Pittsfield Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 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
Top Flight + Hotel Deals in Pittsfield
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Price was €945, price is now €814 per person
€814
per person
19 Feb - 23 Feb
found 9 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
Everything was wonderful. The restaurant that is attached was great as well!!
Reviewed on 16 Jan 2026
DoubleTree Suites by Hilton Hotel Boston - Cambridge
Allston
Price was €1,065, price is now €908 per person
€908
per person
19 Feb - 23 Feb
found 9 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
8.8/10 Excellent! (1,000 reviews)
Bravo, the property close to everything we need
Reviewed on 14 Jan 2026
Top hotels in Pittsfield
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
Pittsfield NH
10/10 Exceptional! (33 reviews)
Place is beautiful and best to relax. The cabin was clean and perfect for me and my wife
Reviewed on 5 Oct 2025
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
Fully refundableReserve now, pay when you stay
The price is €95 per night from 25 Jan to 26 Jan
€95
25 Jan - 26 Jan
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Room was clean, pillows were soft, fridge, microwave. Staff were friendly and helpful. Breakfast was plentiful and fresh. Would def stay here again
Reviewed on 9 Jan 2026
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
The price is €124 per night from 21 Jan to 22 Jan
€124
21 Jan - 22 Jan
includes taxes & fees
9.6/10 Exceptional! (102 reviews)
It was nice and clean. The ambiance was extremely cozy. The staff were very nice and super attentive. This is perfect for those of us that needed to get out of the city and into a quiet, peaceful escape. Truly reccomend it!
Reviewed on 7 Jan 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.
