Photo by Elizabeth Massa Peroulakis

Search B&B in Middlefield

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Compare 28 B&B in Middlefield with updated reviews, rates, and availability.

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (561)
"Convient to town,clean rooms,nice breakfast,friendly staff,good parking,good value."
The price is AED 511
AED 570 total
includes taxes & fees
1 Jan - 2 January 2025
The Ellery

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1001)
"the staff was great. rooms where clean there is a bar on site & a bottle of red wine complimentary in the room. a lot in the area unfortunately it was too cold to enjoy a lot of of it"
The price is AED 448
AED 526 total
includes taxes & fees
12 Jan - 13 January 2025
The Cornell Inn, Lenox

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"We really enjoyed our stay. The breakfast was really good and the added touch of a welcome drink was really fun and made our stay feel special. We would like to come back again. "
The price is AED 463
AED 543 total
includes taxes & fees
29 Dec - 30 Dec
Lakehouse Inn

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (465)
"While we only stayed at The Old Mill for one night we enjoyed the handsome and very comfortable room (Waterfall) and the view of the waterfall and railroad bridge and would love to come back and stay longer - and try the breakfast choices (base on the aromas coming from the tavern in the morning). The staff was pleasant and helpful. "
The price is AED 860
AED 961 total
includes taxes & fees
26 Dec - 27 Dec
Old Mill Inn

Granville House

3.0 star property
10.0 out of 10, Exceptional, (78)
"Wonderful stay. Charming inn with a virtual library of books for every interest. Terrific breakfast. Will definitely return."
The price is AED 735
AED 821 total
includes taxes & fees
26 Dec - 27 Dec
Granville House

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (361)
"Everything was amazing. It was truly an experience. "
The price is AED 698
AED 779 total
includes taxes & fees
26 Dec - 27 Dec
Chambery Inn

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (404)
"Quaint "
The price is AED 386
AED 423 total
includes taxes & fees
5 Jan - 6 January 2025
Shaker Mill Inn

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (119)
"Great location "
The price is AED 1,098
AED 1,227 total
includes taxes & fees
6 Jan - 7 January 2025
Devonfield Inn B&B

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 1,337
AED 1,493 total
includes taxes & fees
20 Jan - 21 January 2025
33 Main

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
26 Dec - 27 Dec
Tanglewood Suites

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (125)
"Stayed only one night Very cosy, quiet place "
The price is AED 592
AED 662 total
includes taxes & fees
2 Jan - 3 January 2025
The Trail in Adams - Berkshires’ Art Hotel

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 841
AED 940 total
includes taxes & fees
7 Jan - 8 January 2025
Brook Farm Inn

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...
Whistler's Inn Bed & Breakfast

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 1,559
AED 1,885 total
includes taxes & fees
1 Jan - 2 January 2025
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
26 Dec - 27 Dec
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
26 Dec - 27 Dec
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! "
The price is AED 1,561
AED 1,712 total
includes taxes & fees
3 Jan - 4 January 2025
Inn at Kenmore Hall

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 944
AED 998 total
includes taxes & fees
26 Dec - 27 Dec
Harbour House Inn

Romantic Boutique Hotel / B&B - Deluxe Firespa Suite

10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
5 Jan - 6 January 2025
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
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, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
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 Chester Town Hall or October Mountain State Forest 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.