Pittsfield Holidays from £848

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Top Pittsfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on 3 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
27 Oct - 3 Nov
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
Raffles is the most service oriented hotel we have ever stayed at. This place is amazing!!

Reviewed on 2 Aug 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
8 Sept - 14 Sept
found 13 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (358 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on 4 Aug 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
27 Oct - 3 Nov
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (2,696 reviews)
The staff really go above and beyond in customer service no questions were left unanswered, and assistance with finding our way around Boston. Special shout out to Maya, she really was helpful and considerate of our needs. Loved the property location which made our first time in Boston so much more special. If we are ever back in the area we would not hesitate to stay here again. Thanks again

Reviewed on 4 Aug 2025

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
1,600
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Alton Town Beach, New Hampshire International Speedway and Bow Lake

Top hotels in Pittsfield

Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd, Tilton, NH
Fully refundableReserve now, pay when you stay
The price is £73 per night from 6 Aug to 7 Aug
£73
6 Aug - 7 Aug
includes taxes & fees
6.8/10 (666 reviews)
"Our king size room view of the lake was spacoius and very comfortable bed. Bathroom was clean. After we checked on we made ourselves coffee downstairs amd sat on the front deck with patio tables and chairs. Only stayed one night like alot of people. Very close to Bank of Pavillion."

Reviewed on 2 Aug 2025

Winnisquam Lake Inn
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street, Laconia, NH
Fully refundableReserve now, pay when you stay
The price is £100 per night from 10 Aug to 11 Aug
£100
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,008 reviews)
Nice place
"Very nice place with great employees, great breakfast, and great water view of canal!"

Reviewed on 3 Aug 2025

Best Western Plus Landmark Inn
Weirs Beach Motel and Cottages

Weirs Beach Motel and Cottages

2 out of 5
396 Lakeside Ave, Laconia, NH
8/10 Very Good! (657 reviews)
Great Location, ok room
"No food on site. Bed is definitely not the worst I’ve slept in. Loved the remote check in process. So easy! Also extremely close to all of the Weird Beach happenings…such a short walk. Room could definitely benefit rom an upgrade. Had a strange smell…almost like someone had smoked in there or really ..."

Reviewed on 2 Aug 2025

Get rates
Weirs Beach Motel and Cottages
See all 1,162 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
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Frequently asked questions

Why should I book my Pittsfield holiday with Expedia?
With top-value flights, car hire and hotel options all in one convenient place, Expedia makes booking your Pittsfield adventure a piece of cake. What's more, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Pick from fabulous retreats, add your flights and/or a car hire (and maybe even some fun tours and activities!) and land incredible prices. Want to change your plans? Expedia offers a flexible cancellation policy for many bookings. To discover more, check out our Customer Service Portal link.
When is the best time of year to holiday in Pittsfield?
If you'd like to experience the excitement of Pittsfield in the peak season, plan your getaway for April, July and August. November, December and January are usually the quietest months of the year. With average daytime temperatures of -5ºC, January is the coolest period in Pittsfield. The warmest time of year is July, when you can expect averages of 21ºC during the day. Whatever the weather, you'll find plenty to keep you occupied here.
What is the top hotel for my holiday in Pittsfield?
Offering plenty of amenities and a cosy place to relax between adventures, The Centennial will make an ideal base for your Pittsfield holiday.
How do I get a cheap holiday to Pittsfield?
Our Pittsfield holidays promise plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities). But great bargains are just the beginning of your next amazing adventure. Book with Expedia and and you'll have over 400 air carriers and 321,000 hotel options worldwide to choose from. Whatever your style, there's a holiday here with your name on it. Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Pittsfield holiday?
There are plenty of things to explore while having a holiday in Pittsfield. New Hampshire International Speedway, Bow Lake, Canterbury Shaker Village and Upper Suncook Lake are among this destination's leading attractions.
Do I need a visa for my Pittsfield holiday?
Research the latest information on official government websites. Your nationality and whether you're visiting for work or pleasure will determine if you need a visa for Pittsfield. Find out about the application process, including any required documentation, turnaround times and fees. Start your application well in advance to allow plenty of time for processing. Some visas can take several weeks or even months to obtain, depending on the country.
What should I wear on my Pittsfield holiday?
Although everyone's fashion style differs, it can be helpful to have some guidelines for what type of clothes to bring during your holiday in Pittsfield. We recommend looking up style blogs before you head off for inspiration on fashion trends or dress codes. Pack your bags with confidence by checking the weather conditions in Pittsfield. July brings the warmest temperatures, with daily averages of 21ºC, while January days average -5ºC, making it the coolest time of the year.
What does an Expedia Pittsfield holiday include?
It all depends on what sort of trip you're contemplating. Pittsfield travel deals can include hotels, flights and car hires. You can mix and match to create the travel package that suits your style and budget. You can also add on experiences and activities after you've booked to pick up even bigger discounts. Discover a large selection of property types and choose one that suits your travel needs. The most in-demand rentals here are cabins and private holiday homes. With Expedia, you can easily design your Pittsfield retreat any way you want.
Does Expedia offer Book Now, Pay Later Pittsfield holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without using up all your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that fit all budgets, so you can lock in that well-deserved holiday sooner.
  • No-deposit holidays: Clicking the "book now" button is much easier with this payment plan. With no upfront fee for your escape, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Pittsfield Expedia holiday?
Yes, and with more than 400 airlines to pick from globally, it's all about choice. Look through the available options and see which airline fits your budget and needs.

* 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.