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

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![Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA.

Significant collection of the artist's original work & memorabilia on display in his hometown.](https://images.trvl-media.com/place/162575/de09378b-b417-4c3e-9c9a-1f58d65ad2fd.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by William Keller

# Find Historic Hotels in Stockbridge, MA from CA $264

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## Check availability on Stockbridge Historic Hotels

Tonight

[Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-04&endDate=2025-12-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Stockbridge Historic Hotels

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

Stockbridge

8.8/10

Excellent

(1000)

"I love the ambience - historic and comfortable and excellent food. "

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

Nancy

CA $180

CA $264 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Lobby](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/0ab8f96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/ea4dc35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/8eb2abf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/2fdc0476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Kenmore Hall

Richmond

10/10

Exceptional

(27)

"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "

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

Margaret

CA $593

CA $651 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/a110f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/2a4ba750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9abb62fb_edited_7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock

10/10

Exceptional

(23)

"This property is spacious, clean and well- appointed. I would stay here again!"

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

Amanda M.

CA $147

CA $329 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.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=2025-12-18&endDate=2025-12-19&regionId=162575&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Stockbridge Hotel Reviews

![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

"Everyone was Curtieus and very helpful !!! Room was very clean and nice!!!! Would be glad to stay again !!!! Thank You for making our stay pleasant and welcoming !!!! To all of the staff, Have A Great. Holiday Season !!!!! "

[](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

"Great stay, great breakfast"

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

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

### Quality Inn

10/10 Excellent

"Clean room, staff friendliness, near store and amenities."

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

"Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! "

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

"Loved having coffee and tea 24/7"

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

![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg)

### Monument Mountain Motel

10/10 Excellent

"The rm was perfect. Bed, table and chairs, tv, and good size bath. Was here 3 days to see family. Very friendly,comfortable bed and very clean. Walking distance to supermarket and dining and bowling. I will rent again."

[](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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

"Everything was a great experience "

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

"Everything was great. "

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

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

### Hotel On North

10/10 Excellent

"Wonderful stay, as usual. I have business in the Pittsfield area, 3 or 4 times a year and wouldn’t think of staying anywhere else. Quiet, comfortable….staff is always helpful and friendly….restaurant in the building is just another plus."

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

## Frequently asked questions

### What should a history enthusiast expect from a trip to Stockbridge?

### What's the best place to stay in Stockbridge that's close to historical sites?

### How many historically relevant hotels are there in Stockbridge?

### What are the top historical places and other sights to visit in Stockbridge?

### What is a historic hotel like in Stockbridge?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Stockbridge have modern facilities?

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