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.
Hotel Ivy Boston Common
Bay Village
Save 100% on your flight
Price was $1,861, price is now $1,069 per person
$1,069
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
Price was $5,814, price is now $3,823 per person
$3,823
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this beach guesthouse in East Wareham. Enjoy free WiFi, a private beach, and free bicycles on site. Popular attractions Onset Bay Center - Buzzards Bay Coalition and Onset Beach are located nearby.
The Atlas Hotel
Allston
Save 100% on your flight
Price was $1,788, price is now $1,184 per person
$1,184
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
South Bend (SBN) 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.
The Godfrey Hotel Boston
Downtown Boston
Save 100% on your flight
Price was $1,637, price is now $1,197 per person
$1,197
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
The Newbury Boston
Back Bay
Save 100% on your flight
Price was $3,669, price is now $2,697 per person
$2,697
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
South Bend (SBN) 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 Copley Square and Boston Common are located nearby.
The Mansion at Ocean Edge
Save 100% on your flight
Price was $2,367, price is now $1,762 per person
$1,762
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Ocean Edge Golf Club and Linnell Landing Beach are located nearby.
Top Hotel Deals
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 ...
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 ...
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 ...
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.
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 ...
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 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 ...
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 ...
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 ...
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 ...
Fairfield Inn & Suites by Marriott Hooksett
8 Bell Ave Hooksett NH
32.3 km from city center
Book a stay at this business-friendly hotel in Hooksett. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Loudon-Concord
2 Staniels Road Loudon NH
12.57 km from city center
Book a stay at this business-friendly hotel in Loudon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Lake Estate on Winnisquam
725 Laconia Road Tilton NH
25.99 km from city center
Book a stay at this luxury hotel in Tilton. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Lochmere Golf & Country Club and Tanger Outlets ...
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, Sep 5 - Sun, Sep 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$202 Roundtrip, found 9 hours ago
$202
Roundtrip
found 9 hours ago
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$237 Roundtrip, just found
$237
Roundtrip
just found
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$242 Roundtrip, just found
$242
Roundtrip
just found
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$272 Roundtrip, just found
$272
Roundtrip
just found
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$333 Roundtrip, just found
$333
Roundtrip
just found