Pittsfield Vacations from ￥345,496
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Pittsfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥811,240, price is now ￥547,834 per person
￥547,834
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 2026
Raffles Boston
Back Bay
Save 100% on your flight
Price was ￥928,686, price is now ￥657,442 per person
￥657,442
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
The most perfect hotel and service I’ve ever experienced in my lifetime!
Reviewed on Feb 24, 2026
Fairmont Copley Plaza, Boston
Back Bay
Price was ￥566,612, price is now ￥433,405 per person
￥433,405
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Great gym and staff. Kudos to Nicky at the front desk.
Reviewed on Feb 22, 2026
Find the Best Pittsfield Vacation Packages
Pittsfield Hotel Deals
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
Fully refundableReserve now, pay when you stay
The price is ￥15,227 per night from Mar 22 to Mar 23
￥15,227
￥16,521 total
Mar 22 - Mar 23
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
It was clean and comfortable and in a great central location. The breakfast had a lot of variety. We will definitely stay there again!
Reviewed on Mar 1, 2026
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
The price is ￥29,493 per night from Mar 2 to Mar 3
￥29,493
￥32,001 total
Mar 2 - Mar 3
includes taxes & fees
8.4/10 Very Good! (772 reviews)
Room was so old. There was constant banging above us very early in the am to very late at night. Sheets were terrible and scratchy. Dishes were all dirty. Pools and hot tub were clean though. Our room experience was not good
Reviewed on Feb 27, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is ￥15,480 per night from Mar 2 to Mar 3
￥15,480
￥16,795 total
Mar 2 - Mar 3
includes taxes & fees
7.8/10 Good! (1,002 reviews)
Great staff!
Reviewed on Feb 28, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
