Vacation Packages to Massachusetts for 2026
Massachusetts Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Arcadian Hotel
Save 100% on your flight
Price was $644, price is now $453 per person
$453
per person
Feb 11 - Feb 17
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $1,455, price is now $781 per person
$781
per person
Feb 11 - Feb 17
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Porter Square Hotel
North Cambridge
Save 100% on your flight
Price was $866, price is now $542 per person
$542
per person
Feb 11 - Feb 17
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Studio Allston Hotel
Brighton
Save 100% on your flight
Price was $743, price is now $491 per person
$491
per person
Feb 11 - Feb 17
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Hotel 1868
Agassiz
Save 100% on your flight
Price was $790, price is now $551 per person
$551
per person
Feb 11 - Feb 17
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
The Bostonian Boston
Government Center
Save 100% on your flight
Price was $941, price is now $658 per person
$658
per person
Feb 11 - Feb 17
found 19 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
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Harborside Inn Of Boston
185 State St Boston MA
27.58 km from city center
Stay at this 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 reviews. ...
Hilton Boston Back Bay
40 Dalton St Boston MA
25.34 km from city center
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
28.7 km from city center
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
The Langham, Boston
250 Franklin St Boston MA
27.53 km from city center
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Dagny Boston
89 Broad Street Boston MA
27.61 km from city center
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...
Seaport Hotel Boston
1 Seaport Lane Boston MA
28.77 km from city center
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
The Westin Copley Place, Boston, a Marriott Hotel
10 Huntington Ave Boston MA
25.87 km from city center
Book a stay at this business-friendly hotel in Boston. Enjoy 4 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
The Godfrey Hotel Boston
505 Washington Street Boston MA
26.99 km from city center
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 ...
Encore Boston Harbor
1 Broadway Everett MA
25.96 km from city center
Book a stay at this 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 ...
Omni Parker House
60 School St Boston MA
27.04 km from city center
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
Hilton Boston Logan Airport
One Hotel Drive Boston MA
29.87 km from city center
Book a stay at this business-friendly hotel in Boston. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the restaurant ...
The Revolution Hotel
40 Berkeley Street Boston MA
26.48 km from city center
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 ...
The Newbury Boston
15 Arlington St Boston MA
26.27 km from city center
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 ...
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.
Tue, Apr 28 - Sat, May 2
PDX
Portland
BOS
Boston
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Fri, May 1 - Tue, May 5
PDX
Portland
BOS
Boston
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Fri, May 1 - Tue, May 5
PDX
Portland
BOS
Boston
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Wed, Sep 2 - Tue, Sep 8
PDX
Portland
BOS
Boston
$252 Roundtrip, found 4 days ago
$252
Roundtrip
found 4 days ago
Wed, Mar 25 - Tue, Mar 31
PDX
Portland
BOS
Boston
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago