Pittsfield Holidays from £1,361

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Top Pittsfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was £1,907, price is now £1,361 per person
£1,361
per person
14 Sept - 19 Sept
found 8 hours ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on 23 May 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £3,687, price is now £2,406 per person
£2,406
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was £2,092, price is now £1,459 per person
£1,459
per person
16 Oct - 21 Oct
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (217 reviews)

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was £2,474, price is now £1,748 per person
£1,748
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (5,143 reviews)
Staff was amazing, super friendly and helpful. Room was perfect and blackout drapes appreciated.

Reviewed on 2 Aug 2026

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Save 100% on your flight
Price was £2,051, price is now £1,450 per person
£1,450
per person
23 Sept - 29 Sept
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (1,006 reviews)

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

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 £99 per night from 16 Aug to 17 Aug
£99
16 Aug - 17 Aug
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Check in was awful. Only one girl who didn't know what see was doing. Finally after six people were in line waiting to check in she finally called someone else to help. This person pretty much did all the check ins. Check in time is 3pm, if you go early they will charge you $30 for am early check ..."

Reviewed on 2 Aug 2026

Best Western Plus Landmark Inn
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 £72 per night from 31 Aug to 1 Sept
£72
31 Aug - 1 Sept
includes taxes & fees
6.8/10 (922 reviews)
"Friendly enough but offered little to no info about the amenities such as wifi password, beach access, etc. Room was no frills, but clean. Never could find the picturesque deck with the blue lounge chairs in the photos or only some rooms offered chairs to sit outside. TV remote didn't work. If you're ..."

Reviewed on 2 Aug 2026

Winnisquam Lake Inn
The Naswa Resort

The Naswa Resort

3 out of 5
1086 Weirs Blvd Laconia NH
The price is £169 per night from 19 Aug to 20 Aug
£169
19 Aug - 20 Aug
includes taxes & fees
8.6/10 Excellent! (804 reviews)
"Excellent dining options and a very beautiful on the water setting. Multiple options for activities. Rooms are not fancy but spacious with killer balconies. This resort hits just the right spot."

Reviewed on 1 Aug 2026

The Naswa Resort
See all 1,259 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
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Stay near popular Pittsfield attractions

Drake Field

Drake Field hosts the colourful annual Rotary Balloon Festival, a highlight of Pittsfield's summer. Stroll the riverside trail or relax in the gazebo while watching hot air balloons fill the August sky.
See properties

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.