Title: Book the Best ROMANTIC Hotels in Western Massachusetts, MA from CA $137  - Western Massachusetts Romantic Getaways | 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 Romantic Hotels

Tonight

[Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-01-19&endDate=2026-01-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Tomorrow

[Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-01-20&endDate=2026-01-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

This weekend

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

Next weekend

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

## Our top choices for Western Massachusetts romantic hotels

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.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)

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.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)

### The Yankee, Trademark Collection by Wyndham

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

Lenox

9.2/10

Wonderful

(1,004 reviews)

"Great stay!"

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

Ann

CA $129

CA $144 total

includes taxes & fees

Jan 27 - Jan 28

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f7391fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/be33985c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/261a7ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/bc7070b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn on Boltwood

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

Amherst

9.4/10

Exceptional

(758 reviews)

"Idyllic New England inn…. Cozy, super clean, great restaurant on the property, roaring fireplace, great way to spend weekend with family over the holidays!"

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

Eileen

CA $271

CA $303 total

includes taxes & fees

Jan 25 - Jan 26

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

![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)

![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

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

Holyoke

9.4/10

Exceptional

(2,231 reviews)

"Great room and location."

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

Karina

CA $162

CA $188 total

includes taxes & fees

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4e4268ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3e2d816d.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

(1,003 reviews)

"Old time charm and hot tub under the stars"

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

Lori

CA $209

CA $296 total

includes taxes & fees

Jan 25 - Jan 26

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

![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)

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

(1,006 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

Jan 23 - Jan 24

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

![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.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)

![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.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

(839 reviews)

"Great hospitality and beautiful design. Our family had a great time!"

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

Alison

CA $123

CA $137 total

includes taxes & fees

Jan 20 - Jan 21

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

![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

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

Northampton

9.2/10

Wonderful

(1,001 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

CA $230

CA $256 total

includes taxes & fees

Jan 20 - Jan 21

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/30e56504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Williams Inn

[](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information)

Williamstown

9.6/10

Exceptional

(563 reviews)

"Very pleasant and relaxing place to stay"

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

steve

CA $256

CA $287 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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)

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

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/3670f3af.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)

### Harbour House Inn

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

Cheshire

9.4/10

Exceptional

(53 reviews)

"Nice place for a weekend away."

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

Gregory

CA $287

CA $304 total

includes taxes & fees

Jan 21 - Jan 22

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

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

![Lobby sitting area](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/c08e3534.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

(134 reviews)

"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 $258

CA $283 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Great-Barrington-Hotels-Gedney-Farm.h41178000.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=2026-02-02&endDate=2026-02-03&regionId=6234063&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true)

## Find out more about Western Massachusetts

### Western Massachusetts attractions for couples

Western Massachusetts offers a delightful blend of natural beauty and cultural experiences perfect for quality-seeking travellers. Begin your adventure in the picturesque town of Stockbridge, home to the Norman Rockwell Museum, where you can immerse yourself in the iconic American art of the beloved illustrator. Just a short drive away, the rolling hills of the Berkshires invite you to hike scenic trails or enjoy a leisurely picnic at Tanglewood, the summer home of the Boston Symphony Orchestra, where you might catch a live performance under the stars. For families, the Eric Carle Museum of Picture Book Art in Amherst is a whimsical experience that sparks creativity in both children and adults alike. History buffs will appreciate a visit to the historic village of Northampton, known for its vibrant arts scene and charming shops, while outdoor enthusiasts can explore the stunning landscapes of Mount Greylock State Reservation, the highest peak in Massachusetts, offering breathtaking views and a chance to connect with nature. To make the most of your stay, consider lodging in the charming town of Lenox, where upscale hotels and quaint inns provide a perfect retreat after a day of exploration, allowing you to unwind in comfort while enjoying attentive service that enhances your overall experience.

## 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

"Fireplace is a nice touch "

[](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

"Yes "

[](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

"Staff was very courteous and rooms clean."

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

"Absolutely fabulous!"

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

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