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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Middlefield bed & breakfast

Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels
Old Mill Inn

Old Mill Inn

3.0 star property
Hatfield
9.4 out of 10, Exceptional, (500)
"Loved our stay! "
United States
Jay
Old Mill Inn
Terrace/patio
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, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is AED 638
AED 713 total
includes taxes & fees
11 Dec - 12 Dec
The Trail in Adams - Berkshires’ Art Hotel
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 AED 396
AED 435 total
includes taxes & fees
14 Dec - 15 Dec
Shaker Mill Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 684
AED 802 total
includes taxes & fees
12 Dec - 13 Dec
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
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
The price is AED 731
AED 816 total
includes taxes & fees
12 Dec - 13 Dec
Granville House
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 AED 921
AED 1,080 total
includes taxes & fees
1 Jan - 2 January 2026
The Inn at Stockbridge
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 AED 1,602
AED 1,789 total
includes taxes & fees
7 Jan - 8 January 2026
33 Main
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
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 AED 804
AED 804 total
includes taxes & fees
11 Dec - 12 Dec
Tanglewood Suites
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AED 790
AED 835 total
includes taxes & fees
7 Jan - 8 January 2026
Harbour House Inn
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 AED 995
AED 1,301 total
includes taxes & fees
11 Dec - 12 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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 AED 1,403
AED 1,697 total
includes taxes & fees
7 Jan - 8 January 2026
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 AED 995
AED 1,301 total
includes taxes & fees
11 Dec - 12 Dec
Experience Timeless Elegance in The Edith Wharton Room!
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 AED 1,116
AED 1,461 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Carriage House room with a double bed and private balcony
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
18 Dec - 19 Dec
Inn at Kenmore Hall
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 AED 1,055
AED 1,379 total
includes taxes & fees
11 Dec - 12 Dec
Elegant Carriage House room with a queen bed and private patio.
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is AED 1,177
AED 1,538 total
includes taxes & fees
14 Dec - 15 Dec
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
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 1,449
AED 1,896 total
includes taxes & fees
14 Dec - 15 Dec
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
The price is AED 1,570
AED 2,005 total
includes taxes & fees
11 Dec - 12 Dec
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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. Chambery Inn: 9 rooms. 12.4 mi (20 km) from the downtown core. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. Situated 18.1 mi (29.2 km) from the heart of Middlefield. Brook Farm Inn: 15 rooms. 14 mi (22.5 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Lakehouse Inn: 14 rooms. Located 12.7 mi (20.5 km) from the core of Middlefield. Enjoy the free full breakfast 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.