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Pittsfield hotels

Wed 26/6
Thu 27/6

Search hundreds of travel sites at once for hotels in Pittsfield, Massachusetts

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Best Pittsfield hotels

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Most recommended Pittsfield hotels

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The Dewey - Lenox - Dining room
The Dewey
R2 448+
R2 448+
Parking
Free Wi-Fi
Air conditioning
The Yankee, Trademark Collection by Wyndham - Lenox - Bedroom
R4 428+
Parking
Free Wi-Fi
Pool
Air conditioning
R2 890+
Parking
Free Wi-Fi
Pool
Air conditioning
R1 578+
Free Wi-Fi
Pool
Air conditioning
The Whitlock
R2 237+
R2 237+
Parking
Free Wi-Fi
Air conditioning
Hampton Terrace Inn
9.2 Wonderful
R7 782+
R7 782+
Parking
Free Wi-Fi
Pool
Air conditioning
R6 090+
Parking
Free Wi-Fi
Pool
Pet-friendly
The Lenox Collection
8.8 Very Good
R5 544+
R5 544+
Parking
Free Wi-Fi
Air conditioning
The Cornell Inn
9.4 Wonderful
R6 253+
R6 253+
Parking
Free Wi-Fi
Air conditioning
Wheatleigh
R16 539+
R16 539+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Hotel on North
9 Wonderful
R5 898+
R5 898+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Yankee Suites Extended Stay
9.1 Wonderful
R2 705+
R2 705+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R7 385+
Parking
Free Wi-Fi
Pool
Pet-friendly

Top Pittsfield hotels with parking

Show all
Best Western PLUS Berkshire Hills Inn & Suites - Pittsfield - Bedroom
Parking
Free Wi-Fi
Fairbridge Inn Express Pittsfield - Pittsfield - Bedroom
R1 719+
Parking
Free Wi-Fi
Life House Berkshires
8 Very Good
R5 669+
R5 669+
Parking
Free Wi-Fi
Eastgate Inn B&B
10 Wonderful
R6 239+
R6 239+
Parking
Free Wi-Fi

How much is a Pittsfield hotel?

Here are our most popular & best value hotels

3 stars

Good to know

Low season

March

High season

July

Average price (weeknight)

R2 752

Average price (weekend night)

R4 753
Cheapest month to stay with an average 44% drop in price.
Most expensive month to stay with an average 95% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a hotel in Pittsfield

Price per night / 3-star hotel. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Pittsfield hotel deals

  • If you’re looking for a cheap hotel in Pittsfield, you should consider visiting during the low season. You'll find cheaper accommodations in Pittsfield in March and April.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Pittsfield if you stay on a Monday. The opposite is true for, Thursday, which is usually the most expensive day.
  • Book at least 44 days before your stay begins to get the best price for your Pittsfield accommodation.
  • Avid historians who want to delve into the area’s heritage will be pleased to hear about staying at a hotel near Cheshire Road called Econo Lodge, only an 8-minute drive away from Berkshire Museum. This property has a business center, free high-speed Internet access, and an exercise room.
  • Theater enthusiasts who want to entertain themselves to a concert should plan and lodge at a hotel near South Street in Pittsfield. The thoughtfully designed Hotel On North is less than a 3-minute drive away from The Colonial Theater and has its own art gallery for guests to enjoy.
  • Want to hit the outdoors and do some skiing? Booking a room around Dan Fox Drive will provide easy access to skiing facilities, water slides, and snow sport equipment rentals. The Hilton Garden Inn Lenox Pittsfield is only a minute drive away and has well-equipped amenities, including an indoor heated pool and hot tub.
  • Fishing buffs who want to hit the lake and try their luck at catching a Largemouth Bass will be glad to hear about several hotels near Lake Onota, such as the Berkshire Inn. The hotel is about a 7-minute drive away and has spacious rooms with free Wi-Fi, and treats its guests to complimentary continental breakfast.
  • Those who want to enjoy a tennis tournament and having a good time should consider securing a room near Dan Fox Dr, like the Berkshire West Athletic Club that lies along the same route. Howard Johnson by Wyndham Lenox is a hotel that sits about a 4-minute drive away, and its outdoor pool, sauna, and mountain views make it unbeatable.

FAQs when booking a hotel in Pittsfield

  • Are there any hotels in a scenic part of the Pittsfield area?

    Some spots in Pittsfield provide views ideal for photography, particularly areas near Mount Greylock State Reservation. Vacation Village in the Berkshires is located a 20-minute drive away and commands a stunning view of the Jiminy Peak ski area from the well-furnished patios and balconies. We recommend booking in advance to secure a good rate.

  • Which hotels are within walking distance of dining options?

    Downtown Pittsfield is known for its diverse dining spots, offering both locally-inspired dishes and international flavors. If you wish to be only a few steps away from a selection of delicacies, consider booking a room along North St. The upscale Holiday Inn & Suites Pittsfield-Berkshires sits in the heart of this area.

  • Where is lodging near convenient public transport?

    If you want easy access to public transport during your stay in Pittsfield, consider staying along Columbus Ave, as this is where many of the local buses have their departure and arrival terminals, such as Greyhound. Best Western PLUS Berkshire Hills Inn & Suites also sits conveniently on this route.

  • Which are the best places to stay in Pittsfield with the kids?

    Those visiting Pittsfield with family may want to book their rooms near Pittsfield State Forest, as it has an extensive trail for outdoor activities such as biking, hiking, and horse riding. The family-friendly Lanesboro Country Inn is an 11-minute drive away.

  • How much does a hotel cost in Pittsfield?

    The average price of a double room in Pittsfield is R5 568 per night. In the last 3 days, KAYAK found great deals as cheap as R2 355 per night.

  • How do I find a hotel in central Pittsfield?

    After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Pittsfield districts. You can also do a search using the city map to choose a specific location, like Pittsfield city centre

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Pittsfield hotels with free parking?

    There are many hotels in Pittsfield that offer both parking and free parking. Popular choices among KAYAK users include The Dewey, The Yankee, Trademark Collection by Wyndham and Howard Johnson by Wyndham Lenox.

Where to stay in Pittsfield?

Our map will help you find the perfect place to stay in Pittsfield by showing you the exact location of each hotel.