Rockland Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Janine Edmondson
Rockland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Price was $853, price is now $671 per person
$671
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star 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.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,048, price is now $1,381 per person
$1,381
per person
Nov 23 - Nov 29
found 1 day 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 Faneuil Hall Marketplace are located nearby.
Porter Square Hotel
Porter Square
Price was $1,060, price is now $761 per person
$761
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star 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 Encore Boston Harbor are located nearby.
Revere Hotel Boston Common
Bay Village
Price was $1,037, price is now $787 per person
$787
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the bar in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Bostonian Boston
Government Center
Price was $933, price is now $723 per person
$723
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
Hotel Commonwealth
Fenway–Kenmore
Price was $1,051, price is now $821 per person
$821
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
Top Hotel Deals
Seaport Hotel Boston
1 Seaport Lane, Boston, MA
26.38 km from city center
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
The Revolution Hotel
40 Berkeley Street, Boston, MA
27.11 km from city center
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful ...
citizenM Boston North Station
70 Causeway Street, Boston, MA
28.75 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 ...
The Dagny Boston
89 Broad Street, Boston, MA
27.63 km from city center
Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
26.24 km from city center
Stay at this 5-star 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
27.55 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 ...
citizenM Boston Back Bay
408 Newbury street, Boston, MA
28.03 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 ...
Encore Boston Harbor
1 Broadway, Everett, MA
31.89 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 ...
Harborside Inn Of Boston
185 State St, Boston, MA
27.82 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 ...
Sheraton Boston, a Marriott Hotel
39 Dalton St, Boston, MA
27.67 km from city center
Book a stay at this eco-certified hotel in Boston. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
Hilton Boston Logan Airport
One Hotel Drive, Boston, MA
27.66 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 ...
Club Quarters Hotel Faneuil Hall, Boston
161 Devonshire St, Boston, MA
27.66 km from city center
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Wyndham Boston Beacon Hill
5 Blossom Street, Boston, MA
28.53 km from city center
Stay at this 3.5-star business-friendly hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
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.
Thu, Nov 13 - Sat, Nov 15
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$218 Roundtrip, found 3 hours ago
$218
Roundtrip
found 3 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$298 Roundtrip, found 3 hours ago
$298
Roundtrip
found 3 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$506 Roundtrip, found 3 hours ago
$506
Roundtrip
found 3 hours ago