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Good value. A good place." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Hilton Garden Inn Lenox Pittsfield](//images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2_y.jpg) ### Hilton Garden Inn Lenox Pittsfield 10/10 Excellent "This is the second time that I’ve stayed there at this hotel and I will continue to stay there when I visit. I just wish and this is a personal preference that breakfast was included in the price." [](https://expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ## Frequently asked questions ### How much do lakeside hotels in Pittsfield cost? > The price for lakeside hotels in Pittsfield ranges from CA $172 to CA $1,558 per night. Whatever your budget, it's a cinch to find a perfect retreat by the water. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Are there any family-friendly lakeside hotels in Pittsfield? > Settle in at [The Black Swan Lee - Lenox, Ascend Hotel Collection](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) and make your escape to Pittsfield one to remember. This family-friendly lakeside hotel has a 3-star rating and features including complimentary breakfast and housekeeping services. After checking in and chilling in your comfy new digs, it's time to head out and start exploring. [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) and [Berkshire Museum](https://www.expedia.ca/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) are just two family-friendly attractions in Pittsfield. ### Why book your lakeside hotel in Pittsfield with Expedia? > Finding your ideal lakeside hotel in Pittsfield is a snap with Expedia. Getting away with the kids? Make your way to the filters to search for properties with family-friendly amenities. If you have a budget in mind, select how much you want to spend and your desired hotel star rating. Whatever your needs or travel plans, you'll always get the best deal possible. ### How can I find cheap lakeside hotels in Pittsfield? > Use Expedia's handy filters to set your price per night budget. Then, select your preferred hotel star rating — they range from basic (1 star) to luxury (5 star). You can also search based on specific areas you'd like to stay in. Scoring your ideal lakeside hotel in Pittsfield at the perfect price couldn't be easier! ### What is there to do in Pittsfield near my lakeside hotel? > Pittsfield has enough activities and sights to keep you entertained for weeks (or months!), starting with [Bousquet Ski Area](https://www.expedia.ca/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction). [Pittsfield State Forest](https://www.expedia.ca/Pittsfield-State-Forest-Pittsfield.d6339854.Vacation-Attraction), [Barrington Stage Company](https://www.expedia.ca/Barrington-Stage-Company-Pittsfield.d553248621532665294.Vacation-Attraction) and [Berkshire Museum](https://www.expedia.ca/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) are other renowned attractions. If you're sticking around a while, [Colonial Theater](https://www.expedia.ca/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction) and [Arrowhead Museum](https://www.expedia.ca/Arrowhead-Museum-Pittsfield.d6091847.Vacation-Attraction) will put the finishing touches on your itinerary. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Berkshire County](https://www.expedia.ca/Berkshire-County-Bed-And-Breakfast.d553248635083901436-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Berkshire County](https://www.expedia.ca/Berkshire-County-Chalets.d553248635083901436-aaChalets.Travel-Guide-Accommodation) - [Inns in Berkshire County](https://www.expedia.ca/Berkshire-County-Inns.d553248635083901436-aaInns.Travel-Guide-Accommodation) - [Resorts in Berkshire County](https://www.expedia.ca/Berkshire-County-Resort-Hotels.d553248635083901436-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Dalton](https://www.expedia.ca/Dalton-Apart-Hotels.d6911-aaApartHotels.Travel-Guide-Accommodation) - 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