Pittsfield Trip
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Top Pittsfield Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was ₹109,717, price is now ₹73,867 per person
₹73,867
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Great gym and staff. Kudos to Nicky at the front desk.
Reviewed on 22 Feb 2026
Boston Harbor Hotel
North End
Price was ₹238,390, price is now ₹125,647 per person
₹125,647
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) 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 25 Jan 2026
Eurostars The Boxer
West End
Save 100% on your flight
Price was ₹120,790, price is now ₹77,570 per person
₹77,570
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
I had a pleasant stay there. The receptionists are so nice and helpful. I came early before the checking time but they let me in. Extending reservation was also easy and they're helpful. They let me come back in after my buses were cancelled, and that's a very great service. They provided good amenities too. So far, it's been a comfortable stay in the hotel; and the location is quite near with the north station and stores if you need to buy meals just in case.
Reviewed on 24 Feb 2026
Raffles Boston
Back Bay
Save 100% on your flight
Price was ₹230,063, price is now ₹149,497 per person
₹149,497
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
The most perfect hotel and service I’ve ever experienced in my lifetime!
Reviewed on 24 Feb 2026
Top hotels in Pittsfield
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
Fully refundableReserve now, pay when you stay
The price is ₹8,875 per night from 29 Mar to 30 Mar
₹8,875
₹9,629 total
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
clean, staff and location
Reviewed on 24 Feb 2026
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
The price is ₹17,190 per night from 4 Mar to 5 Mar
₹17,190
₹18,651 total
4 Mar - 5 Mar
includes taxes & fees
8.4/10 Very Good! (769 reviews)
A lot of stuff missing in the kitchen. I ask for a cutting board which it never made it. Room was a bit dirty. Tv not working.
Reviewed on 20 Feb 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is ₹9,022 per night from 4 Mar to 5 Mar
₹9,022
₹9,789 total
4 Mar - 5 Mar
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Room was not cleaned well; shower had a lot of little black hairs in it +bad soap. Pool was broken, which was primary reason we booked here. Breakfast was good.
Reviewed on 22 Feb 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
