Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa
Price was $353, price is now $257 per person
$257
per person
May 8 - May 10
found 3 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.
Boston Lodge and Suites
Save 100% on your flight
Price was $2,176, price is now $1,252 per person
$1,252
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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 Colonnade Hotel Back Bay
Price was $1,296, price is now $852 per person
$852
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
The Cove At Yarmouth
Save 100% on your flight
Price was $874, price is now $584 per person
$584
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Wild Animal Lagoon and Bay View Street Beach are located nearby.
Chatham Bars Inn
Save 100% on your flight
Price was $2,914, price is now $1,950 per person
$1,950
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Chatham Fish Pier are located nearby.
Boston Harbor Hotel
Save 100% on your flight
Price was $2,639, price is now $1,770 per person
$1,770
per person
Apr 2 - Apr 7
found 24 hours 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 Boston Common are located nearby.
The Langham, Boston
Save 100% on your flight
Price was $1,144, price is now $795 per person
$795
per person
Apr 9 - Apr 12
found 1 day 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 New England Aquarium and Boston Common are located nearby.
The Charles Hotel
Save 100% on your flight
Price was $1,625, price is now $1,162 per person
$1,162
per person
May 13 - May 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
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.
Sat, Jun 6 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Thu, Mar 5 - Thu, Mar 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$116 Roundtrip, found 5 days ago
$116
Roundtrip
found 5 days ago
Tue, Apr 7 - Sat, Apr 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$142 Roundtrip, found 19 hours ago
$142
Roundtrip
found 19 hours ago
Thu, Mar 19 - Sun, Mar 22
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$177 Roundtrip, found 22 hours ago
$177
Roundtrip
found 22 hours ago
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