Search Deals onSouth Boston Vacation Packages
South Boston Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Boston Hotel
Brighton
per person
Feb 13 - Feb 17
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
Boston Harbor Hotel
North End
per person
Feb 1 - Feb 8
found 14 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 Common are located nearby.
Pennyweight Hotel Boston, Curio Collection by Hilton
West End
Save 100% on your flight
per person
Feb 1 - Feb 8
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Hilton Boston Park Plaza
Bay Village
Save 100% on your flight
per person
Feb 1 - Feb 8
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this historic hotel in Boston. Enjoy 2 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
per person
Feb 17 - Feb 21
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Hotel Indigo Boston Garden, an IHG Hotel
West End
Save 100% on your flight
per person
Feb 1 - Feb 8
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
The Cove At Salem
Save 100% on your flight
per person
Feb 1 - Feb 8
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Common and Salem Witch Museum are located nearby.
The Westin Boston Seaport District
Seaport District
per person
Feb 17 - Feb 21
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
3-4 Night Vacations in South Boston
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in South Boston
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in South Boston
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
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. ...
Seaport Hotel Boston
1 Seaport Lane, Boston, MA
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 ...
Hampton Inn Boston Seaport District
670 Summer Street, Boston, MA
Stay at this 3-star business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Save an average of 15% on thousands of hotels when you're signed in
YOTEL Boston
65 Seaport Blvd, Boston, MA
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 ...
Aloft by Marriott, Boston Seaport District
401-403 D Street, Boston, MA
Stay at this 3-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
The Westin Boston Seaport District
425 Summer St, Boston, MA
Stay at this 4-star business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the ...
Homewood Suites by Hilton Boston Seaport District
670 Summer Street, Boston, MA
Stay at this 3-star business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Cambria Hotel Boston Downtown - Seaport
6 West Broadway, Boston, MA
Stay at this 3.5-star family-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Jan 18 - Sat, Jan 25
LAX
Los Angeles Intl.
BOS
Logan Intl.
$168 Roundtrip, found 4 hours ago
$168
Roundtrip
found 4 hours ago
Sat, Jan 11 - Wed, Jan 22
PDX
Portland Intl.
BOS
Logan Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Mon, May 5 - Tue, May 13
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,170 Roundtrip, found 2 days ago
$1,170
Roundtrip
found 2 days ago
Wed, May 14 - Wed, Oct 8
PEK
Capital Intl.
BOS
Logan Intl.
$1,381 Roundtrip, found 3 days ago
$1,381
Roundtrip
found 3 days ago
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