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Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sep - 13 Sep
In two months
9 Oct - 11 Oct

Our top choices for Middlefield bed & breakfast

Exterior

1. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (529 reviews)
"A perfect stay. Gorgeous location and setting. Immaculate property, beautiful rooms & inn. Priscilla is an absolute gem. She adds such a personal touch and I really enjoyed her presence. I felt welcome, safe & relaxed from start to finish. Can’t wait to return for a longer visit!"
United States
Ann
The price is AED 659
AED 736 total
includes taxes & fees
14 Sep - 15 Sep
Old Mill Inn
Terrace/patio

2. 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, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is AED 762
AED 851 total
includes taxes & fees
15 Sep - 16 Sep
The Trail in Adams - Berkshires’ Art Hotel
Front of property

3. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (384 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is AED 992
AED 1,108 total
includes taxes & fees
17 Aug - 18 Aug
Chambery Inn
Front of property - evening/night

4. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is AED 1,429
AED 1,596 total
includes taxes & fees
3 Sep - 4 Sep
Devonfield Inn B&B
Property grounds

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (513 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AED 585
AED 654 total
includes taxes & fees
1 Sep - 2 Sep
Whistler's Inn Bed & Breakfast
Front of property

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (101 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is AED 1,385
AED 1,624 total
includes taxes & fees
13 Sep - 14 Sep
The Inn at Stockbridge
Garden

7. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (466 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 680
AED 746 total
includes taxes & fees
8 Sep - 9 Sep
Shaker Mill Inn
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

8. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (105 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 1,010
AED 1,128 total
includes taxes & fees
17 Aug - 18 Aug
Granville House
Suite, Private Bathroom (RedBird Suite) | View from room

9. 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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,213
AED 1,467 total
includes taxes & fees
31 Aug - 1 Sep
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets

10. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 1,144
AED 1,496 total
includes taxes & fees
25 Aug - 26 Aug
Experience Timeless Elegance in The Edith Wharton Room!
Exterior

11. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 885
AED 936 total
includes taxes & fees
16 Sep - 17 Sep
Harbour House Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

12. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is AED 2,361
AED 2,637 total
includes taxes & fees
31 Aug - 1 Sep
33 Main
Interior

13. 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 1,232
AED 1,610 total
includes taxes & fees
8 Sep - 9 Sep
Elegant Carriage House room with a queen bed and private patio.
3 bedrooms, bed sheets

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 1,144
AED 1,496 total
includes taxes & fees
25 Aug - 26 Aug
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,320
AED 1,727 total
includes taxes & fees
31 Aug - 1 Sep
Historic Susan B. Anthony Room - Cozy & Charming Stay
Interior

16. 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 1,261
AED 1,648 total
includes taxes & fees
31 Aug - 1 Sep
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,702
AED 2,160 total
includes taxes & fees
26 Aug - 27 Aug
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Fireplace

18. 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
The price is AED 1,878
AED 2,454 total
includes taxes & fees
25 Aug - 26 Aug
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AED 1,878
AED 2,454 total
includes taxes & fees
25 Aug - 26 Aug
Elegant suite with a king bed, fireplace, and kitchenette.
1 bedroom, bed sheets

20. 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 1,584
AED 2,072 total
includes taxes & fees
31 Aug - 1 Sep
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Staff was wonderful and welcoming. Room was clean but rug was stained. There was no decaf coffee at breakfast. We would definitely stay there again"
Janet 1-night trip
Posted 3 hours ago
Quality Inn Great Barrington

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. Situated 12.4 mi (20 km) from the heart of Middlefield. Enjoy the private yard 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 Chesterfield Gorge 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.

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