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Compare 30 B&B in Monterey with updated reviews, rates, and availability.

The Cornell Inn, Lenox

3.0 star property
8.8 out of 10, Excellent, (1046)
"We were greeted warmly upon arrival with hot beverages and brownies. There were bakery items available all during our stay, and the property features a quaint little bar with many offerings. The breakfast was served in a bright and very well-appointed room with a fireplace and the staff were very friendly and attentive. The food was very nicely presented and delicious. This is a wonderful bed and breakfast at a very affordable price. Will definitely return. "
The price is AED 448
AED 526 total
includes taxes & fees
3 Dec - 4 Dec
The Cornell Inn, Lenox

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (91)
"The room with bathroom was very comfortable and clean. The property was extensive and well maintained. Breakfast choices were extensive and our choices were delicious and cooked by Lucas."
The price is AED 606
AED 681 total
includes taxes & fees
15 Dec - 16 Dec
Blackberry River Inn

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (367)
"It was okay"
The price is AED 386
AED 444 total
includes taxes & fees
5 Dec - 6 Dec
Locust Tree Bed and Breakfast LLC

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is AED 555
AED 650 total
includes taxes & fees
20 Dec - 21 Dec
Lakehouse Inn

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (400)
"Quaint "
The price is AED 533
AED 584 total
includes taxes & fees
1 Dec - 2 Dec
Shaker Mill Inn

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is AED 628
AED 702 total
includes taxes & fees
8 Dec - 9 Dec
Brook Farm Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is AED 698
AED 779 total
includes taxes & fees
1 Dec - 2 Dec
Chambery Inn

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (10)
"Great place, very clean, hospitable and designed with impeccable taste. "
The price is AED 571
AED 637 total
includes taxes & fees
5 Dec - 6 Dec
Wilder House Berkshires

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 1,285
AED 1,436 total
includes taxes & fees
1 Dec - 2 Dec
33 Main

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
The price is AED 668
AED 816 total
includes taxes & fees
8 Dec - 9 Dec
Whistler's Inn Bed & Breakfast

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (117)
"Arrived Friday to see a Tanglewood concert. Inn provided lovely afternoon cocktails and appetizers with piano music. Saturday hosts sponsored garden concert with local artists - really nice after morning hike to water fall and early afternoon golf. Yummy Morning breakfast each day. Central to Stonebridge and Lenox. Hosts very knowledgeable "
The price is AED 1,062
AED 1,186 total
includes taxes & fees
3 Dec - 4 Dec
Devonfield Inn B&B

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (79)
"Everything "
The price is AED 584
AED 631 total
includes taxes & fees
1 Dec - 2 Dec
Inn at Silver Maple Farm

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"A charming old manor from the Gilded Age, thoughtfully updated and modernized without losing the soul of the original home. Incredibly comfortable rooms, inviting common spaces, excellent breakfast, beautiful grounds, and friendly staff. We especially enjoyed the fireplace in our room. Perfect for a romantic getaway, we look forward to visiting again in the future."
Manor House Inn

Granville House

3.0 star property
10.0 out of 10, Exceptional, (76)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is AED 735
AED 821 total
includes taxes & fees
1 Dec - 2 Dec
Granville House

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is AED 804
AED 804 total
includes taxes & fees
28 Nov - 29 Nov
Tanglewood Suites

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,685
AED 2,039 total
includes taxes & fees
29 Nov - 30 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge

Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible

9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
28 Nov - 29 Nov
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible

Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires

2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is AED 3,673
AED 4,685 total
includes taxes & fees
28 Nov - 29 Nov
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
Inn at Kenmore Hall
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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Other property types in Monterey

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 536
AED 821 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.

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. If your ideal vacation to Monterey includes spending lots of time outside, Beartown State Forest and Bidwell House Museum are good spots to enjoy the scenery.
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: The Cornell Inn, Lenox: 13.4 mi (21.6 km) from the heart of Monterey. Enjoy the free full breakfast and unique décor. Blackberry River Inn: 14 rooms. 12 mi (19.3 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 12.1 mi (19.5 km) from the heart of Monterey. Lakehouse Inn: 14 rooms. 10.5 mi (16.8 km) from the heart of downtown. Enjoy the free full breakfast and deli. Shaker Mill Inn: 9 rooms. Located 13.5 mi (21.7 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?
Spend some time exploring Beartown State Forest and Bidwell House Museum if you’re hoping to see some of the area’s natural features. 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.