Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Freepoint Hotel Cambridge, Tapestry Collection by Hilton

Save 100% on your flight

per person

Mar 6 - Mar 10

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Fenway Park and TD Garden are located nearby.

Fairmont Copley Plaza, Boston

Save 100% on your flight

per person

Mar 12 - Mar 16

found 23 hours ago

Roundtrip flight included

Washington (DCA) to Boston (BOS)

Stay at this 4.5-star luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Holly Tree Resort by VRI Americas

per person

Mar 22 - Mar 30

found 8 hours ago

Roundtrip flight included

New York (JFK) to Boston (BOS)

Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Cape Cod Inflatable Park and Englewood Beach are located nearby.

Boston Lodge and Suites

per person

Mar 4 - Mar 6

found 11 hours ago

Roundtrip flight included

Washington (DCA) to Boston (BOS)

Stay at this 4-star 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 Boston Common and Fenway Park are located nearby.

935 Ocean A Beachside Inn

Save 100% on your flight

per person

Feb 26 - Mar 5

found 1 hour ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Boston (BOS)

Stay at this 4-star beach inn in Hampton. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hampton Beach and North Beach are located nearby.

Boston Harbor Hotel

Save 100% on your flight

per person

Mar 12 - Mar 16

found 23 hours ago

Roundtrip flight included

Washington (DCA) to Boston (BOS)

Stay at this 5-star 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 Boston Common and TD Garden are located nearby.

citizenM Boston North Station

Save 100% on your flight

per person

Mar 12 - Mar 16

found 23 hours ago

Roundtrip flight included

Washington (DCA) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the bar 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

per person

Feb 7 - Feb 9

found 17 hours ago

Roundtrip flight included

Washington (DCA) to Boston (BOS)

Stay at this 4-star boutique 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.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.