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.
The Revolution Hotel
South End
$827
per person
Nov 20 - Nov 27
found 1 hour ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel
North End
$1,808
per person
Nov 20 - Nov 27
found 1 hour ago
Roundtrip flight included
Houston (IAH) 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 Faneuil Hall Marketplace and Boston Harbor are located nearby.
Great location. A bit pricey for the size room. Easy to get most places by walking .
Reviewed on Oct 4, 2026
Battery Wharf Hotel, Boston Waterfront
North End
$995
per person
Nov 20 - Nov 27
found 1 hour ago
Roundtrip flight included
Houston (IAH) 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.
The Godfrey Hotel Boston
Downtown Boston
$917
per person
Nov 20 - Nov 27
found 1 hour ago
Roundtrip flight included
Houston (IAH) 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.
Well located, clean, lovely staff, great café, nice bar, and very comfortable rooms… Even the “cozy” rooms are very comfortable! Everyone… valets who greet you upon arrival, Front Desk staff, housekeeping, etc., were all wonderfully friendly, helpful, kind, professional, and informative! Great stay!
Reviewed on Oct 6, 2026
The Ritz-Carlton, Boston
Downtown Boston
$1,220
per person
Nov 26 - Nov 30
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
A well run, beautiful classic hotel that never gets old. Loved our stay. Staff was exceptional, superb quality, and excellent location. But it is the people who truly make this Ritz Carlton special! They made our stay that much more enjoyable!
Reviewed on Oct 4, 2026
Top Hotel Deals
The Centennial
96 Pleasant St Concord NH
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. ...
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
Stay at this cabin in Epsom. Enjoy free parking, patios, and climate control. Popular attractions James Park and Epsom Public Library are located nearby.
Best Western Plus Landmark Inn
480 Main Street Laconia NH
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 ...
The Naswa Resort
1086 Weirs Blvd Laconia NH
Book a stay at this beach resort in Laconia. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
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 ...
Fireside Inn & Suites Gilford
17 Harris Shore Road Gilford NH
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
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
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 ...
The Lake Estate on Winnisquam
725 Laconia Road Tilton NH
Book a stay at this luxury hotel in Tilton. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Silver Lake and Lochmere Golf & Country Club ...
Comfort Inn Concord South End
71 Hall St Concord NH
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 ...
Super 8 by Wyndham Tilton/Lake Winnipesaukee
7 Tilton Rd Tilton NH
Book a stay at this business-friendly motel in Tilton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Best Western Concord Inn & Suites
97 Hall St Concord NH
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 ...
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
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 ...
Homewood Suites by Hilton Dover
21 Members Way Dover NH
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 The Children's ...
Weirs Beach Motel and Cottages
396 Lakeside Ave Laconia NH
Stay at this motel in Laconia. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Winnipesaukee ...
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, Oct 24 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$157
Roundtrip
found 5 hours ago
Thu, Nov 5 - Tue, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$329
Roundtrip
found 19 hours ago
Thu, Nov 5 - Tue, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$339
Roundtrip
found 19 hours ago
Thu, Nov 5 - Tue, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$369
Roundtrip
found 19 hours ago
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