Title: Book the Best ROMANTIC Hotels in Stockbridge, MA from CA $115  - Stockbridge Romantic Getaways | 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 Romantic Hotels in Stockbridge, MA from CA $115

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## Check availability on Stockbridge Romantic Hotels

Tonight

[Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Tomorrow

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

## Our top choices for Stockbridge romantic 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)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.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)

![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

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

Stockbridge

8.8/10

Excellent

(1002)

"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "

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

Joyce

CA $197

CA $282 total

includes taxes & fees

Jan 12 - Jan 13, 2026

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

![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.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)

![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 (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.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)

"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 $526

CA $636 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![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)

![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)

### The Yankee, Trademark Collection by Wyndham

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

Lenox

9.2/10

Wonderful

(1002)

"Friendly staff, very clean room and super comfy bed"

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

Linda

CA $103

CA $115 total

includes taxes & fees

Dec 24 - Dec 25

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

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.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/1000000/10000/2100/2067/207845f4.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

(986)

"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"

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

Frank

CA $128

CA $143 total

includes taxes & fees

Dec 15 - Dec 16

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

![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

[](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

Lenox

9.0/10

Wonderful

(815)

"Easiest check in and out. Great food in dining room. "

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

William

CA $151

CA $169 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9becd207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Village Carriage House - Super Private!!

[](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information)

Lanesborough

9.8/10

Exceptional

(269)

"The cottage was amazing. Hope to be visit again and again. "

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

Mark M.

CA $186

CA $285 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/ffb7a388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbour House Inn

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

Cheshire

9.4/10

Exceptional

(53)

"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."

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

alton

CA $296

CA $313 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/6349c6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blackberry River Inn

[](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information)

Norfolk

9.4/10

Exceptional

(163)

"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."

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

Paulina

CA $226

CA $260 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/6d6c1dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually furnished, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/3c75b29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor wedding](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/8bcde002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, garden views ](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/720e4e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gedney Farm

[](https://www.expedia.ca/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information)

Great Barrington

9.2/10

Wonderful

(132)

"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."

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

Lynda

CA $255

CA $280 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2788df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/d5a96942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2435c38a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/a7eb284a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information)

Stephentown

8.4/10

Very good

(12)

"Great location and property. thank you"

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

Christine P.

CA $181

CA $346 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.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=2025-12-27&endDate=2025-12-28&regionId=162575&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true)

## Top Stockbridge Hotel Reviews

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

### The Red Lion Inn

10/10 Excellent

"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "

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

"Clean spacious toom"

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

"Great staff especially Katherine "

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

![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4_y.jpg)

### The Ponds at Foxhollow

10/10 Excellent

"There was a coffee machine but no filters nor beans. I wish they had been provided."

[](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.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)

![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg)

### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

10/10 Excellent

"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"

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

## Frequently asked questions

### Searching for romantic hotels in Stockbridge?

### When is the best time of year for a romantic getaway to Stockbridge?

### What is there to do in Stockbridge?

### What's the best way to get to Stockbridge and around town during my romantic getaway?

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