Pittsfield Holidays

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Top Flight + Hotel Deals in Pittsfield

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
23 Mar - 27 Mar
found 19 hours ago
Return direct flight included
Cork (ORK) to Boston (BOS)
8.8/10 Excellent! (1,014 reviews)
A little outdated despite the gorgeous architecture. Also got placed in a king suite with a connecting door to another guest’s room and we could hear EVERYTHING. Some front desk staff were really nice and welcoming whereas others weren’t so kind.

Reviewed on 29 Jan 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
23 Mar - 27 Mar
found 19 hours ago
Return direct flight included
Cork (ORK) to Boston (BOS)
9.6/10 Exceptional! (1,006 reviews)
The views to the harbor were beautiful! The large windows are amazing to enjoy the view in the room. The service was excellent! Great attention to small details!! Just need to improve their menu for better food options for vegetarians/vegans. Other than that, I look forward to returning!

Reviewed on 28 Jan 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
23 Mar - 27 Mar
found 19 hours ago
Return direct flight included
Cork (ORK) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
Impeccable service.

Reviewed on 20 Jan 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
23 Mar - 27 Mar
found 19 hours ago
Return direct flight included
Cork (ORK) to Boston (BOS)
9.6/10 Exceptional! (93 reviews)
It’s my second time staying at a Raffles and it maintains the same level of hospitality and luxury comfort in Boston. Thank you.

Reviewed on 21 Jan 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
23 Mar - 27 Mar
found 19 hours ago
Return direct flight included
Cork (ORK) to Boston (BOS)
9.6/10 Exceptional! (2,675 reviews)
That was the second time I stay there

Reviewed on 29 Jan 2025

Top hotels in Pittsfield

Steele Hill Resorts
Steele Hill Resorts
3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is €193 per night from 3 Feb to 4 Feb
€193
includes taxes & fees
3 Feb - 4 Feb
8.2/10 Very Good! (600 reviews)
"The property was well maintained. Our toilet sidnt fluah correctly and with 1 call to the front desk they had someone there to replace thw toilet within minutes."

Reviewed on 27 Jan 2025

Steele Hill Resorts
Hampton Inn by Hilton Concord/Bow
Hampton Inn by Hilton Concord/Bow
2.5 out of 5
515 South St, Bow, NH
Fully refundableReserve now, pay when you stay
The price is €108 per night from 23 Feb to 24 Feb
€108
includes taxes & fees
23 Feb - 24 Feb
8.2/10 Very Good! (1,000 reviews)
"Great location, so convenient! Hotel is clean and comfortable. Highly recommend."

Reviewed on 26 Jan 2025

Hampton Inn by Hilton Concord/Bow
The Centennial
The Centennial
4 out of 5
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is €138 per night from 22 Feb to 23 Feb
€138
includes taxes & fees
22 Feb - 23 Feb
8.8/10 Excellent! (900 reviews)
"Poor signage. Doors just state “restaurant is closed”. No actual signage on the doors to indicate that you are entering the lobby of the hotel. Parking lot is icy and slippery. It last snowed 4 days prior. No care taken to ensure guest safety."

Reviewed on 26 Jan 2025

The Centennial
See all 1,082 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.

Frequently asked questions

How much does a Pittsfield holiday package cost?
You’ll find cheap prices from €2,039 on Expedia for your Pittsfield escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your holiday to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
The off-season is the best time to travel to Pittsfield if you’re trying to save. Another tip for scoring cheap Pittsfield holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Pittsfield?
The ideal length of your Pittsfield holiday depends on what you’d like to do. Typically, a handful of days to a week will give you enough time to check out all the major attractions and discover some hidden spots along the way.
How to find the best Pittsfield package deals?
Use Expedia’s filters to find some tempting Pittsfield package deals. When you begin your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Pittsfield package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s typically best to book your holiday package as soon as possible.
Is it cheaper to book a Pittsfield holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging accommodation and flights individually. Better still, you can customise your Pittsfield escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Pittsfield?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Pittsfield adventure.
How to plan a trip to Pittsfield?

  1. Choose when to go: Check your diary and pack your bags. Your favourite season and the type of activities available will also help you decide when to visit Pittsfield.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodation will likely be the biggest expense during your trip to Pittsfield.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you’d like to get to in Pittsfield. Then, estimate how long you’ll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Pittsfield holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.