Vacation Packages to Massachusetts for 2025
Massachusetts Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Lakeside Inn
Save 100% on your flight
per person
Aug 18 - Aug 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
per person
Aug 18 - Aug 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star 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 Copley Square are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
per person
Aug 18 - Aug 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) 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 New England Aquarium and Boston Harbor are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
per person
Aug 18 - Aug 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
YOTEL Boston
Seaport District
Save 100% on your flight
per person
Aug 18 - Aug 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
The Verb Hotel
Fenway–Kenmore
Save 100% on your flight
per person
Aug 18 - Aug 25
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
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Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
28.7 km from city center
Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
citizenM Boston Back Bay
408 Newbury street, Boston, MA
25.01 km from city center
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...
Hyatt Regency Boston/Cambridge
575 Memorial Drive, Cambridge, MA
23.51 km from city center
Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the restaurant ...
citizenM Boston North Station
80-120 Causeway Street, Boston, MA
26.71 km from city center
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 ...
Copley Square Hotel, a FOUND Hotel
47 Huntington Ave, Boston, MA
25.8 km from city center
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the ...
The Godfrey Hotel Boston
505 Washington Street, Boston, MA
26.99 km from city center
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
Harborside Inn Of Boston
185 State St, Boston, MA
27.58 km from city center
Stay at this 4-star hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our ...
Encore Boston Harbor
1 Broadway, Everett, MA
25.96 km from city center
Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
The Arcadian Hotel
1200 Beacon St, Brookline, MA
22.99 km from city center
Stay at this 3.5-star hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff ...
Hilton Boston Logan Airport
One Hotel Drive, Boston, MA
29.87 km from city center
Stay at this 4-star business-friendly hotel in Boston. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the restaurant ...
The Westin Copley Place, Boston, a Marriott Hotel
10 Huntington Ave, Boston, MA
25.87 km from city center
Stay at this 4-star eco-certified hotel in Boston. Enjoy 4 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hyatt Regency Boston Harbor
101 Harborside Drive, Boston, MA
29.7 km from city center
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff ...
Hilton Boston Park Plaza
50 Park Plaza, Boston, MA
26.41 km from city center
Book a stay at this historic hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
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.
Fri, Sep 12 - Tue, Sep 16
PDX
Portland
BOS
Boston
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Wed, Oct 15 - Mon, Nov 3
LAX
Los Angeles
BOS
Boston
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Fri, Sep 12 - Tue, Sep 16
PDX
Portland
BOS
Boston
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Tue, Oct 14 - Fri, Oct 31
LAX
Los Angeles
BOS
Boston
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Fri, Sep 12 - Tue, Sep 16
PDX
Portland
BOS
Boston
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Popular vacation package destinations in Massachusetts
- Boston Vacations
- Nantucket Vacations
- Provincetown Vacations
- Hyannis Vacations
- Chatham Vacations
- Falmouth Vacations
- Gloucester Vacations
- South Yarmouth Vacations
- Edgartown Vacations
- Plymouth Vacations
- Oak Bluffs Vacations
- Sandwich Vacations
- Dennis Port Vacations
- West Yarmouth Vacations
- Springfield Vacations
- Worcester Vacations
- Brewster Vacations
- Rockport Vacations
- Dennis Vacations
- Wellfleet Vacations
- Eastham Vacations
- Lenox Vacations
- Foxboro Vacations
- North Truro Vacations
- Orleans Vacations
- Harwich Vacations
- Truro Vacations
- Newburyport Vacations
- Vineyard Haven Vacations
- Mashpee Vacations
- Amherst Vacations
- Sturbridge Vacations
- Marlborough Vacations
- Williamstown Vacations
- Winchendon Vacations
- Pittsfield Vacations
- Great Barrington Vacations
- Northampton Vacations
- East Falmouth Vacations
- Framingham Vacations
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