Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
Price was $622, price is now $458 per person
$458
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.
Great stay
Reviewed on Oct 29, 2026
Boston Lodge and Suites
Save 100% on your flight
Price was $1,030, price is now $597 per person
$597
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
Boston Harbor Hotel
Save 100% on your flight
Price was $1,542, price is now $912 per person
$912
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Four Seasons Hotel Boston
Save 100% on your flight
Price was $1,646, price is now $1,128 per person
$1,128
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Raffles Boston
Price was $1,562, price is now $1,102 per person
$1,102
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Langham, Boston
Price was $1,054, price is now $759 per person
$759
per person
Dec 19 - Dec 22
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
XStay Suites Mansfield
Price was $644, price is now $494 per person
$494
per person
Dec 4 - Dec 7
found 21 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Stay at this hotel in Mansfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Xfinity Center and National Black Doll Museum are located nearby.
The Atlas Hotel Boston Cambridge
Price was $770, price is now $599 per person
$599
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
Very clean and I love the modern, artsy decor. Excellent gym equipment too.
Reviewed on Oct 29, 2026
Pittsfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Pittsfield Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Dec 24 - Thu, Jan 7
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 1 hour ago
$122
Roundtrip
found 1 hour ago
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$148 Roundtrip, found 4 days ago
$148
Roundtrip
found 4 days ago
Thu, Nov 26 - Tue, Dec 8
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$174 Roundtrip, just found
$174
Roundtrip
just found
Fri, Jan 8 - Fri, Jan 22
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$206 Roundtrip, just found
$206
Roundtrip
just found
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