Pittsfield hotels
Search and compare hundreds of travel sites at once for hotels in Pittsfield, Massachusetts. Bundle your hotel + flight and save!
Let KAYAK do the searching
Best Pittsfield hotels
Most recommended Pittsfield hotels
Top Pittsfield hotels with parking
How much is a Pittsfield hotel?
Here are our most popular & best value hotels3 stars
When to book a hotel in Pittsfield
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 Saturday. The opposite is true for, Wednesday, which is usually the most expensive day.
- Book at least 78 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 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 Yankee, Trademark Collection by Wyndham, Howard Johnson by Wyndham Lenox and Gateways Inn & Restaurant.