Pittsfield hotels

Search hundreds of travel sites at once for hotels in Pittsfield, Massachusetts. Bundle your hotel + flight and save!

Pittsfield
Jun 29 — Jun 302
Pittsfield
Wed 6/29
Thu 6/30

Good to know

Low season

March

High season

August

Average price (weeknight)

$165

Average price (weekend night)

$268
Cheapest month to stay with an average 47% drop in price.
Most expensive month to stay with an average 57% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Best Pittsfield hotels

Top rated hotels in Pittsfield

Show all
The Cornell Inn - Lenox - Lounge
The Cornell Inn
9.3 Excellent
$307+
$307+
Parking
Free Wi-Fi
33 Main - Lenox - Restaurant
33 Main
9.5 Excellent
$562+
$562+
Parking
Free Wi-Fi
Hotel on North - Pittsfield - Lounge
Hotel on North - Pittsfield - Lounge
Hotel on North
8.9 Excellent
$312+
$312+
Parking
Free Wi-Fi
Pet friendly
The Whitlock - Lenox - Lounge
The Whitlock - Lenox - Lounge
The Whitlock
8.7 Excellent
$362+
$362+
Parking
Free Wi-Fi
Yankee Inn - Lenox - Bedroom
Yankee Inn - Lenox - Bedroom
Yankee Inn
8.4 Excellent
$211+
$211+
Parking
Free Wi-Fi
Pool
Whistler's Inn - Lenox - Building
Whistler's Inn - Lenox - Building
Whistler's Inn
8.5 Excellent
$249+
$249+
Parking
Free Wi-Fi
Pet friendly
Yankee Suites Extended Stay - Pittsfield - Balcony
Yankee Suites Extended Stay - Pittsfield - Balcony
Yankee Suites Extended Stay
8.6 Excellent
$255+
$255+
Parking
Free Wi-Fi
Pet friendly
The Dewey - Lenox - Dining room
The Dewey - Lenox - Dining room
The Dewey
8.3 Excellent
$354+
$354+
Free Wi-Fi
Pet friendly
Wheatleigh - Lenox - Bedroom
Wheatleigh - Lenox - Bedroom
Wheatleigh
9.7 Excellent
$2,012+
$2,012+
Parking
Free Wi-Fi
Pool
Pet friendly
Apple Tree Inn - Lenox - Lounge
Apple Tree Inn - Lenox - Lounge
Apple Tree Inn
7.8 Good
$324+
$324+
Parking
Free Wi-Fi
Pool
Seven Hills Inn - Lenox - Lounge
Seven Hills Inn - Lenox - Lounge
Seven Hills Inn
7.7 Good
$280+
$280+
Parking
Free Wi-Fi
Pet friendly
The Constance - Lenox - Bedroom
The Constance - Lenox - Bedroom
The Constance
7.6 Good
$348+
$348+
Parking
Free Wi-Fi

How much is a Pittsfield hotel?

Here are our most popular & best value hotels

3 stars

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 December.
  • 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, Friday, which is usually the most expensive day.
  • Book more than 90 days before your stay begins to get the best price for your Pittsfield accommodation.
  • The cheapest 3-star hotel room in Pittsfield found on KAYAK in the last 2 weeks was $135, while the most expensive was $588.
  • How long should you stay? KAYAK users usually book their accommodation in Pittsfield for 2 days.
  • 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

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.