Title: Book the Best The Berkshires LUXURY Hotels - Upscale Hotels in The Berkshires, MA | Expedia.ca [The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Vacation Rentals in The Berkshires](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) ![The Berkshires which includes flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71831-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in The Berkshires, MA - ![](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 The Berkshires Luxury Hotels Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-01&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-02&endDate=2025-11-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top The Berkshires Luxury Hotels ![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 Wonderful (109) "Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $434 CA $525 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/9f24830b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/e0d92284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/36aa7821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/5446facc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Orchards Hotel Williamstown 8.6/10 Excellent (442) "A little dated. Restaurant shut down for renovations, disappointing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/74a22cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/7b898eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/7b1e7c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/15d50d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lantern House Motel Great Barrington 8.2/10 Very good (455) "The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen [](https://www.expedia.ca/Great-Barrington-Hotels-Lantern-House-Motel.h11537599.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/75f1ed66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/1ddc8409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/aca96762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | View from room](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/6d6cf248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wagon Wheel Inn Lenox 7.0/10 Good (640) "There was a mouse in our room at night." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brin CA $96 CA $108 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (788) "Clean modern place in town, good value. Room on street side was a little noisy at night, ask for back room if light sleeper. Restaurant was not good value. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $187 CA $209 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ed652faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/67356bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, Ensuite (Early American Suite 201)](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/366b65ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ba469908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1896 House Country Inn & Motels Williamstown 6.6/10 (448) "The price is good. It's a classic motel from the '50's, but gets the job done." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) edson [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1025) "Great place. Friendly staff and very well located. Great breakfast options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abiezer CA $150 CA $167 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/219cd416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/d1430bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/483e190d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Lee 7.6/10 Good (408) "The staff is a one man operation,Which he is a very nice man,does a good job keeping up with the cleaning.Location is great walking distance to the town and plenty of restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie CA $126 CA $141 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.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) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.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 (581) "Pool, fire pit, grounds and staff were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy CA $138 CA $155 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox Lenox 7.6/10 Good (816) "Staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $110 CA $123 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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=2025-11-15&endDate=2025-11-16®ionId=6047665&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about The Berkshires ### The Berkshiresand its attractions for luxury travelers The Berkshires beckons luxury travellers with its rich tapestry of culture, nature, and refined experiences. Begin your journey at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances in an idyllic outdoor setting. For art enthusiasts, the Norman Rockwell Museum in Stockbridge offers an intimate glimpse into the life and works of the beloved American painter, complemented by picturesque gardens. Outdoor adventurers can explore the stunning landscapes of Mount Greylock, the highest peak in Massachusetts, with opportunities for hiking, picnicking, and breathtaking vistas. Indulge in a day of pampering at the renowned Canyon Ranch, a wellness resort that offers a range of spa treatments and fitness classes tailored to rejuvenate body and mind. Finally, immerse yourself in the region’s culinary scene by dining at the exquisite Blantyre, a luxurious estate that transforms fine dining into an art form. For accommodation, the charming town of Lenox is particularly appealing, featuring elegant hotels and inns that blend classic New England charm with modern luxury. Here, you can unwind in opulent surroundings, perhaps enjoying a glass of wine beside a crackling fire after a day of exploration, while attentive staff cater to your every need. ## Top The Berkshires Hotel Reviews ![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) ![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 "Good location; reasonable price; very clean and quiet - would definitely return" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "It was really nice staying here. The room was clean, bed was comfortable, and there was a mini-fridge that wasn't full of expensive drinks you're not supposed to touch! It was mostly quiet, except for the trains at night that pass behind the building. It is very close by to shops, cool architecture, and a nice walking path. Very safe area too. The breakfast wasn't the best, but it's free, and you can easily pop in to nearby restaurants if you want something better. The staff are very friendly and helpful. I would recommend staying here! It's a nice place to stay for the price." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Excellent front desk staff. Ask for Steve. Very convenient to Monument Mountain and local ski resorts." [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![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 "I have stayed here many times and it is consistently a comfortable, clean and quiet place." [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 place. Friendly staff and very well located. Great breakfast options. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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) ![Howard Johnson by Wyndham Lenox](//images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "Coffee maker looks like it has mold inside " [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Otis](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Massachusetts](https://www.expedia.ca/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Lazy River in Massachusetts](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-A-Lazy-River.0-0-d223-tHotelswithaLazyRiver.Hotel-Filter-Destinations) - [Hotels with Free Breakfast in Massachusetts](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-Free-Breakfast.0-0-d223-tHotelswithFreeBreakfast.Hotel-Filter-Destinations) - [Mountain Hotels in Massachusetts](https://www.expedia.ca/Destinations-In-Massachusetts-Mountain-Hotels.0-0-d223-tMountainHotels.Hotel-Filter-Destinations) - 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