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Check prices for these dates

Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14
In one month
Dec 26 - Dec 28
In two months
Jan 23 - Jan 25

B&B in Monterey

Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,399
￥18,859 total
includes taxes & fees
Dec 4 - Dec 5
Locust Tree Bed and Breakfast LLC
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (161)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥25,668
￥29,518 total
includes taxes & fees
Dec 1 - Dec 2
Blackberry River Inn
Interior detail
Manor House Inn

Manor House Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is ￥49,329
￥54,755 total
includes taxes & fees
Dec 7 - Dec 8
Manor House Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥28,737
￥33,704 total
includes taxes & fees
Dec 4 - Dec 5
Lakehouse Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is ￥22,518
￥25,153 total
includes taxes & fees
Dec 9 - Dec 10
Wilder House Berkshires
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is ￥42,918
￥50,336 total
includes taxes & fees
Dec 24 - Dec 25
The Inn at Stockbridge
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
The price is ￥31,080
￥34,716 total
includes taxes & fees
Dec 4 - Dec 5
Granville House
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox
The price is ￥35,500
￥51,518 total
includes taxes & fees
Dec 21 - Dec 22
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is ￥16,344
￥17,929 total
includes taxes & fees
Dec 2 - Dec 3
Shaker Mill Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ￥66,582
￥74,373 total
includes taxes & fees
Dec 31 - Jan 1, 2026
33 Main
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1003)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ￥22,116
￥30,809 total
includes taxes & fees
Dec 21 - Dec 22
The Cornell Inn, Lenox & The Berkshires
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is ￥34,203
￥34,203 total
includes taxes & fees
Dec 1 - Dec 2
Tanglewood Suites
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

4.5 star property
Stockbridge
9.2 out of 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
Robert
The price is ￥59,648
￥72,157 total
includes taxes & fees
Dec 14 - Dec 15
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is ￥35,500
￥51,518 total
includes taxes & fees
Dec 21 - Dec 22
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.

Lenox
The price is ￥47,447
￥66,432 total
includes taxes & fees
Dec 1 - Dec 2
Elegant Carriage House room with a queen bed and private patio.
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is ￥24,833
￥27,813 total
includes taxes & fees
Dec 1 - Dec 2
Inn at Silver Maple Farm
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is ￥40,810
￥58,321 total
includes taxes & fees
Dec 21 - Dec 22
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is ￥43,465
￥61,635 total
includes taxes & fees
Dec 21 - Dec 22
Historic Susan B. Anthony Room - Cozy & Charming Stay
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.
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Top Monterey Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Great stay, great breakfast"
Peter 1-night trip
Posted 8 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Monterey

Monterey B&B information

Number of reviews
2,994
Accommodation
38 B&B
Lowest Price
￥17,929
Highest Price
￥74,373

Frequently asked questions

Searching for B&Bs in Monterey?
If you're looking for something a little quirkier than the traditional hotel experience, a bed and breakfast could be a great option for your vacation. When you want to venture out to explore Monterey, consider browsing the exhibits at Bidwell House Museum.
Why choose B&Bs instead of traditional hotels?
Every B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook, the small details are what make bed and breakfasts a home away from home.
What are the best bed and breakfasts in Monterey?
Below are some well-liked B&Bs in the area: Blackberry River Inn: 14 rooms. 12 mi (19.3 km) from the heart of Monterey. Enjoy the free cooked breakfast and outdoor pool. The Cornell Inn, Lenox & The Berkshires: 13.4 mi (21.6 km) from the downtown core. Enjoy the free full breakfast and unique décor. Shaker Mill Inn: 9 rooms. Situated 13.5 mi (21.7 km) from the heart of Monterey. Chambery Inn: 9 rooms. 9.2 mi (14.8 km) from the heart of downtown. Enjoy the private yard and deli. Locust Tree Bed and Breakfast LLC: 7 rooms. Located 12.1 mi (19.5 km) from the core of Monterey.
When should I book my B&B in Monterey?
When you're planning your stay in Monterey, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Monterey are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Monterey?
When you want to explore some things to do in Monterey, consider a visit to Bidwell House Museum. Lake Buel and Ski Butternut are also some sites to visit if you want to see more of the area.
How can I get to and around Monterey?
You can plan your excursions in and around Monterey ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 17.5 mi (28.1 km) from the city center. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 25.3 mi (40.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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