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A historic building with a clock, a flag, and a street lamp.

Book Pittsfield Bed & Breakfast

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    Check prices for these dates, December 13 – 14, 2026

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    Our top choices for Pittsfield bed & breakfast

    1. The Cornell Inn, Lenox & The Berkshires

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

    2. Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn".

    3. Inn at Silver Maple Farm

    A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

    4. The Inn at Stockbridge

    Front of property

    5. Chambery Inn

    A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

    6. The Trail in Adams - Berkshires’ Art Hotel

    A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.

    7. Devonfield Inn B&B

    A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

    8. Granville House

    A dining table with pastries, a coffee pot, and a vase of sunflowers.

    9. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    A two-story house with a brick entrance and a white facade.

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

    A neatly made bed with a textured white cover, a headboard, and two pillows, one of which is patterned. There is a small bedside table with a lamp and a painting of a landscape on the wall.

    11. Brook Farm Inn

    A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

    12. Experience Timeless Elegance in The Edith Wharton Room!

    A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

    13. Elegant Carriage House room with a queen bed and private patio.

    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.

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

    A porch with a white railing, a potted plant, and a view of a garden.

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

    A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

    A bedroom with a bed, a fireplace, a ceiling fan, and a door.

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

    A room with a sloped ceiling, a blue accent wall, a fireplace, a blue armchair, and a decorative plant arrangement.

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

    A bedroom with a bed, a bench, a door leading to an outdoor deck, and a wall-mounted air vent.

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

    A modern living room with a sofa, a coffee table, and a fireplace.

    20. Harbour House Inn

    A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

    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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    Learn more about Pittsfield

    Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

    See all hotels in Pittsfield

    A historic building with a clock, a flag, and a street lamp.

    Top reviews in Pittsfield

    Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn".

    Inn at Silver Maple Farm

    A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

    Brook Farm Inn

    A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

    The Cornell Inn, Lenox & The Berkshires

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

    The Inn at Stockbridge

    Front of property

    Chambery Inn

    A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

    Devonfield Inn B&B

    A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

    Harbour House Inn

    A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    A two-story house with a brick entrance and a white facade.

    The Trail in Adams - Berkshires’ Art Hotel

    A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.

    Frequently Asked Questions

    What is the nightly rate for a Bed and Breakfast in Pittsfield?

    Prices for B&Bs in Pittsfield often vary, but you can find a great deal from $159 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Pittsfield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

    When is the best time to book a B&B in Pittsfield?

    The best time to book a B&B in Pittsfield is during the vibrant summer months from June to August. This peak season invites outdoor enthusiasts eager to explore the scenic beauty of the Berkshires, with warm temperatures ranging from the mid-60s to mid-80s Fahrenheit. Visitors can enjoy an abundance of activities, from hiking in the lush forests to sailing on the pristine lakes, all while taking in the stunning landscapes that define this charming area.

    July is particularly popular, drawing travelers who appreciate a lively atmosphere. This month features numerous cultural events and festivals, including the renowned Tanglewood Music Festival, where you can enjoy world-class performances in a picturesque outdoor setting. The combination of warm weather and vibrant community activities makes this time ideal for those who thrive on social engagement and cultural experiences.

    For those considering a visit during a more budget-friendly time, October presents a fantastic option. During this month, the fall foliage reaches its peak, painting the landscape with vibrant hues of red, orange, and gold. The crisp air and beautiful scenery create a superb backdrop for leisurely walks and photo opportunities, all while avoiding the summer crowds.

    What is the difference between a Pittsfield Bed & Breakfast and a hotel?

    Every Pittsfield B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Pittsfield B&Bs.

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