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Compare 1,357 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is CA $208
CA $233 total
includes taxes & fees
Jul 17 - Jul 18
Holiday Inn Express & Suites Pittsfield - Berkshires

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is CA $259
CA $289 total
includes taxes & fees
Jul 21 - Jul 22
Hotel On North

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is CA $295
CA $329 total
includes taxes & fees
Jul 27 - Jul 28
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (513)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
The price is CA $122
CA $167 total
includes taxes & fees
Jul 15 - Jul 16
Berkshire Mountain Lodge

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"Very nice stay"
The price is CA $173
CA $194 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Plus Berkshire Hills Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (297)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is CA $163
CA $182 total
includes taxes & fees
Jul 15 - Jul 16
The Central Downtown Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is CA $157
CA $176 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (779)
"The motel was nicely done and clean. The beds were comfortable "
The price is CA $126
CA $141 total
includes taxes & fees
Jul 20 - Jul 21
Berkshire Inn

FairBridge Inn Express

2.5 star property
5.4 out of 10, (740)
"A total dump !"
The price is CA $97
CA $109 total
includes taxes & fees
Jul 15 - Jul 16
FairBridge Inn Express

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (552)
"Very clean and very nice staff. Breakfast was great"
The price is CA $228
CA $255 total
includes taxes & fees
Jul 15 - Jul 16
Berkshire Valley Inn

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (175)
"Lovely stay!"
The price is CA $288
CA $304 total
includes taxes & fees
Jul 15 - Jul 16
Blue Vista Motor Lodge

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (565)
"The staff, room and property was wonderful! "
The price is CA $171
CA $191 total
includes taxes & fees
Jul 15 - Jul 16
Maple Terrace Motel

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful location!"
The price is CA $231
CA $258 total
includes taxes & fees
Jul 15 - Jul 16
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (512)
"Hotel was clean and facilities were maintained. Best part was that you are permitted to use amenities at The Red Lion Inn down the road. "
The price is CA $219
CA $245 total
includes taxes & fees
Jul 15 - Jul 16
The Little Lion

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (834)
"Very, very clean with friendly owners. Located within a few minutes' drive of good restaurants and outdoor recreation areas. We would definitely stay again!"
The price is CA $131
CA $154 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Corner Motel

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (947)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is CA $221
CA $246 total
includes taxes & fees
Jul 15 - Jul 16
Jiminy Peak Mountain Resort

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (252)
"Lovely hotel in the heart of Lenox. The rooms and property were very nice. The staff was great. We would definitely stay here again!"
The price is CA $266
CA $297 total
includes taxes & fees
Jul 15 - Jul 16
The Whitlock

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"Friendly staff, easy parking"
The price is CA $173
CA $194 total
includes taxes & fees
Jul 28 - Jul 29
Quality Inn

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1875)
"Very nice places "
The price is CA $110
CA $137 total
includes taxes & fees
Jul 15 - Jul 16
Vacation Village in the Berkshires

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (927)
"Clean, conscientious service, great breakast spread. "
The price is CA $159
CA $178 total
includes taxes & fees
Jul 15 - Jul 16
Willows Motel Williamstown
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

Come to Pittsfield and enjoy its baseball, entertainment, and opera.

Pittsfield showing a city

Find out more about Pittsfield

Find out more about Pittsfield

Top reasons to visit Pittsfield

  • Outdoor Adventures: Enjoy skiing at local resorts and hiking through scenic trails, perfect for adventure seekers.
  • Cultural Experiences: Explore historic houses and vibrant downtown attractions that showcase local culture.
  • Beautiful Nature Reserves: Discover stunning landscapes in Western Massachusetts, ideal for relaxation and exploration.
  • Diverse Accommodation: Choose from charming inns to luxurious hotels that cater to every traveller's needs.
  • Family-Friendly Atmosphere: Pittsfield offers a welcoming environment with activities for all ages.

Find great hotels in Pittsfield

Pittsfield, Massachusetts, presents an impressive selection of accommodation options that cater to every traveller's needs, from budget-friendly inns to luxurious four-star hotels. Whether you're seeking a charming bed and breakfast or a modern hotel with pet-friendly amenities, you'll find the perfect fit for your adventure or business trip. Explore the best hotels and suites in Pittsfield for a memorable stay in this vibrant city.

  • The Yankee, Trademark Collection by Wyndham: Located 4.8km from Pittsfield, The Yankee is a premier destination for business travellers seeking a blend of comfort and efficiency. This hotel features state-of-the-art amenities, including a 24-hour Business Centre, multiple meeting rooms, and flexible conference spaces tailored for corporate events. With a focus on providing a productive environment, The Yankee ensures guests have all the necessary resources at their fingertips, making it an ideal choice for those on a professional journey.
  • Holiday Inn & Suites Pittsfield-Berkshires by IHG: Situated in the heart of Pittsfield, this family-friendly hotel embraces adventure and exploration. Guests can partake in numerous outdoor activities, such as nearby horseback riding, cross-country skiing, and hiking trails. The hotel is equipped with child-friendly amenities, including free cribs and window guards, making it perfect for families. Additionally, it welcomes pets, allowing for a complete family experience. The Holiday Inn & Suites combines comfort with the thrill of adventure, ensuring an unforgettable stay.
  • Best Western Plus Berkshire Hills Inn & Suites: Nestled in Pittsfield, this versatile hotel caters to families, business travellers, and pet owners alike. With a 24-hour Business Centre, meeting rooms, and conference spaces, it supports professional needs while also providing amenities for children, like a games area and first aid kits. Pet-friendly policies, including a designated dog exercise area, make it easy for guests to travel with their furry companions. The Best Western Plus offers a well-rounded experience for a diverse range of visitors.

Where to stay in Pittsfield

Pittsfield, Massachusetts, offers a delightful blend of adventure and relaxation, perfect for Canadian tourists seeking a diverse vacation. Explore the vibrant downtown, where family-friendly attractions and local shops await. Venture into the scenic landscapes of Western Massachusetts for skiing and outdoor fun, or enjoy romantic strolls through charming neighborhoods. Whether you’re seeking history or modern vibes, Pittsfield provides an unforgettable experience in a picturesque setting.

  • Lenox: Nestled 11.3km from Pittsfield, Lenox is a charming destination known for its vibrant arts scene and outdoor activities. The town comes alive from June to August, attracting visitors seeking entertainment, romance, and family experiences. Enjoy music concerts and theatre performances, or hit the nearby ski slopes in winter. Nature enthusiasts will appreciate the stunning lakes and mountains, making Lenox an ideal spot for relaxation and adventure alike. Don’t miss the local event conference venues that host a variety of gatherings throughout the year.
  • Stockbridge: Located 19.3km away from Pittsfield, Stockbridge is a cultural gem that beckons travellers year-round. With peak visitor numbers from July to September, this town is rich in history and art. Stockbridge offers a delightful mix of culture, romance, and entertainment, with music concerts and theatre performances to enjoy. Explore the local landmarks, including a beautiful lake, a historic monument, and the peaceful shrine nearby. Stockbridge's unique charm provides a perfect backdrop for leisurely strolls and memorable experiences.
  • Hancock: Just 11.3km from Pittsfield, Hancock is a haven for outdoor enthusiasts and adventure seekers. The town sees an influx of visitors primarily in March to April and during the summer months. Renowned for its exceptional skiing opportunities, Hancock boasts top-notch ski fields and resorts, drawing sports lovers and thrill-seekers. With its picturesque mountains and serene lakes, this destination offers breathtaking views and ample opportunities for outdoor recreation, making it a must-visit for those looking to embrace the great outdoors.

Things to do in Pittsfield

Pittsfield, Massachusetts, offers a fantastic range of activities for adventure seekers and sports enthusiasts, making it an ideal vacation destination. You can enjoy skiing at local resorts, explore convenient hiking trails, and partake in daily tours. Additionally, consider indulging in a wellness retreat to unwind after your outdoor adventures. With its blend of outdoor excitement and relaxation, Pittsfield is perfect for a memorable getaway.

Shopping

Pittsfield offers charming shopping experiences like Guido's Marketplace, a vibrant public market. The Bookstore is only 9.7km away, perfect for book lovers. If you're up for a drive, visit Berkshire Mountain Country Store, located 16.1km from Pittsfield, for unique gifts and souvenirs.

Recreation

Tanglewood Music Center offers an enchanting concert experience amidst nature, perfect for music lovers. Skyline Country Club invites you to enjoy a round of golf while soaking in the beautiful outdoors. For relaxation, Kennedy Park provides a tranquil setting for leisurely walks and rejuvenation in nature.

Adventure

Experience thrilling adventures at Jiminy Peak Mountain Resort, a ski field 12.9km from Pittsfield, perfect for skiing enthusiasts. For hiking lovers, the Skyline Trail offers breathtaking scenery 20.9km away, while Bousquet Ski Area, located within Pittsfield, delivers an exhilarating ski experience amid sports vibes.

Nightlife

Pittsfield's nightlife offers cultural experiences at the Colonial Theater and Barrington Stage Company, both brimming with family-friendly entertainment and romance. Just a short drive away, Shakespeare and Company adds to the vibrant scene, making for a captivating evening filled with art and performance.

Booking tips and Expedia advantages for Pittsfield

When planning your trip to Pittsfield, Massachusetts, consider visiting popular free attractions like the National Shrine of the Divine Mercy and Lee Premium Outlets. For transport, buses are a cost-effective option. Aim to visit during the cheaper months of March to April or November, and try to book your stay for a Tuesday to save money. Use Expedia to find great hotel deals by combining your hotel, flights, and activities, and always sort by price to discover the best offers. This way, you can enjoy your vacation without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Pittsfield are March to April and November, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Pittsfield is Tuesday. The most expensive day to stay in Pittsfield is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, such as your budget, preferred location, and the type of hotel you're looking for. To discover the most affordable prices and special offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save some money by combining your hotel stay in Pittsfield with your flights and activities through an Expedia package.

Find the best attractions in Pittsfield

Pittsfield, Massachusetts, is a fantastic destination for Canadian tourists seeking adventure and culture. With its stunning mountains, historic houses, and beautiful nature reserves, you can enjoy a variety of outdoor activities and sports. Whether you're hitting the slopes or exploring local history, Pittsfield offers a blend of experiences that cater to both adventure seekers and culture enthusiasts alike.

  • Hancock Shaker Village: Experience the tranquility of this historic village, showcasing Shaker culture through beautifully preserved buildings, gardens, and interactive exhibits. It's a serene spot where you can learn about the unique communal lifestyle and craftsmanship of the Shakers.
  • National Shrine of the Divine Mercy: Located 17.7km from Pittsfield, this shrine offers a peaceful environment for reflection and spiritual growth. Visitors can explore stunning architecture, serene gardens, and attend services that celebrate Divine Mercy.
  • Berkshire Museum: Situated in Pittsfield, this natural history museum combines culture and family fun. It features diverse exhibits on art, science, and history, along with an aquarium, making it a fantastic destination for visitors of all ages.

Best time to go to Pittsfield

Visitor numbers in Pittsfield is generally unchanged in popularity throughout the year. The best time to visit Pittsfield can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pittsfield falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Pittsfield falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.6°F (-5.2°C)Light RainMostly CloudyAverageAverage
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.4°F (0.2°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October50.0°F (10.0°C)Light RainMostly SunnySlightly LowSlightly High
November37.6°F (3.1°C)Light RainMostly SunnySlightly LowSlightly Low
December29.3°F (-1.5°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Pittsfield

When visiting Pittsfield, Massachusetts, you can fly into three major airports. Hartford, CT (BDL-Bradley Intl.) is located 74.0km away, with nearby hotels such as the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Albany, NY (ALB-Albany Intl.) is 56.3km away, with great options like The Landing Hotel at Rivers Casino & Resort and Park Manor Hotel, both 12.9km from the airport. The closest option is Pittsfield, MA (PSF-Pittsfield Municipal), only 4.8km away, with accommodations like The Central Downtown Inn & Suites, 3.2km from the airport, making it a convenient choice for your stay.

Frequently asked questions

What are the best hotels in Pittsfield that travellers recommend?
Hotel On North stands out as a premier choice in Pittsfield, boasting an exceptional score of 9.6. With its charming ambiance, guests are welcomed by cozy fireplaces and premium bedding, superb for couples seeking a romantic getaway or anyone wanting to unwind in style. The attentive room service adds a touch of luxury, ensuring an easy experience during your stay.

For families and groups, the Hilton Garden Inn Lenox Pittsfield, rated 9.2, is an excellent option. This hotel offers spacious suites with deep soaking bathtubs, ideal for relaxing after a day of exploring the nearby Berkshire attractions. Families will appreciate the indoor pool, providing a safe and fun environment for children to enjoy while parents relax nearby.

Another family-friendly choice is the Holiday Inn & Suites Pittsfield-Berkshires, which holds an 8.0 rating. This hotel features suites with mountain views and offers wedding services for those planning special events. The indoor pool is an inviting space for kids to play, while the hotel's convenient location makes it easy to explore local attractions together.

Lastly, the Berkshire Mountain Lodge, rated 8.8, provides a comfortable atmosphere with air-conditioned rooms and an indoor pool area with sun loungers, making it a great choice for travellers wanting a blend of relaxation and convenience. Whether you're traveling for business or leisure, Pittsfield's hotels offer attentive service and amenities designed for a stress-free stay.
What are the best family hotels in Pittsfield?
Hotel On North in Pittsfield is a charming family-friendly option, boasting an impressive traveller review score of 9.6. This hotel provides thoughtful amenities such as connecting rooms, free cribs, and a convenient sofa bed, making it easier for families to settle in comfortably. With room service and daily housekeeping, you can relax knowing that your needs will be attended to, allowing for a stress-free stay.

Another excellent choice is the Hilton Garden Inn Lenox Pittsfield, which enjoys a review score of 9.2. This hotel features a refreshing pool, superb for family fun, alongside connecting rooms and free cribs to accommodate your little ones. Families will appreciate the added convenience of a snack bar and microwave in the rooms, making late-night snacks and quick meals a breeze.

For those looking for even more amenities, the Holiday Inn & Suites Pittsfield-Berkshires, rated 8.0 by guests, offers unique features like child-friendly window designs and free rollaway beds. This property is particularly welcoming for families, with options for connecting rooms and complimentary breakfast for children, ensuring everyone starts their day off right. With a lovely garden for outdoor relaxation, it's an ideal retreat for families seeking both comfort and convenience in the Berkshires. Find more child-friendly accommodations in Pittsfield.
What are the top pet-friendly hotels in Pittsfield?
Hotel On North, which boasts an impressive traveller review rating of 9.6, offers a warm and friendly setting for both you and your furry companions. This charming hotel features a variety of amenities designed to enhance your stay, including air-conditioned rooms with premium bedding and free Wi-Fi. The inviting fireplace in the common area creates a cozy ambiance, great for relaxation after a day of exploring the picturesque Berkshires.

For families traveling with pets, the Hilton Garden Inn Lenox Pittsfield is another excellent choice, earning an excellent review score of 9.2. This hotel not only welcomes pets but also provides spacious suites that include kitchen facilities, making it convenient for families to prepare meals. Kids can enjoy splashing around in the indoor pool while parents unwind in the adjacent hot tub.

Whether you're planning a family getaway or a quick escape with your beloved pet, these hotels offer attentive service and the comforts of home, ensuring an easy experience. The Berkshire Mountain Lodge, rated 8.8, also features pet-friendly amenities and is ideal for those seeking outdoor adventures, including skiing and hiking, making it a great option for adventurous couples or families looking to create lasting memories.

With such a variety of choices, you can easily find a pet-friendly haven in Pittsfield that aligns with your travel style and preferences. See more pet-friendly hotels in Pittsfield.
What are the best budget hotels in Pittsfield?
Hotel On North is a standout option in Pittsfield, boasting an outstanding score of 9.6. This welcoming hotel provides a blend of modern amenities and a cozy atmosphere, making it a great choice for travellers. Guests appreciate the spacious rooms featuring premium bedding, a sofa bed for extra comfort, and a fireplace for a warm and inviting ambiance. Plus, with free self-parking and WiFi, convenience is at your fingertips.

For families, the Hilton Garden Inn Lenox Pittsfield is another excellent choice, rated 9.2 by guests. This property features spacious suites and an inviting indoor pool, great for children to splash around while parents relax. The availability of cribs for the little ones and free toiletries ensures a straightforward stay, allowing families to focus on making memories.

If you're considering a ski getaway, the Berkshire Mountain Lodge, rated 8.8, is an appealing option with its indoor pool and proximity to ski rentals nearby. It's ideal for families looking to enjoy winter sports together.

Each of these properties is designed to create an easy experience, allowing you to enjoy your trip while knowing that quality service and comfort are well taken care of. Whether you're planning a family adventure or a romantic escape, Pittsfield has something for everyone. View all budget hotels in Pittsfield.
When is the best time to go to Pittsfield?
The most popular time to visit Pittsfield is in July, when the region bursts into life with numerous outdoor events and activities. During this peak season, which runs from June to August, visitors can enjoy warm temperatures averaging around 25°C, superb for exploring the scenic beauty of the Berkshires.

As you wander through the lush surroundings, you'll find a wealth of options for outdoor adventures, from hiking the picturesque trails of the nearby mountains to enjoying a leisurely afternoon at one of the charming local lakes. The pleasant climate also makes it an ideal time for sightseeing, allowing you to immerse yourself in the rich cultural tapestry that Pittsfield has to offer, including art galleries, theatres, and historic sites.

For those seeking a bit more tranquillity, consider planning your visit in September. This month often features delightful weather with cooler temperatures averaging around 20°C, making it a fantastic time to enjoy the vibrant autumn foliage without the summer crowds. You'll still have access to many of the outdoor activities and cultural events, but with a more relaxed atmosphere that allows for a deeper connection with the destination.
Where can I find the best nightlife in Pittsfield?
Pittsfield, a charming city in the Berkshires, offers a laid-back atmosphere with a handful of nightlife options that cater to different tastes.

For those looking for a lively evening, the downtown area is where you'll find a selection of bars and pubs great for socialising. The Tap House, known for its extensive craft beer selection, is a popular spot among locals and visitors alike. It provides a relaxed environment to unwind after a day of exploring the scenic surroundings.

If you're interested in live music, the Colonial Theatre often hosts performances that can make for an entertaining night out. Check their schedule to see if there's a show that piques your interest during your visit.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Pittsfield.
How can I save on a Pittsfield hotel booking with Expedia?
Members always get our best prices. Find our best Pittsfield hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Pittsfield hotel?
Prices for hotels in Pittsfield often vary, but you can find a great deal from CA $97 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.