Pittsfield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Pittsfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,286, price is now $899 per person
$899
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,459, price is now $937 per person
$937
per person
Mar 27 - Apr 1
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,658, price is now $1,783 per person
$1,783
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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 Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was $1,393, price is now $951 per person
$951
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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 Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was $1,696, price is now $1,185 per person
$1,185
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Stay at this 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 Boston Common and TD Garden are located nearby.
The Newbury Boston
Back Bay
Save 100% on your flight
Price was $1,872, price is now $1,328 per person
$1,328
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Top Hotel Deals
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
10.99 km from city center
Stay at this cabin in Epsom. Enjoy free parking, patios, and climate control. Popular attractions James Park and Epsom Public Library are located nearby.
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
22.7 km from city center
Book a stay at this business-friendly hotel in Bow. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Comfort Inn Concord South End
71 Hall St Concord NH
20.77 km from city center
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
34.01 km from city center
Book a stay at this spa hotel in Sanbornton. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff in our reviews. Popular attractions ...
Fireside Inn & Suites Gilford
17 Harris Shore Road Gilford NH
30.95 km from city center
Book a stay at this business-friendly hotel in Gilford. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
Winnisquam Lake Inn
788 Laconia Rd Tilton NH
26.32 km from city center
Stay at this hotel in Tilton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
DoubleTree by Hilton Downtown Concord
172 N Main St Concord NH
20.26 km from city center
Book a stay at this business-friendly hotel in Concord. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Best Western Plus Landmark Inn
480 Main Street Laconia NH
27.1 km from city center
Book a stay at this business-friendly hotel in Laconia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Homewood Suites by Hilton Dover
21 Members Way Dover NH
35.7 km from city center
Stay at this hotel in Dover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Dover ...
The Centennial
96 Pleasant St Concord NH
21.25 km from city center
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Tru by Hilton Concord
South Main Street, 406 Concord NH
21.99 km from city center
Stay at this hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Best Western Concord Inn & Suites
97 Hall St Concord NH
20.88 km from city center
Stay at this hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Holiday Inn Express Hotel & Suites Rochester by IHG
77 Farmington Rd Rochester NH
25.96 km from city center
Book a stay at this business-friendly hotel in Rochester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Feb 14 - Tue, Feb 24
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$115 Roundtrip, found 17 hours ago
$115
Roundtrip
found 17 hours ago
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$167 Roundtrip, found 22 hours ago
$167
Roundtrip
found 22 hours ago
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$187 Roundtrip, found 22 hours ago
$187
Roundtrip
found 22 hours ago
Tue, Mar 3 - Tue, Mar 10
CLT
Charlotte-Douglas Intl.
MHT
Manchester-Boston Regional
$201 Roundtrip, found 16 hours ago
$201
Roundtrip
found 16 hours ago
Thu, Mar 5 - Mon, Mar 9
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$207 Roundtrip, found 16 hours ago
$207
Roundtrip
found 16 hours ago