Find hotels in Pittsfield, MA from ￥10,856

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 2 - Dec 3
Tomorrow
Dec 3 - Dec 4
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Filter by

Guest rating
Guest rating
Star rating

Compare 1,339 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥14,449
￥16,140 total
includes taxes & fees
Dec 16 - Dec 17
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (776)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ￥14,187
￥15,847 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (803)
"Clean room and staff was super friendly"
United States
Yuen
The price is ￥20,750
￥23,177 total
includes taxes & fees
Dec 22 - Dec 23
Hotel On North
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1004)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ￥14,542
￥16,243 total
includes taxes & fees
Dec 16 - Dec 17
Best Western Plus Berkshire Hills Inn & Suites
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is ￥17,298
￥19,322 total
includes taxes & fees
Dec 14 - Dec 15
Hilton Garden Inn Lenox Pittsfield
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ￥13,892
￥15,518 total
includes taxes & fees
Dec 3 - Dec 4
The Central Downtown Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
The price is ￥12,460
￥13,919 total
includes taxes & fees
Dec 16 - Dec 17
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (839)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ￥12,842
￥14,344 total
includes taxes & fees
Dec 8 - Dec 9
Berkshire Inn
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2159)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ￥12,683
￥15,873 total
includes taxes & fees
Dec 3 - Dec 4
Vacation Village in the Berkshires
Lobby
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
Castleton-on-Hudson
8.4 out of 10, Very Good, (1001)
"Room was spotless, staff very friendly."
United States
amber
The price is ￥15,095
￥16,756 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Comfort Inn & Suites East Greenbush - Albany
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1014)
"Great stay!"
United States
Ann
The price is ￥9,719
￥10,856 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ￥17,057
￥19,053 total
includes taxes & fees
Dec 8 - Dec 9
Berkshires Untold
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1006)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ￥15,267
￥17,053 total
includes taxes & fees
Dec 22 - Dec 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ￥22,116
￥30,809 total
includes taxes & fees
Dec 21 - Dec 22
The Cornell Inn, Lenox & The Berkshires
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
The price is ￥16,567
￥20,678 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1013)
"Staff was very nice!"
United States
David
The price is ￥16,660
￥18,610 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1004)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ￥25,188
￥35,112 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Red Lion Inn
Double Room | Egyptian cotton sheets, premium bedding, memory foam beds, desk
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.6 out of 10, Good, (117)
"Yes everything was perfect, just had a little trouble getting the WIFI for the TV set up! "
United States
Zenovia
The Brooks Motel
Suite, 2 Bedrooms | Frette Italian sheets, premium bedding, down comforters, minibar
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (444)
"It is the perfect place to stay!"
United States
Darrell
The price is ￥23,661
￥29,905 total
includes taxes & fees
Dec 9 - Dec 10
The Porches Inn at Mass MoCA
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.
View all properties

Great weekend hotel deals in Pittsfield, MA

Showing deals for:Dec 12 - Dec 14

Image gallery for Best Western Plus Berkshire Hills Inn & Suites

Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6/10Excellent (1,004 reviews)
Member Price available
Price is ￥15,431
￥34,472 total
includes taxes & fees
Sign in for Member Price
Best Western Plus Berkshire Hills Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Pittsfield attractions

Hardly anyone here! Great way to spend a week day, skiing and tubing!
Photo by Robin/Loving Life
Open Photo by Robin/Loving Life

Bousquet Ski Area

4.0/5 (23 reviews)
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.
See properties
Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres (12 km2) and the population rising to over 300.After reaching peak membership in the 1840s, the Shaker movement gradually dwindled, partially due to the urban migration that accompanied the Industrial Revolution, and by the westward migration of New England's youth. By the early twentieth century, the population of the village had fallen to around 50, most of whom were children. The remaining Shakers sold off their excess land, and many buildings were destroyed.The decision was eventually made in 1960 to close the village and sell the property and buildings. Non-Shakers were impressed by the Hancock Shaker property—scrupulously clean, neat, and well-tended—and their innovations in farming, such as the round barn that attracted much attention Visitors also praised Hancock Shakers' products, including boxes "of beautiful workmanship" and garden seeds. Before 1820, the village was prosperous and the Shakers were respected as good neighbors.
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Hancock Shaker Village

4.5/5 (73 reviews)
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
See properties

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
Pittsfield featuring a city

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Pittsfield

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY
The price is ￥15,095 per night from Jan 1 to Jan 2
￥15,095
￥16,756 total
Jan 1 - Jan 2, 2026
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)

Frequently asked questions

Where is the best place for a stay in Pittsfield?
Hotel On North is a favorite with Expedia customers. This hotel offers free parking and a bar. Other top choices based on traveler reviews include Holiday Inn Express & Suites Pittsfield - Berkshires by IHG and Hilton Garden Inn Lenox Pittsfield. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best vacation home rentals in Pittsfield?
Hancock Village Inn Near Jiminy Peak: This Pittsfield vacation home rental is located on a river and has a fireplace, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and a hot tub. Another good choice for your trip to Pittsfield is Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, you'll find most hotel reservations are refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
Where can I learn more about changing or cancelling my trip to Pittsfield?
For more details about changing or cancelling your trip to Pittsfield, head over to our customer service page.
What's the best accommodation for a budget-friendly stay in Pittsfield?
Based on our traveler reviews, Berkshire Inn is a top choice for a less expensive stay. View all budget hotels in Pittsfield.
What's the best hotel for a family vacation in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good choices for your kid-friendly vacation include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn Express & Suites Pittsfield - Berkshires by IHG. Attractions like Berkshire Museum and Bousquet Ski Area are also fun for kids of all ages. Find more child-friendly accommodations in Pittsfield.
What's the best LGBTQ-friendly place to stay in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top LGBTQ-friendly hotel, and features free WiFi and free internet. Hilton Garden Inn Lenox Pittsfield is another good option for your stay. See all available hotels listed as LGBTQ-friendly in Pittsfield.
What's the best pet-friendly hotel in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top dog-friendly hotel, and offers a restaurant along with free WiFi for its human guests. Other good choices for you and your pet include Hilton Garden Inn Lenox Pittsfield and Best Western Plus Berkshire Hills Inn & Suites. See more pet-friendly hotel accommodations in Pittsfield.
Where is the best hotel to stay near Hancock Shaker Village?
Best Western Plus Berkshire Hills Inn & Suites is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located 1.6 mi (2.6 km) from Hancock Shaker Village. Other good options within a few miles include Inn At Richmond and Yankee Inn.
What about the best place to stay close to Bousquet Ski Area?
One of the top choices for your stay is Hilton Garden Inn Lenox Pittsfield, located a short 1 mi (1.5 km) from Bousquet Ski Area, and this 3-star hotel offers a restaurant and an indoor pool. Berkshire Mountain Lodge, located just 0.8 mi (1.4 km) away, is another good choice for your stay.
What are some accommodations with pools in Pittsfield?
Hilton Garden Inn Lenox Pittsfield is a top hotel with a pool, free WiFi, and free parking. View all hotels with pools in Pittsfield.
What is the best accommodation for staying close to Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Pittsfield like?
Visitors to Pittsfield are sure to enjoy the sporting events, entertainment choices, and theaters. Tourists can also enjoy the city's museums, lake views, and ski areas. In Pittsfield, there are 74 hotels and other accommodations to choose from. Find out more about Pittsfield.
What is there to see in Pittsfield?
Cultural venues include Berkshire Museum, Colonial Theater, and Hancock Shaker Village. The picturesque setting of Housatonic River and Canoe Meadows Wildlife Sanctuary exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Bousquet Ski Area and Berkshire Athenaeum. Check out what more to see and do in Expedia's Pittsfield guide.
How can I get around Pittsfield?
To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. If you want to venture out around the area, you may want a rental car in Pittsfield for your journey.
What's the seasonal weather like in Pittsfield?
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 Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia