Pittsfield Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 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
Pittsfield Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Arbor Inn Motor Lodge
Price was S$3,910, price is now S$3,327 per person
S$3,327
per person
3 Jul - 8 Jul
found 1 day ago
Return flight included
Tokyo (TYO) to Boston (BOS)
6.4/10 (264 reviews)
The Owner was a very hospitable and i would come back breakfast was enough i enjoyed my stay vey clean room
Reviewed on 28 Sept, 2025
Josiah Keith House
Price was S$2,861, price is now S$2,610 per person
S$2,610
per person
3 Jul - 8 Jul
found 1 day ago
Return flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (34 reviews)
I was pleasantly surprised at the authenticity of the building and decor of the 18th century era. The owner puts great effort into making it an enjoyable experience. As a history fan this place surpassed my expectations. The breakfast was wonderful too!
Reviewed on 11 Apr, 2026
Hampton Inn Boston/Braintree
North Braintree
Price was S$3,009, price is now S$2,780 per person
S$2,780
per person
3 Jul - 8 Jul
found 1 day ago
Return flight included
Tokyo (TYO) to Boston (BOS)
8.2/10 Very Good! (1,001 reviews)
Decent continental breakfast. Pool was okay. Beds were not comfortable at all. I will say they were actually having professional carpet and upholstery cleaners come in during our stay. It is nice to know that hotels do this.
Reviewed on 14 Apr, 2026
Top hotels in Pittsfield
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
The price is S$260 per night from 30 Apr to 1 May
S$260
30 Apr - 1 May
includes taxes & fees
8.4/10 Very Good! (806 reviews)
Just had a nice lunch at Hilltop
Reviewed on 15 Apr, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 30 Apr to 1 May
S$145
30 Apr - 1 May
includes taxes & fees
7.8/10 Good! (1,000 reviews)
The breakfast had expired yogurt but other then that it was great stay
Reviewed on 13 Apr, 2026
Winnisquam Lake Inn
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
The price is S$109 per night from 7 May to 8 May
S$109
7 May - 8 May
includes taxes & fees
6.8/10 (837 reviews)
Great place great staff.
Reviewed on 17 Apr, 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
