Pittsfield Trips (flight + hotel)

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Top hotels in Pittsfield

The Centennial
The Centennial
4 out of 5
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is P6,817 per night from 14 Mar to 15 Mar
P6,817
P8,338 total
includes taxes & fees
Mar 14 - Mar 15
8.8/10 Excellent! (912 reviews)
"Beautiful place to stay clean Hugh ceilings just girgeous"

Reviewed on Feb 15, 2025

The Centennial
Fireside Inn & Suites Gilford
Fireside Inn & Suites Gilford
2.5 out of 5
17 Harris Shore Road, Gilford, NH
Fully refundableReserve now, pay when you stay
The price is P8,271 per night from 23 Feb to 24 Feb
P8,271
P8,974 total
includes taxes & fees
Feb 23 - Feb 24
8.6/10 Excellent! (732 reviews)
"Everyone was very polite. Easy checkin and checkout"

Reviewed on Feb 9, 2025

Fireside Inn & Suites Gilford
Steele Hill Resorts
Steele Hill Resorts
3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is P10,701 per night from 4 Mar to 5 Mar
P10,701
P11,611 total
includes taxes & fees
Mar 4 - Mar 5
8.2/10 Very Good! (604 reviews)
"Had fu pools awesome"

Reviewed on Feb 14, 2025

Steele Hill Resorts
See all 1,084 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 vacation 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 vacation 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 vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Pittsfield?
The ideal length of your Pittsfield vacation 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 vacation package as soon as possible.
Is it cheaper to book a Pittsfield vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can customize 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 vacation 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 favorite 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 accommodations 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 vacation package.

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