Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Monticello Inn Framingham
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this motel in Framingham. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Fun and Games Family Entertainment Center and Jordan's Furniture are located nearby.
Lighthouse Inn
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star beach hotel in West Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Bass River Lighthouse are located nearby.
Sonesta Simply Suites Boston Braintree
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Braintree. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions F1 Boston and South Shore Plaza are located nearby.
The Walpole Motel
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this motel in Walpole. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Gillette Stadium and Family Funway Foxboro are located nearby.
Framingham Inn
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Framingham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Framingham Town Common and Old Village Hall are located nearby.
The Beverly
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Beverly. Enjoy free WiFi, free parking, and an in-room coffeemaker. Our guests praise the clean rooms in our reviews. Popular attractions Salem Witch Museum and Dogs by Design & Cats Too are located nearby.
The Cove At Salem
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Salem Common 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.
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 17 hours ago
$102
Roundtrip
found 17 hours ago
Sat, Aug 9 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Fri, Jun 13 - Sun, Jun 15
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Fri, Jul 11 - Sun, Jul 13
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
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