This Pittsfield guesthouse is situated in a peaceful Berkshires neighbourhood, within a short walking distance (less than 1km) of both Onota Lake and Pittsfield's town centre. Offering a private queen-sized room with a mini-fridge, this self-catering unit sleeps two guests and includes access to a shared kitchen, bathroom, garden, and off-street parking; responsive hosts are available via app.
Pittsfield, MA
06/09 – 13/09
A$920/nighttotal: A$6440 (7 )
Experience Timeless Elegance In The Edith Wharton Room!
1 2
B&B , Lenox
This Lenox guesthouse is conveniently located near Kennedy Park (1.6 km), Stockbridge Bowl (4.5 km), and The Bookstore (0.96 km), offering easy access to outdoor recreation and cultural attractions. The 11-square-metre (118 sq ft) single-bedroom, single-bathroom guest house sleeps three and includes amenities such as a coffee maker, kettle, and air conditioning; linens and towels are provided.
9.8 280 reviews
Pittsfield, MA
13/10 – 25/10
A$221/nighttotal: A$2652 (12 )
Berkshire Village Carriage House - Super Private!!
1 2
B&B , Lanesborough
This one-bedroom house is situated in the mountains near Lanesborough, just 10km from both the Crane Museum of Papermaking and Mount Greylock State Reservation. The 46 square metre property offers a terrace, garden, and parking, and is ideal for a couple seeking a peaceful retreat with modern amenities including a fully equipped kitchen, Wi-Fi, and air conditioning.
Pittsfield, MA
30/06 – 31/10
A$1326/nighttotal: A$163098 (123 )
100 Yr Berkshire Mansion King Rm W Marble Bathroom
1 1
B&B , Lenox
This charming bed and breakfast is situated in Lenox, just a short distance from the town centre and within easy reach of attractions like Tanglewood and the Norman Rockwell Museum. The surrounding area offers a peaceful retreat from the hustle and bustle of town, while still being close to all the amenities Lenox has to offer. The B&B has one bedroom and one bathroom, comfortably accommodating up to two guests. Guests can enjoy a range of amenities, including a shared library, a communal dining area, a private kitchen, a garden, a sauna, and parking.
9.8 108 reviews
Pittsfield, MA
13/10 – 25/10
A$188/nighttotal: A$2256 (12 )
Newly Renovated
Red Door Annex
1 2
B&B , Pittsfield
The Red Door Annex, a self-contained apartment in Pittsfield, Massachusetts, enjoys a central Berkshire County location equidistant between Great Barrington and Williamstown/North Adams, placing it within a 32km radius of Lenox and Tanglewood. This one-bedroom apartment, sleeping two, offers a queen-sized bed, private keypad entry, parking for two cars, a kitchenette with a microwave and toaster oven, a private deck with a hammock and fire pit, and is close to hiking trails and the rail trail.
9.0 43 reviews
Pittsfield, MA
12/07 – 18/07
A$134/nighttotal: A$804 (6 )
Room #3: Twin Size Bed
1 2
B&B , Pittsfield
This Pittsfield guesthouse is ideally situated a short walk from Onota Lake and the town centre, with Tanglewood approximately 32km away by car and Balderdash Cellar just 16km. The self-catering room, sleeping up to two guests, offers a private room with air conditioning, a shared kitchen and bathroom, and parking; nearby hiking trails and a convenience store add further convenience.
Pittsfield, MA
12/07 – 18/07
A$349/nighttotal: A$2094 (6 )
The Central Downtown Inn&suites
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B&B , Pittsfield
This Pittsfield guesthouse offers five spacious condo-style suites, each with a private deck, full kitchen (fridge, microwave, dishwasher), and en-suite bathroom, sleeping up to four guests; precise location within Pittsfield and proximity to local attractions requires further clarification. Each suite provides a living room, bedroom, and a full kitchen, allowing self-catering and boasting pet-friendly accommodation with Wi-Fi, air conditioning, and on-site parking.
Pittsfield, MA
21/08 – 24/08
A$1347/nighttotal: A$4041 (3 )
Retreat Room In Motel Like Build
1 6
B&B , Lenox
This Lenox B&B, sleeping up to 16 guests, offers stunning views of the Berkshire landscape; its precise location within Lenox is unspecified, but the emphasis on scenic overlooks suggests a position offering panoramic vistas. The guesthouse features one bathroom, air conditioning, parking, and internet access; further details regarding the property's size and specific layout are unavailable.
8.0 647 reviews
Pittsfield, MA
06/09 – 13/09
A$435/nighttotal: A$3045 (7 )
Whistler's Inn
1 2
B&B , Lenox
The Whistler's Inn is a charming bed and breakfast situated in Lenox, Massachusetts, a short distance from Tanglewood Musical Center and Shakespeare & Company Theater. The inn has consistently received very good user ratings for its cleanliness and excellent location. Each room at the inn has a unique style and features a private bathroom. Guests can enjoy a daily gourmet breakfast, afternoon tea and cookies, and have access to a parlour room with a piano and a library. The inn also has a garden and a terrace, and guests can enjoy free Wi-Fi and parking.
Pittsfield, MA
12/07 – 18/07
A$349/nighttotal: A$2094 (6 )
Home A While
1 2
B&B , Pittsfield
This Pittsfield guesthouse, perfect for a Berkshire County getaway, offers a convenient base for exploring local attractions such as the Berkshire Museum and Barrington Stage Company, though precise distances aren't specified. Sleeping up to three guests, this one-bedroom, one-bathroom lodging boasts a well-equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, parking, and internet access; pets are welcome.
Pittsfield, MA
30/06 – 31/10
A$454/nighttotal: A$55842 (123 )
New,cozy Bed & Bath Only, Village Lenox Location!
1 1
B&B , Lenox
This Lenox apartment is situated in a historic district, within walking distance of the village's shops and restaurants. The self-catering studio flat offers a Murphy bed, en-suite bathroom, in-room coffeemaker and small refrigerator, sleeping up to two guests, and boasts access to a swimming pool and garden (completion expected Summer).
8.6 367 reviews
Pittsfield, MA
13/10 – 25/10
A$221/nighttotal: A$2652 (12 )
The Central Downtown Inn & Suites
1 2
B&B , Pittsfield
This guesthouse is conveniently located in Pittsfield, just 0.3 kilometres from the Berkshire Museum and within easy reach of Bousquet Ski Area and Hancock Shaker Village. It is rated very good by previous guests. The guesthouse offers a kitchen with a freezer, microwave oven, and dishwasher, as well as air conditioning, a terrace, and parking. Guests can enjoy free Wi-Fi, laundry facilities, and express check-in and check-out.
Best Pittsfield, MA bed and breakfasts with breakfast included
9.1 1529 reviews
Pittsfield, MA
06/09 – 13/09
A$525/nighttotal: A$3675 (7 )
The Cornell Inn, Lenox & The Berkshires
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B&B , Lenox
This charming bed and breakfast is situated in Lenox, just a short distance from the Boston Symphony Orchestra's Tanglewood Institute, and within easy reach of the town's restaurants. It boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay. The guest house is set on four acres, offering a peaceful and secluded environment. Guests can enjoy a gourmet breakfast, relax on the private deck, or explore the gardens that connect to Kennedy Park.
Pittsfield, MA
12/07 – 18/07
A$528/nighttotal: A$3168 (6 )
Eastgate Inn B&b
1 2
B&B , Lenox
Eastgate Inn is a charming bed and breakfast located in Lenox, a short walk from the city centre and just a few kilometres from Tanglewood Music Centre, Frelinghuysen Morris House and Studio, and Lenox Library. The inn offers a peaceful and relaxing atmosphere, ideal for those seeking a tranquil escape from the hustle and bustle. The Eastgate Inn features a comfortable and inviting common area with a library for quiet reading and a barbecue area for outdoor gatherings. Guests can enjoy free Wi-Fi and parking, as well as a flexible check-in process and personalised service from the friendly staff.
Pittsfield, MA
03/07 – 06/07
A$1572/nighttotal: A$4716 (3 )
The Cornell Inn, Lenox & The Berkshires
1 2
B&B , Lenox
The Cornell Inn is a charming bed and breakfast situated in Lenox, just a short walk from the town centre and close to attractions like The Bookstore, Lenox Library, and Ventfort Hall Mansion. It enjoys a peaceful location, ideal for exploring the area's history and culture. The inn offers a range of rooms, all equipped with modern amenities, including a microwave oven, air conditioning, and a private bathroom. Guests can enjoy a range of facilities, including a restaurant, a bar, a terrace, a garden, and free parking.
Best Pittsfield, MA bed and breakfasts with a garden
Pittsfield, MA
30/06 – 31/10
A$582/nighttotal: A$71586 (123 )
Mansion King Bedroom W View & Huge Marble Bathroom
1 1
B&B , Lenox
This Lenox guesthouse offers two bedrooms and one bathroom, sleeping up to four guests, and includes a fridge, air conditioning, garden, and parking. The property boasts internet access and is conveniently located in Lenox, though its precise address and proximity to specific landmarks remain unspecified.
Pittsfield, MA
12/07 – 18/07
A$349/nighttotal: A$2094 (6 )
The Central Downtown Inn
1 2
B&B , Pittsfield
The Central Downtown Inn & Suites is a five-bedroom guesthouse located in central Pittsfield, offering easy access to the Berkshire Museum and Pittsfield Public Library, with distances to these attractions needing clarification. This pet-friendly inn boasts five bathrooms, sleeps ten guests, includes a kitchen with fridge, microwave, and dishwasher, and provides air conditioning, internet access, parking, and a garden.
Pittsfield, MA
30/06 – 31/10
A$15935/nighttotal: A$1960005 (123 )
Terrace Suite In Five-star Hotel
1 1
B&B , Stockbridge
This Stockbridge guesthouse offers a ground-floor suite with mountain views, a 40-foot private covered terrace, and is situated a short drive from Stockbridge's attractions, the precise location unspecified. The self-catering unit features a king-size bed, a BeoVision 7-40 entertainment system, an antique soaking tub, and a large shower, accommodating up to two guests.
9.6 455 reviews
Pittsfield, MA
03/07 – 06/07
A$1165/nighttotal: A$3495 (3 )
Chambery Inn
1 2
B&B , Lee
The Chambery Inn is situated in Lee, Massachusetts, a short drive from both the Berkshire Scenic Railroad Museum and Tanglewood Musical Center, making it an ideal base for exploring the area's attractions. The inn has consistently received excellent ratings for its location, cleanliness, and overall experience. This former schoolhouse has been transformed into a charming guesthouse with a unique design, featuring individual room styles and special features. Guests can enjoy a continental breakfast delivered to their room, relax in the garden, take advantage of the spa, and enjoy the nearby Ski Butternut resort for winter sports.
Frequently asked questions about bed and breakfast in Pittsfield, MA
What is the typical weather in Pittsfield, MA, and how does it affect outdoor plans?
Pittsfield has four distinct seasons. Summers are warm and humid, perfect for enjoying outdoor activities like hiking and picnicking. Winters are cold and snowy, so be sure to pack warm clothes if you're visiting then. Spring and autumn are mild and beautiful, ideal for exploring the city's parks and gardens.
What are the best bed and breakfasts in Pittsfield, MA?
What are the best cultural activities and events in and around Pittsfield, MA?
Pittsfield is known for its vibrant arts scene. The Barrington Stage Company, a renowned theatre, hosts a variety of productions throughout the year. The Clark Art Institute, just a short drive away, boasts an impressive collection of art and beautiful gardens. You can also catch a performance at the Colonial Theatre, a historic venue that has hosted many famous artists.
What are the best bed and breakfasts with a pool in Pittsfield, MA?
Which hiking trails are recommended for exploring in and around Pittsfield, MA?
For a moderate hike, try the scenic Taconic Crest Trail, offering stunning views of the surrounding mountains. The more challenging Mount Greylock Trail, leading to the highest peak in Massachusetts, is perfect for experienced hikers. If you're looking for a shorter walk, the Bartholomew's Cobble Nature Preserve offers beautiful woodland scenery.
What are the best bed and breakfasts with a jacuzzi in Pittsfield, MA?
What amenities are commonly offered in bed and breakfasts in Pittsfield, MA?
Most bed and breakfasts in Pittsfield offer a range of amenities, including a hearty breakfast, comfortable rooms, and often a shared living area. Many also provide free Wi-Fi, parking, and laundry facilities, making them a convenient and comfortable option for travellers.
What are the best bed and breakfasts for families and kids in Pittsfield, MA?
Best Pittsfield, MA bed and breakfasts with parking
8.6 367 reviews
Pittsfield, MA
13/10 – 25/10
A$221/nighttotal: A$2652 (12 )
The Central Downtown Inn & Suites
1 2
B&B , Pittsfield
This guesthouse is conveniently located in Pittsfield, just 0.3 kilometres from the Berkshire Museum and within easy reach of Bousquet Ski Area and Hancock Shaker Village. It is rated very good by previous guests. The guesthouse offers a kitchen with a freezer, microwave oven, and dishwasher, as well as air conditioning, a terrace, and parking. Guests can enjoy free Wi-Fi, laundry facilities, and express check-in and check-out.
9.8 280 reviews
Pittsfield, MA
13/10 – 25/10
A$221/nighttotal: A$2652 (12 )
Berkshire Village Carriage House - Super Private!!
1 2
B&B , Lanesborough
This one-bedroom house is situated in the mountains near Lanesborough, just 10km from both the Crane Museum of Papermaking and Mount Greylock State Reservation. The 46 square metre property offers a terrace, garden, and parking, and is ideal for a couple seeking a peaceful retreat with modern amenities including a fully equipped kitchen, Wi-Fi, and air conditioning.
Pittsfield, MA
12/07 – 18/07
A$528/nighttotal: A$3168 (6 )
Eastgate Inn B&b
1 2
B&B , Lenox
Eastgate Inn is a charming bed and breakfast located in Lenox, a short walk from the city centre and just a few kilometres from Tanglewood Music Centre, Frelinghuysen Morris House and Studio, and Lenox Library. The inn offers a peaceful and relaxing atmosphere, ideal for those seeking a tranquil escape from the hustle and bustle. The Eastgate Inn features a comfortable and inviting common area with a library for quiet reading and a barbecue area for outdoor gatherings. Guests can enjoy free Wi-Fi and parking, as well as a flexible check-in process and personalised service from the friendly staff.
Pittsfield, MA
03/07 – 06/07
A$1572/nighttotal: A$4716 (3 )
The Cornell Inn, Lenox & The Berkshires
1 2
B&B , Lenox
The Cornell Inn is a charming bed and breakfast situated in Lenox, just a short walk from the town centre and close to attractions like The Bookstore, Lenox Library, and Ventfort Hall Mansion. It enjoys a peaceful location, ideal for exploring the area's history and culture. The inn offers a range of rooms, all equipped with modern amenities, including a microwave oven, air conditioning, and a private bathroom. Guests can enjoy a range of facilities, including a restaurant, a bar, a terrace, a garden, and free parking.
Best Pittsfield, MA bed and breakfasts with air conditioning
Pittsfield, MA
30/06 – 31/10
A$15935/nighttotal: A$1960005 (123 )
Superior Room In Five-star Hotel
1 1
B&B , Stockbridge
This Stockbridge guesthouse offers a queen-sized bed, private shower/tub, and either a courtyard or side view, but its precise location within Stockbridge and proximity to attractions like the Norman Rockwell Museum or Berkshire Theatre Festival requires further clarification. The single-bedroom, en-suite guest house sleeps two, features air conditioning, valet parking, and internet access; details regarding breakfast provision and common areas remain unspecified.
Pittsfield, MA
06/09 – 13/09
A$1271/nighttotal: A$8897 (7 )
Elegant Suite With A King Bed, Fireplace, And Kitchenette.
1 2
B&B , Lenox
This Lenox guesthouse is conveniently located within a 1.9km walk of both The Bookstore and Lenox Library. The 20-square-metre property offers one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with refrigerator and coffee maker.
Pittsfield, MA
30/06 – 31/10
A$15935/nighttotal: A$1960005 (123 )
Deluxe Room In Five-star Hotel
1 1
B&B , Stockbridge
This Stockbridge guesthouse is centrally located, offering easy walking access to Stockbridge's shops, restaurants, and cultural attractions. The one-bedroom, one-bathroom guest house sleeps two, featuring a king-size bed, air conditioning, valet parking, and a private courtyard or side view.
Pittsfield, MA
06/09 – 13/09
A$1129/nighttotal: A$7903 (7 )
Experience Timeless Elegance In The Niles Johnson Room At The Cornell Inn
1 2
B&B , Lenox
This Lenox guesthouse is conveniently located near Lenox Library and The Bookstore, a 1.9km stroll away. The 20 square metre room, sleeping up to three guests, features a fireplace, air conditioning, and is close to the Berkshire Scenic Railway Museum, Pleasant Valley Wilderness Sanctuary, and Tanglewood.