
Pittsfield Vacations from $476
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The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.

DoubleTree by Hilton Manchester Downtown
Downtown Manchester
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,003 reviews)
The room was fine - nothing special. The hotel itself was nice. It was a good location for a day trip to Boston. We walked around some (to the nearby baseball stadium) and encountered several sketchy people which made my wife uncomfortable.
Reviewed on Aug 4, 2025


Raffles Boston
Back Bay
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.
Reviewed on Aug 5, 2025

Maverick Suites at 40 Temple St
Beacon Hill
Save 100% on your flight
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
7.4/10 Good! (89 reviews)
Had a 4 night stay at the Maverick Suites on Temple Street. I mainly booked this room to be close to my daughter, who lives a couple of doors down. The room is a bit tight for two people, but my friend & I made it work by sleeping 90 degrees on the double bed to turn it into more of a "short king". Room was very clean, however the one suggestion I would make is to use less of the strong-smelling cleaner (Fabioso?) or a more natural cleaner. Otherwise, the property felt safe and clean. Beautiful hardwood floors, nice bathroom & small kitchen area. Staff is very responsive via TEXT (not by phone). We requested clean towels etc, and they were very accommodating. Temple St. is walkable to many sites you'll want to check out in Boston via a walk or to the Park St T station. I would recommend staying at the Maverick Suites!
Reviewed on Jun 25, 2025

The Beverly
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Only complaint with 3 guests booked there was only one wash cloth provided one roll of toilet paper and one blanket for pull out bed no sheets other than that it was a good convenient place to stay
Reviewed on Aug 4, 2025
Pittsfield Hotel Deals

Winnisquam Lake Inn
788 Laconia Rd, Tilton, NH
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $107 total per night from Aug 10 to Aug 11
$107 total
Aug 10 - Aug 11
Total includes taxes and fees
6.8/10 (674 reviews)
"The beach area was a danger to get to. Had to cross a very busy highway and walk down a steep hill. Breakfast was skimpy and late."
Reviewed on Aug 5, 2025

Best Western Plus Landmark Inn
480 Main Street, Laconia, NH
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Aug 10 to Aug 11
$133 total
Aug 10 - Aug 11
Total includes taxes and fees
7.6/10 Good! (1,016 reviews)
Worth the trip
"Friendly , professional and worth the trip!"
Reviewed on Aug 4, 2025

Weirs Beach Motel and Cottages
396 Lakeside Ave, Laconia, NH
$157 nightly
The price is $170 total per night from Aug 7 to Aug 8
$170 total
Aug 7 - Aug 8
Total includes taxes and fees
8/10 Very Good! (658 reviews)
"Nice an cozy ..walk distance to board walk"
Reviewed on Aug 3, 2025
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.