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)

![A panorama of western Massachusetts from the top of Mount Greylock](https://images.trvl-media.com/place/6234063/25d665be-4bef-4d30-84bb-d5865c866e81.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6234063/25d665be-4bef-4d30-84bb-d5865c866e81.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Western Massachusetts Luxury Hotels

Tonight

[Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-01-23&endDate=2026-01-24&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Tomorrow

[Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-01-24&endDate=2026-01-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

This weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-01-23&endDate=2026-01-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Next weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

## Our top choices for Western Massachusetts luxury hotels

![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)

![Suite, Private Bathroom (Parlour Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.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

[](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information)

Stockbridge

9.2/10

Wonderful

(110 reviews)

"Great breakfast, friendly helpful staff, pretty yard, good location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deborah

CA $427

CA $516 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/73ad73a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/0d0e7da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/35aa91d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/6a901d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Northampton

[](https://www.expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

Northampton

9.2/10

Wonderful

(1,002 reviews)

"Perfect hotel choice for attending an event at Iron Horse \~ clean room, lovely staff and great central location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Renee

[](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/1000000/10000/8800/8739/192c9e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/c234a028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/27d5352c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Orchards Hotel

[](https://www.expedia.ca/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information)

Williamstown

8.6/10

Excellent

(442 reviews)

"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/ed0acf17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/859f5f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Jetted Tub](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/8ea10947.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

[](https://www.expedia.ca/Great-Barrington-Hotels-Lantern-House-Motel.h11537599.Hotel-Information)

Great Barrington

8.2/10

Very good

(455 reviews)

"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)

![Double Room | View from room](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/2f62b663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed (Jaccuzzi) | Jetted tub](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/d981b422.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)

![Front of property](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/f62aa44d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wagon Wheel Inn

[](https://www.expedia.ca/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information)

Lenox

7.0/10

Good

(641 reviews)

"Clean, comfortable older motel. Not fancy but a good place to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Woodrow

[](https://www.expedia.ca/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library Suite, 1 King Bed](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c5c7040f.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)

![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e65bd9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel On North

[](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

Pittsfield

9.6/10

Exceptional

(820 reviews)

"Great staff, room was huge and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cameron

CA $204

CA $228 total

includes taxes & fees

Jan 27 - Jan 28

[](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/19000000/18680000/18670300/18670223/68872253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/b07cfd29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/39fc54d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1896 House Country Inn & Motels

[](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information)

Williamstown

6.6/10

(448 reviews)

"Place was convenient, cleaned and quiet a little old, but all in all a good stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelley

[](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)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.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)

![Premier Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

[](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

Lenox

9.2/10

Wonderful

(1,011 reviews)

"Very friendly staff comfy beds!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Giselle

CA $127

CA $142 total

includes taxes & fees

Feb 2 - Feb 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)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/efe975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive King Room](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/4ae0b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### D. Hotel Suites & Spa

[](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

Holyoke

9.2/10

Wonderful

(2,243 reviews)

"Great, great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Richard

CA $165

CA $192 total

includes taxes & fees

Jan 26 - Jan 27

[](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)

![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/6d051282.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)

### Sunset Inn

[](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information)

Lee

7.6/10

Good

(411 reviews)

"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly

CA $130

CA $145 total

includes taxes & fees

Feb 6 - Feb 7

[](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=2026-02-07&endDate=2026-02-08&regionId=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](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Room is great for families. Bit dated but clean and spacious."

[](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg)

### D. Hotel Suites & Spa

10/10 Excellent

"Excellent"

[](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"generally good"

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. "

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Inn on Boltwood](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f10073da_y.jpg)

### Inn on Boltwood

10/10 Excellent

"It is a beautiful and historic property with an amazing restaurant and bar."

[](https://expedia.ca/Springfield-Hotels-Inn-On-Boltwood.h2027065.Hotel-Information)

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg)

### Hotel On North

10/10 Excellent

"Everything was very good. The room was clean and cozy."

[](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Very clean...i dotted and t crossed"

[](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information)

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg)

### Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Staff was pleasant and helpful, room spacey and all immaculate ."

[](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information)

![Marriott Springfield Downtown](https://images.trvl-media.com/lodging/1000000/10000/6300/6279/c4768c07_y.jpg)

### Marriott Springfield Downtown

10/10 Excellent

"Clean"

[](https://expedia.ca/Springfield-Hotels-Tower-Square-Hotel-Springfield.h6279.Hotel-Information)

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