Title: Book the Best ROMANTIC Hotels in Monterey, MA from CA $116  - Monterey Romantic Getaways | Expedia.ca

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![Those secluded lakes and those 🍁🍁 reflections. #Berkshires will always have a special place in our hearts. To know more about our last visit in that region, click the link in bio👆. We are sure you'd be inspired to head there soon!

#Fall #VisitMA](https://images.trvl-media.com/place/6005411/d14ddb40-0f71-4bdc-94c8-ec7e415e11fb.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Fun Travelog

# Find Romantic Hotels in Monterey, MA from CA $116

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## Check availability on Monterey Romantic Hotels

Tonight

[Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=6005411&startDate=2025-12-23&endDate=2025-12-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Tomorrow

[Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=6005411&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6005411&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6005411&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

## Our top choices for Monterey 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

(1006)

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

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

Linda

CA $104

CA $116 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.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/1000000/10000/2100/2067/207845f4.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

(997)

"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 $127

CA $142 total

includes taxes & fees

Dec 25 - Dec 26

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

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

![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)

### The Red Lion Inn

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

Stockbridge

8.8/10

Excellent

(1002)

"Old time charm and hot tub under the stars"

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

Lori

CA $193

CA $278 total

includes taxes & fees

Jan 14 - Jan 15, 2026

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.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)

### Berkshires Untold

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

Lenox

9.0/10

Wonderful

(819)

"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 $168 total

includes taxes & fees

Dec 24 - Dec 25

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

![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/522482a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Cottage](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/10e70d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![43-inch LCD TV with digital channels, streaming services](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/406606bb.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

(165)

"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

Jan 5 - Jan 6, 2026

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/0ab1624d.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/afbb4318.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

(271)

"We enjoyed our stay. Excellent location to explore Western Mass!"

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

Charles D.

CA $186

CA $287 total

includes taxes & fees

Dec 28 - Dec 29

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

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/032d6bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/1691fc0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/e8790e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396823/cc86757f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enjoy a restful stay with fast internet, smart TV and the company of your pet.

[](https://www.expedia.ca/Winsted-Hotels-Enjoy-A-Restful-Stay-With-Fast-Internet.h72396823.Hotel-Information)

winsted

9.2/10

Wonderful

(46)

"Fantastic hosts and great facilities would highly recommend"

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

Steve

CA $123

CA $232 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Winsted-Hotels-Enjoy-A-Restful-Stay-With-Fast-Internet.h72396823.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)

![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)

![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)

### 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 29 - Dec 30

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

![Front of property](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/69e879d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bd7aa934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bbe2d3d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/47826e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gateways Inn & Restaurant

[](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information)

Lenox

8.0/10

Very good

(193)

"Very well kept property, nice restaurant and is in a great area"

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

Josephine

CA $218

CA $255 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information)

![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)

![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 (Parlour Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.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 $525

CA $635 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.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=2026-01-06&endDate=2026-01-07&regionId=6005411&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true)

## Top Monterey Hotel Reviews

![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

"Very good"

[](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

"Old time charm and hot tub under the stars"

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

"From check in to the room itself to parking and breakfast everything was wonderful!!"

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

## Frequently asked questions

### Searching for romantic hotels in Monterey?

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

### What is there to do in Monterey?

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

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- [Flights to The Berkshires ](https://www.expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)
- [Flights from Kitchener to The Berkshires ](https://www.expedia.ca/lp/flights/10579/6047665/kitchener-to-the-berkshires)
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- [The Berkshires Vacation Rentals ](https://www.expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)

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