Bayside Vacations from $673
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Bayside Vacation
Our Bayside vacation packages are an easy and handy way to plan and reserve your next break. Experience the magic of this unique neighborhood without the burden of having to plan everything yourself. Some top nearby attractions to see during your trip to Bayside include Nantasket Beach Reservation, World’s End and Hull Lifesaving Museum. Expedia can help turn your dream Bayside vacation into reality, whatever your travel plans or budget.
The Latest Bayside Vacation Packages
Four Seasons Hotel Boston
Reviewed on Oct 6, 2026
Raffles Boston
Reviewed on Oct 14, 2026
Where to stay in Bayside
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.
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.
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.
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.
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.
Bayside Hotel Deals
Omni Boston Hotel at the Seaport
The Revolution Hotel
"Second time staying here - was in a double room last time with a friend and that was great - the single room very tight - the sink too small to really use without getting water all over. no chair or luggage rack. Clean and sparse. Liked that they had a small gym downstairs. Nice area & close to Boston ..."
Reviewed on Oct 15, 2026
Seaport Hotel Boston
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
Boston Haunted Tour : Ghosts & Gravestones
