South Brookline Vacations from $430
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Your South Brookline Vacation
Your next great adventure is calling your name with a vacation package to South Brookline. Excitement, fun and good times — you're bound to find it in this neighborhood. When the time comes to sightsee, your trip to South Brookline should include a visit to Boston College and McMullen Museum. Expedia will help put your plans into action. Book your perfect South Brookline vacation today.
The Latest South Brookline Vacation Packages
Price found within the past 48 hours. Click for updated prices.
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Jan 28 - Feb 1
The Coonamessett + Flight
Falmouth
4 nights
8.8/10 - Excellent (724 reviews)
"The Coonamessett is a beautiful inn overlooking the water. The suite I stayed in was absolutely stunning. Breakfast is excellent with some vegan options such as mixed fruit and oat milk. The inn is extremely comfortable, clean, and well-maintained. My suite even had two walk-in closets."
Reviewed November 11, 2026
Roundtrip • Miami (MIA) - Boston (BOS)
FLL - BOS • Nonstop BOS - MIA • Nonstop
$430
per traveler
found 5 hours ago




Dec 17 - Dec 21
Boston Lodge and Suites + Flight
Dorchester
4 nights
8.4/10 - Very good (194 reviews)
"The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
Reviewed October 17, 2026
Roundtrip • Atlanta (ATL) - Boston (BOS)
ATL - BOS • Nonstop BOS - ATL • Nonstop
$452
per traveler
found 17 hours ago




Dec 19 - Dec 23
Boston Harbor Hotel + Flight
North End
4 nights
9.8/10 - Exceptional (1,000 reviews)
"!"
Reviewed November 10, 2026
Roundtrip • Atlanta (ATL) - Boston (BOS)
ATL - BOS • Nonstop BOS - ATL • Nonstop
Save 100% on your flight
$1,225
per traveler
found 1 day ago




Jan 28 - Feb 1
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight
East Wareham
4 nights
10/10 - Exceptional (11 reviews)
"We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape."
Reviewed July 27, 2026
Roundtrip • Miami (MIA) - Boston (BOS)
FLL - BOS • Nonstop BOS - MIA • Nonstop
$1,055
per traveler
found 3 hours ago




Jan 31 - Feb 3
Raffles Boston + Flight
Back Bay
3 nights
9.6/10 - Exceptional (357 reviews)
Roundtrip • Fort Lauderdale (FLL) - Boston (BOS)
FLL - BOS • Nonstop BOS - FLL • 1 stop
$1,024
per traveler
found 22 hours ago
Where to stay in South Brookline
Find the best South Brookline areas and neighborhoods for the activities you enjoy most.





View properties in map for Downtown Boston
Downtown Boston
Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.





View properties in map for Back Bay
Back Bay
Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.





View properties in map for Seaport District
Seaport District
Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.





View properties in map for Beacon Hill
Beacon Hill
Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.





View properties in map for North End
North End
Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.