Title: Book the Best Western Massachusetts LUXURY Hotels - Upscale Hotels in Western Massachusetts, MA | Expedia.ca [Western Massachusetts Travel Guide](https://expedia.ca/Western-Massachusetts.dx6234063)[Hotels in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels)[Vacation Rentals in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals)[Flights to Western Massachusetts](https://expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights)[Western Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide)[Western Massachusetts Vacation Packages](https://expedia.ca/Western-Massachusetts.d6234063.Destination-Travel-Guides) ![The Berkshires featuring snow as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71827-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Western Massachusetts, 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 Western Massachusetts Luxury Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-14&endDate=2025-10-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Western Massachusetts 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) ![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) ![Suite, Private Bathroom (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.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) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 Wonderful (107) "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. " CA $434 CA $525 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/080950ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/0750cd60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony Queen](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/1845c2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Northampton Northampton 9.2/10 Wonderful (1006) "Beautiful historic property with great dining options." CA $1,262 CA $1,410 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.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) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/802fba0f.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) ![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) ### The Orchards Hotel Williamstown 8.6/10 Excellent (442) [](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) ![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) ![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) ### 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... [](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/aca96762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/46ab504c.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) ### Wagon Wheel Inn Lenox 7.0/10 Good (633) "Convenient location for my trip" CA $111 CA $124 total includes taxes & fees Oct 15 - Oct 16 [](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) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.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) ### Hotel On North Pittsfield 9.6/10 Exceptional (779) "Great property! Very large clean room in a unique hotel! " CA $163 CA $182 total includes taxes & fees Nov 11 - Nov 12 [](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) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/d7cd7f22.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) ### 1896 House Country Inn & Motels Williamstown 6.6/10 (445) "Interesting cosy room, lovely seats on verandah, easy walk across bridge to Inn, easy tea and coffee maker." CA $132 CA $148 total includes taxes & fees Nov 12 - Nov 13 [](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) ![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) ![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) ![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 (1006) "Good breakfast King rooms are the best facing the mountains Recently remodeled " CA $188 CA $210 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/a37fc75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa Holyoke 9.4/10 Exceptional (2240) "The staff is wonderful both at the hotel and dining ! " CA $154 CA $179 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.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) ![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.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) ![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 (407) "That can be reserved at any time" CA $122 CA $137 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.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=2025-10-28&endDate=2025-10-29®ionId=6234063&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Western Massachusetts ### Western Massachusettsand its attractions for luxury travelers Western Massachusetts offers a delightful blend of cultural sophistication and natural beauty, perfect for luxury travellers seeking unique experiences. Start your journey in the historic town of Lenox, where the elegant Blantyre estate transports you to a world of refined leisure, surrounded by stunning gardens and the tranquil sounds of the Berkshires. Explore the renowned Tanglewood Music Center, where you can enjoy world-class performances under the stars, an experience that epitomises opulence and artistry. For a taste of local charm, visit the picturesque town of Stockbridge, home to the Norman Rockwell Museum, where you can immerse yourself in American art history. Nature enthusiasts will appreciate the breathtaking views from Mount Greylock, the highest peak in Massachusetts, which offers exhilarating hiking trails and serene picnic spots. After a day of exploration, unwind in the luxurious accommodations of the Canyon Ranch in Lenox, where guests are pampered with spa treatments and gourmet dining, ensuring a restorative and indulgent stay. With its rich history, vibrant arts scene, and unparalleled natural beauty, Western Massachusetts is a hidden gem waiting to be discovered by discerning travellers. ## Top Western Massachusetts Hotel Reviews ![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 "This place is just beyond incredible! It is our 40th wedding anniversary today and so happy we found this place. " [](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 very nice, clean and perfect location! Walked to all. My only issue was the ac did not work but I opened the windows so all was good. I would stay here again without a doubt. I recommend it as well. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 bar and restaurant were excellent. Valet parking is free and fast. Ive machines should be on each floor. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Beautiful stay! Great restaurant, great pool/hot tub/ breakfast on the patio! " [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Springfield MA](//images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg) ### La Quinta Inn & Suites by Wyndham Springfield MA 10/10 Excellent "The staff at this hotel was fabulous " [](https://expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](//images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "Very nice hotel for the price. Close to Yankee Candle. Have stayed here previously. Difficult to find the driveway in-very small sign-easy to miss." [](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Hilton Garden Inn-Springfield, MA](//images.trvl-media.com/lodging/1000000/900000/892100/892040/2726a1b6_y.jpg) ### Hilton Garden Inn-Springfield, MA 10/10 Excellent "So close to the hall of fame" [](https://expedia.ca/Springfield-Hotels-Hilton-Garden-Inn-Springfield.h892040.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 "Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!" [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Sheraton Springfield Monarch Place Hotel](//images.trvl-media.com/lodging/1000000/30000/21500/21419/74f0d068_y.jpg) ### Sheraton Springfield Monarch Place Hotel 10/10 Excellent "Nice place to stay. Pub food worst ever — eat elsewhere. 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