Title: Book the Best SHOPPING Hotels in Stockbridge in 2026 | Expedia.ca

[Stockbridge Travel Guide](https://expedia.ca/Stockbridge.dx162575)[Hotels in Stockbridge](https://expedia.ca/Stockbridge-Hotels.d162575.Travel-Guide-Hotels)[Vacation Rentals in Stockbridge](https://expedia.ca/Stockbridge-Vacation-Rentals.d162575.Travel-Guide-VacationRentals)[Flights to Stockbridge](https://expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)[Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)[Stockbridge Vacation Packages](https://expedia.ca/Stockbridge.d162575.Destination-Travel-Guides)

![autumn in the mountains](https://images.trvl-media.com/place/162575/19bfb038-826c-4b9c-9660-31de551f85b1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/162575/19bfb038-826c-4b9c-9660-31de551f85b1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Stockbridge Shopping Hotels

Tonight

[Feb 25 - Feb 26](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-02-25&endDate=2026-02-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 26 - Feb 27](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Stockbridge hotels with shopping nearby

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk into town, soak up sun on enclosed porch & steps away from nature trails!

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

Stockbridge

10/10

Exceptional

(34 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

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

cathy c.

CA $409

CA $875 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.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)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.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/a97806ae.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

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

Pittsfield

8.0/10

Very good

(1,000 reviews)

"Staff was very courteous and rooms clean."

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

Steven

CA $136

CA $152 total

includes taxes & fees

Feb 28 - Mar 1

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

![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Great Barrington Berkshires

[](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

Great Barrington

7.6/10

Good

(572 reviews)

"Excellent location!!"

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

Abdul Samad

CA $103

CA $115 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.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/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Tanglewood: Historic Summer Retreat

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

New Lebanon

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

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

Paul S.

CA $155

CA $469 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/d08b3a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/bdfc25ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/98afb96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/ecc89925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

[](https://www.expedia.ca/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information)

Hancock

10/10

Exceptional

(6 reviews)

"Great room decorations, travel with two kids they have a great time playing video games"

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

Andres

CA $144

CA $321 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Ski Getaway in the Berkshires

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

Great Barrington

9.0/10

Wonderful

(11 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

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

Cristine C.

CA $277

CA $431 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/1df26d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Berkshires Home Near Tanglewood, Trails & Wineries

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

Lebanon Springs

9.0/10

Wonderful

(21 reviews)

"Comfy beds, clean, great big deck with a view. "

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

Corinne T.

CA $170

CA $488 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

Hancock

8.2/10

Very good

(989 reviews)

"nice and clean, good customer service, but the room is smell. "

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

Huang

CA $259

CA $289 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sweet Cozy Victorian in Housatonic. Close to everything. 

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

Housatonic

10/10

Exceptional

(3 reviews)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

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

Cheryl F.

CA $185

CA $366 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/2802a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/e715a827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/f0716890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/58aa3713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Barn Retreat — All-Season Escape Awaits!

[](https://www.expedia.ca/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information)

East Chatham

10/10

Exceptional

(2 reviews)

"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "

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

Timothy S.

CA $459

CA $856 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.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=2026-03-11&endDate=2026-03-12&regionId=162575&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_162575)

## Top Stockbridge Hotel Reviews

![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

"Clean room, breakfast was good👍"

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Affordable price, clean bedroom and close to everything. "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38_y.jpg)

### The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"The staff was wonderful "

[](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

![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

"Yes it was clean as usual."

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

![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"Clean, breakfast was a nice option before heading to Butternut mountain nearby "

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"convenient location, wonderful breakfast, very clean and comfortable"

[](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"great customer service"

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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

"Bathroom had somebody’s hair on the door and shower "

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

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- [Flights to Great Barrington ](https://www.expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights)
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- [Flights from Lenox ](https://www.expedia.ca/lp/flights/8587/flights-from-lenox)

- [Great Barrington Vacations ](https://www.expedia.ca/Great-Barrington.d110336.Destination-Travel-Guides)
- [Visit Great Barrington ](https://www.expedia.ca/Great-Barrington.dx110336)
- [Lake Mansfield Park ](https://www.expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction)
- [Lenox Library ](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction)
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- [Richmond Vacations ](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides)
- [Visit South Lee ](https://www.expedia.ca/South-Lee.dx183343)
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- [Avis Rental Cars in Lenox ](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers)
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- [Enterprise Rental Cars in Great Barrington ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Great-Barrington.d110336-c15.Car-Rental-Guide-Suppliers)

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