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Search B&B in Middlefield

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Compare 29 B&B in Middlefield with updated reviews, rates, and availability.

The Ellery
3.5 star property
9.0 out of 10, Wonderful, (531)
"Only negative I have is couple above our room must’ve lived in a barn I’m a big guy and try to walk cautiously at night not to disturb.these people kept walking as if walking with boots till about 1or 2 am. Not hotel’s fault some people are just unique lol. The bed was very comfortable,hot water in shower,tub combo.i didn’t do breakfast but even after hours tea and few items available if needed."
The price is AED 511
AED 570 total
includes taxes & fees
17 Nov - 18 Nov
The Ellery
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1000)
"Perfect romantic spot for a weekend getaway. Close enough to walk into town but far enough from crowds "
The price is AED 448
AED 526 total
includes taxes & fees
17 Nov - 18 Nov
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is AED 547
AED 642 total
includes taxes & fees
16 Nov - 17 Nov
Lakehouse 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
17 Nov - 18 Nov
Chambery Inn
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (471)
"This bed and breakfast is a true gem, set in a beautifully preserved 1836 mansion. The rooms feature herringbone wood floors, diamond-pane windows, and soaring 11-inch ceilings, creating an atmosphere that feels both magical and timeless. With its charming, historic details and exceptionally friendly owners, staying here is like stepping into an enchanting, old-world retreat."
The price is AED 509
AED 638 total
includes taxes & fees
18 Nov - 19 Nov
Whistler's Inn Bed & Breakfast
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (121)
"Stayed only one night Very cosy, quiet place "
The price is AED 592
AED 662 total
includes taxes & fees
17 Nov - 18 Nov
The Trail in Adams - Berkshires’ Art Hotel
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (399)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is AED 533
AED 584 total
includes taxes & fees
17 Nov - 18 Nov
Shaker Mill Inn
Old Mill Inn
3.0 star property
9.4 out of 10, Exceptional, (463)
"Beautiful place. Great staff. Clean and convenient "
The price is AED 696
AED 778 total
includes taxes & fees
18 Nov - 19 Nov
Old Mill 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
18 Nov - 19 Nov
Granville House
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
26 Nov - 27 Nov
33 Main
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 713
AED 796 total
includes taxes & fees
26 Nov - 27 Nov
Brook Farm Inn
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (117)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is AED 988
AED 1,104 total
includes taxes & fees
17 Nov - 18 Nov
Devonfield Inn B&B
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 963
AED 1,018 total
includes taxes & fees
18 Nov - 19 Nov
Harbour House Inn
Eastgate Inn B&B
2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
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
16 Nov - 17 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
17 Nov - 18 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
16 Nov - 17 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
16 Nov - 17 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 Middlefield

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is AED 620
AED 717 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is AED 542
AED 594 total
includes taxes & fees
17 Nov - 18 Nov
Jiminy Peak Mountain Resort
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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 Middlefield?
If you want to find a place to stay with fewer rooms than a hotel and an intimate environment, a B&B may be the perfect thing for your vacation to Middlefield. When you want to explore some attractions in town, Skyline Trail and Fox Den Wildlife Management Area are worth a stop.
Why should you consider B&Bs instead of traditional hotels?
B&Bs all have a unique charm. Whether it’s a picturesque garden or a beautiful breakfast room, the tiny details are what make bed and breakfasts a home away from home.
What are the best bed and breakfasts in Middlefield?
Below are some B&Bs in the area: The Cornell Inn, Lenox: 13.7 mi (22 km) from the downtown core. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. Situated 12.7 mi (20.5 km) from the heart of Middlefield. Enjoy the free full breakfast and deli. Shaker Mill Inn: 9 rooms. Located 18.1 mi (29.2 km) from the core of Middlefield.
What's the best time of year to stay at a B&B in Middlefield?
When you’re planning your escape to Middlefield, 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 27°F. The snowiest months in Middlefield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Middlefield?
When you want to explore some things to do in town, Skyline Trail and Fox Den Wildlife Management Area are some notable sights to visit. You might also consider a trip to sites like October Mountain State Forest or Jacob’s Pillow if you have time to see more of the area.
How can I get to and around Middlefield?
You can map out your trip in and around Middlefield ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 15.1 mi (24.3 km) from the city center. You can also search for flights into Westfield, MA (BAF-Barnes Municipal), which is 19.6 mi (31.6 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.