Pittsfield Holidays from £838

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Your Pittsfield Holiday

When you book a Pittsfield holiday package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theatre and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your holiday to Pittsfield to suit your style of travel, whatever that may look like.

Top Pittsfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Weathervane Motel

Weathervane Motel

2 out of 5
per person
1 Oct - 4 Oct
found 8 hours ago
Return flight included
Manchester (MAN) to Albany (ALB)
6.8/10 (666 reviews)
they are undergoing upgrading the facility. the owner/manager went out of his way to make my stay a good one.

Reviewed on 29 Jun 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
1 Oct - 4 Oct
found 8 hours ago
Return flight included
Manchester (MAN) to Albany (ALB)
7.4/10 Good! (491 reviews)
The property was historic and very quaint and the common areas were nice. Coffee was good. For the price paid -carpet in halls & elevator needed replaced/woodwork repainted. Air conditioner was a window unit/room outdated.

Reviewed on 14 Jul 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
per person
1 Oct - 4 Oct
found 8 hours ago
Return flight included
Manchester (MAN) to Albany (ALB)
9.4/10 Exceptional! (10 reviews)
The White House Inn

The White House Inn

3.5 out of 5
per person
1 Oct - 4 Oct
found 8 hours ago
Return flight included
Manchester (MAN) to Albany (ALB)
9.2/10 Wonderful! (206 reviews)
Beautiful location and gorgeous property.

Reviewed on 9 Jul 2025

Valley Craft Ales

Valley Craft Ales

2 out of 5
per person
1 Oct - 4 Oct
found 8 hours ago
Return flight included
Manchester (MAN) to Albany (ALB)
8.8/10 Excellent! (126 reviews)
To warm in hot weather, very small room and shower, floor tilted

Reviewed on 14 Jul 2025

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Population
43,300
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Jiminy Peak Mountain Resort, Norman Rockwell Museum and Bousquet Ski Area

Top hotels in Pittsfield

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is £105 per night from 27 Jul to 28 Jul
£105
27 Jul - 28 Jul
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
"Great"

Reviewed on 13 Jul 2025

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is £107 per night from 27 Jul to 28 Jul
£107
27 Jul - 28 Jul
includes taxes & fees
7.8/10 Good! (822 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on 16 Jul 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is £59 per night from 31 Jul to 1 Aug
£59
31 Jul - 1 Aug
includes taxes & fees
5.2/10 (741 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on 1 Jul 2025

FairBridge Inn Express
See all 1,357 properties in Pittsfield
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Pittsfield travel package cost?
Get your credit card ready, because a trip to Pittsfield starts from only £838. When you combine your hotels, flights and car rentals into a travel package, you'll pick up the biggest deals.
If I'm not able to travel, can I cancel my Pittsfield travel package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Pittsfield travel package in the last 24 hours? You may be able to make changes for free. If it's been longer than that, you may be charged a fee by your hotel, airline or car rental company. For further information, visit our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Pittsfield?
Combine your flights and hotels, throw in extras such as activities, and save with a Pittsfield travel package. You won't just score big discounts on your trip --- you'll have plenty of choice at your fingertips too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 properties throughout the world. Your next epic adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later Pittsfield holidays?
Expedia has joined forces with online lender Klarna to make booking your next trip easier on your budget. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in Pittsfield?
With loads to discover in Pittsfield, it'd be handy for you to lock in a hotel near its attractions. Bousquet Ski Area, Hancock Shaker Village and Pittsfield State Forest are some good ones to put on your to-do list.
What are the top hotels in Pittsfield?
Make a reservation at Holiday Village In The Berkshires. It's one of this neighbourhood's most popular properties. Another top-rated option in Pittsfield is The Black Swan Lee - Lenox, Ascend Hotel Collection.
How far in advance should I book my Pittsfield holiday?
Travellers are normally able to browse international flights on Expedia within 12 months of the departure date. Booking at the last minute? With a little bit of luck, it's still possible to score an affordable ticket only weeks before your flight.
What does an Expedia Pittsfield travel package include?
With Expedia, you can choose any combination of car rentals, flights and hotels to create your perfect Pittsfield travel package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Don't forget, the more you bundle, the more dollars you'll save!
What should I know before booking a Pittsfield travel package?
You'll score amazing savings when you bundle your hotels, flights and rental cars into a travel package. Not only that, booking everything in one spot just makes things easier. So why waste your money or time? Whether you're putting together a luxury city stay with your love or an affordable family break, take a look at our package deals today.
Can I choose my airline with a Pittsfield Expedia travel package?
Yes, of course. We have more than 550 airline partners around the world, so select the carrier that best suits your budget and travelling style.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.