A snow-covered forest with a stone bridge in the background.

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

Our top choices for Middlefield bed & breakfast

A snow-covered outdoor area with a patio, seating, and a covered dining area.

1. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

2. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
The price is AED 574
AED 949 total
includes taxes & fees
26 Oct - 27 Oct
The Red Door B&B
A red building with a sign reading "Shaker Mill Inn."

3. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 489
AED 536 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
A two-story building with a sign reading "Chambéry Inn".

4. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is AED 962
AED 1,074 total
includes taxes & fees
1 Nov - 2 Nov
Chambery Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AED 579
AED 646 total
includes taxes & fees
4 Oct - 5 Oct
Whistler's Inn Bed & Breakfast
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

6. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is AED 625
AED 699 total
includes taxes & fees
1 Nov - 2 Nov
The Trail in Adams - Berkshires’ Art Hotel
A dining table with pastries, a coffee pot, and a vase of sunflowers.

7. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AED 823
AED 919 total
includes taxes & fees
14 Oct - 15 Oct
Granville House
A large, two-story house with a well-maintained lawn and a fence.

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is AED 1,392
AED 1,555 total
includes taxes & fees
1 Nov - 2 Nov
Devonfield Inn B&B
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is AED 1,340
AED 1,571 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

10. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 909
AED 1,182 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

11. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AED 812
AED 937 total
includes taxes & fees
18 Oct - 19 Oct
Brook Farm Inn
A two-story house with a brick entrance and a white facade.

12. 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, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,403
AED 1,697 total
includes taxes & fees
1 Nov - 2 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

13. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,173
AED 1,522 total
includes taxes & fees
1 Nov - 2 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AED 997
AED 1,303 total
includes taxes & fees
1 Nov - 2 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

15. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is AED 1,438
AED 1,879 total
includes taxes & fees
1 Nov - 2 Nov
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

16. 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 AED 1,790
AED 2,324 total
includes taxes & fees
31 Oct - 1 Nov
Elegant Carriage House room with a queen bed and private patio.
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

17. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
A modern living room with a sofa, a coffee table, and a fireplace.

18. Elegant suite with a king bed, fireplace, and kitchenette.

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AED 1,731
AED 2,244 total
includes taxes & fees
1 Nov - 2 Nov
Elegant suite with a king bed, fireplace, and kitchenette.
A bedroom with a bed, a television, a fireplace, and a window.

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,555
AED 1,967 total
includes taxes & fees
1 Nov - 2 Nov
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A porch with a white railing, a potted plant, and a view of a garden.

20. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
Cozy Carriage House room with a double bed and private balcony
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 Middlefield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"So glad we stayed here! Our room was decorated like a 1940s Norman Rockwell painting, but had every modern comfort. We were in Stevens House, a half-block from the main inn - the shared living areas were like a home and our en-suite room was super nice. We had one dinner in the inn that was fancy, but we usually ate at other good restaurants & the patisserie within 1 block. Many fun shops, and a good laundromat also within 1 block."
Ruth 3-night trip
Posted 1 hour ago
The Red Lion Inn

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 well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 13.7 mi (22 km) from the heart of Middlefield. Enjoy the free full breakfast and unique décor. Shaker Mill Inn: 9 rooms. Situated 18.1 mi (29.2 km) from the heart of Middlefield. Chambery Inn: 9 rooms. Located 12.4 mi (20 km) from the core of Middlefield. Enjoy the private yard and deli.
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 Jacob's Pillow or Goose Pond Reservation 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.

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