Pittsfield Vacations from NT$11,701

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The Latest Pittsfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts Surfside

InnSeason Resorts Surfside

3 out of 5
Price was NT$14,737, price is now NT$11,701 per person
NT$11,701
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
9.4/10 Exceptional! (348 reviews)
I loved being surrounded by water. This was a great location.

Reviewed on 2025/8/20

AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
Price was NT$19,374, price is now NT$14,976 per person
NT$14,976
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
9.4/10 Exceptional! (279 reviews)
Beautiful location and great amenities! Clean and comfortable rooms. Great, unique experience!

Reviewed on 2025/8/11

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was NT$21,283, price is now NT$16,790 per person
NT$16,790
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on 2025/8/25

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was NT$15,787, price is now NT$12,600 per person
NT$12,600
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
A simple but lovely place to stay!

Reviewed on 2025/8/25

Lighthouse Inn

Lighthouse Inn

3 out of 5
Price was NT$22,470, price is now NT$18,262 per person
NT$18,262
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
8.8/10 Excellent! (160 reviews)
Ended up in a room at the back of the property, which was inconvenient and not in great condition. The room and bedding were very low quality. Basic accommodations although nice location.

Reviewed on 2025/8/1

Find the Best Pittsfield Vacation Packages

Pittsfield Hotel Deals

The Centennial

The Centennial

4 out of 5
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (997 reviews)
Elegantly Unique
"Wonderful room. Friendly staff. We enjoyed the complimentary robes in the room. It was chilly in our room due to the drop in temperature outside in the midst of summer. The third floor could not compensate for that change. We also understand it is an old building so the heating is an old system. ..."

Reviewed on 2025/8/22

Get rates
The Centennial
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 NT$2,165 per night from Aug 28 to Aug 29
NT$2,165
NT$2,349 total
Aug 28 - Aug 29
includes taxes & fees
6.6/10 (703 reviews)
"The rooms are very nice clean and updated. Outdoor seating. Lots of traffic."

Reviewed on 2025/8/23

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 NT$3,468 per night from Sep 7 to Sep 8
NT$3,468
NT$3,763 total
Sep 7 - Sep 8
includes taxes & fees
7.6/10 Good! (1,016 reviews)
"Very clean, nice staff. Well maintained."

Reviewed on 2025/8/23

Best Western Plus Landmark Inn
See all 1,146 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 from NT$11,701 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.