Title: Book the Best Monterey LUXURY Hotels - Upscale Hotels in Monterey, MA | 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)

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# Find luxury hotels in Monterey, MA

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## Check availability on Monterey Luxury Hotels

Tonight

[Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=6005411&startDate=2025-12-22&endDate=2025-12-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Tomorrow

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

This weekend

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

Next weekend

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

## Our top choices for Monterey luxury hotels

![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/21cb26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakehouse Inn

[](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information)

Lee

9.6/10

Exceptional

(290)

"A charming inn in the center of the Berkshires."

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

Danny

CA $250

CA $294 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/99b13181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/c81c0732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Central Downtown Inn & Suites

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

Pittsfield

8.6/10

Excellent

(346)

"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."

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

Lynn

CA $130

CA $145 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 33 Main

[](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information)

Lenox

10/10

Exceptional

(74)

"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."

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

James

CA $547

CA $612 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/edd6aeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gilded Stage in the Mainhouse](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/76b1fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Stockbridge

[](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)

Lee

9.8/10

Exceptional

(99)

"Well-run and elegant property. "

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

Steven

CA $346

CA $406 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.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)

![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)

### 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 $527

CA $638 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6cbad311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room #10 Queen's Cottage | Private kitchen](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/bbf9b83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Devonfield Inn B&B

[](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information)

Lee

10/10

Exceptional

(134)

"The inn has an excellent location and amenities."

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

Christopher

[](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information)

![Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/90de0046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room 194, 1 Queen bed, 1 Sofa bed, Courtyard View with balcony](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/d3c12b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/8a8cd518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/de957a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Old Inn On The Green

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information)

Great Barrington

9.2/10

Wonderful

(90)

"Beautiful Inn and outstanding chef"

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

Catherine

CA $421

CA $508 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/8d18b6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/w2999h2001x0y0-c0bff1cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marion Slocomb Suite, Cottage](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cd8fcdd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/175edf77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Terrace Inn

[](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information)

Lenox

9.0/10

Wonderful

(43)

"Beautiful historic house in a great location. Responsive owner. Great visit!"

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

Abby

CA $302

CA $337 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information)

![John Harney Suite](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/04d25b53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/b4a29500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/e0e21a5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/cccc903a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The White Hart

[](https://www.expedia.ca/Torrington-Hotels-The-White-Hart.h16725119.Hotel-Information)

Salisbury

9.6/10

Exceptional

(143)

"Great charming place, friendly, helpful staff"

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

David

CA $398

CA $457 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Torrington-Hotels-The-White-Hart.h16725119.Hotel-Information)

![The Parlor Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b4671c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Loft Suite | In-room dining](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/w5552h4162x0y0-c20c0fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Parlor Suite | Private kitchen](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b8c74868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/0b5f32ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 9 Academy 

[](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.Hotel-Information)

Salisbury

9.0/10

Wonderful

(10)

"Nice room. "

![South Korea](https://a.travel-assets.com/egds/marks/flags/kr.svg)

JeongHoon

CA $681

CA $784 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.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=2026-01-05&endDate=2026-01-06&regionId=6005411&adults=2&sort=LUXURY&star=40,50&openPlayBack=true)

## Top Monterey 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

"The room was super clean and comfortable. Nice television and great bathroom. Highly recommend!"

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

"Wonderful breakfast, amazing relaxing hot tub, Beautiful clean room, staff friendly very helpful. Will stay again !!"

[](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

"Everything was awesome"

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

"Very good"

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

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

### Quality Inn Great Barrington

10/10 Excellent

"The rooms were very clean and well kept. The beds were very comfortable. The breakfast: There was no cereal or variety of breads like bagels. Yogurts were great. I do give them the benefit of the doubt on this because it was an off week, in between holidays. It was very quiet. Staff was wonderful. We will definitely be back. "

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

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

### Hotel On North

10/10 Excellent

"Spacious rooms. Attentive staff. Free parking behind the hotel."

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

![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg)

### Howard Johnson by Wyndham Lenox

10/10 Excellent

"The room was clean, comfortable and the staff was friendly. For those who are afraid of vermin, there was NO SIGNS whatsoever of either bugs or other vermin.. It was CLEAN. This is a place that is no frills, but for what you're paying for you get a lot, and a comfortable place to rest your head. We would absolutely go back when we're visiting the Pittsfield area."

[](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information)

## Frequently asked questions

### Are you searching for a great accommodation for your luxury getaway to Monterey?

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