Pittsfield Packages (Flight + Hotel)

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    Save up to ฿4,531 when you book a flight and hotel together*
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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 ฿2,600 per night from 7 Sept to 8 Sept
฿2,600
฿2,821 total
7 Sept - 8 Sept
includes taxes & fees
6.6/10 (681 reviews)
"Bed extremely comfortable"

Reviewed on 7 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 ฿3,973 per night from 18 Aug to 19 Aug
฿3,973
฿4,310 total
18 Aug - 19 Aug
includes taxes & fees
7.6/10 Good! (1,011 reviews)
"Clean facility, friendly staff"

Reviewed on 11 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! (667 reviews)
"Bed was not comfortable small shower"

Reviewed on 10 Aug 2025

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Weirs Beach Motel and Cottages
See all 1,167 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 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.