South Medford Vacation Packages

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The Latest South Medford Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A glass-fronted fireplace with visible logs and flames, set on a wooden floor.
    Jan 29 - Feb 1

    Boston Lodge and Suites + Flight

    Dorchester
    3 nights
    4.0 star property
    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 • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,412
    CA $707
    per traveller
    found 1 day ago
    Boston Lodge and Suites
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 29 - Jan 31

    Boston Harbor Hotel + Flight

    North End
    2 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    CA $1,530
    CA $963
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • A brick building with arched windows and a black door, surrounded by greenery and a metal fence.
    Jan 29 - Feb 1

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (496 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YYZ • Nonstop
    CA $2,397
    CA $1,548
    per traveller
    found 1 day ago
    Four Seasons Hotel Boston
  • Pool
    Jan 14 - Jan 17

    Raffles Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (354 reviews)
    "Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    Save 100% on your flight
    CA $2,235
    CA $1,488
    per traveller
    found 1 day ago
    Raffles Boston
  • A park with a lamp post, a bridge, and buildings in the background.
    Jan 14 - Jan 17

    The Newbury Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (747 reviews)
    "Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    Save 100% on your flight
    CA $1,789
    CA $1,298
    per traveller
    found 1 day ago
    The Newbury Boston

Where to stay in South Medford

Find the best South Medford areas and neighborhoods for the activities you enjoy most.
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

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.
A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

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.
A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

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.
A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

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.
A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

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.

South Medford Hotel Deals

A modern building with a courtyard, benches, and flower beds.

Porter Square Hotel

Porter Square Hotel
3.0 star property
2.1 km from South Medford
9.2 out of 10, Wonderful, (1,002 reviews)
"I was only there for a quick weekend wedding trip but the two nights were incredibly comfortable. Everything was clean. I was grateful to have some complimentary coffees available in the morning (and some waters after having a few too many after the wedding). The neighbors were quiet and the staff really did me a solid after I asked for a late checkout. Would absolutely come back."
The price is CA $158
CA $183 total
includes taxes & fees
Nov 22 - Nov 23
Porter Square Hotel
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.
See all properties in South Medford

Frequently Asked Questions

How much does a South Medford vacation package cost?

Get ready to book, because a getaway to South Medford starts from an affordable CA $707. When you bundle your flights, hotels and more into a travel package, you'll score the biggest bargains.

How do I get a cheap travel package to South Medford?

If you love getting an amazing deal, combine your bookings into a South Medford vacation package. Whether you're looking for flights, hotels, activities or rental cars, you can browse and book everything in one place. You'll have loads of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 properties around the globe to take your pick of. Fly with who you want, stay anywhere you like and save your hard-earned money — now that's the perfect vacation!

Where should I stay in South Medford?

Close to the action. Many visitors like to book hotels around popular sights, like Mystic River Reservation, Medford Square and Old Ship Street Historic District.

How far in advance should I book my South Medford vacation?

Reward yourself with the biggest variety at the lowest prices by booking your adventure to South Medford nice and early. Airlines tend to advertise tickets anywhere up to a year in advance, so reserve your spot as soon as you can. Having said that, Expedia is dedicated to providing you with the best deals around, so it's always a good time to book your dream vacation!

What does an Expedia South Medford travel package include?

With Expedia, you can select any combination of car rentals, flights and hotels to build your ideal South Medford travel package. Once you've made your booking, you can add on fun stuff like sightseeing tours and activities. Don't forget — the more you bundle, the more you'll save!

What should I know before booking a South Medford travel package?

You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and pick up great discounts. You're not limited to hotels, though. We've got beachside condos, cabins in the mountains and even houseboats and castles!

Can I choose my airline with a South Medford Expedia vacation package?

You can, and with over 550 airlines to select from worldwide, you have loads of choice. Browse the available options and find out which airline best suits your budget and needs.

If I'm not able to travel, can I cancel my South Medford vacation package?

It's difficult to predict what the future holds, so it's comforting to know that you can cancel or change your South Medford vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to find out more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.