Medford Hillside Vacation Packages

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Top Holiday Package Deals in Medford Hillside

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

North End
CA $1,356
per person
Nov 28 - Dec 2
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9/10 Wonderful! (2,041 reviews)
Staff was friendly. Had to ask for a microwave but it was brought quickly. Bathroom sliding door wasn’t on the track and didn’t really close, shower tile wasn’t the cleanest… a few times staff just came into our room without announcing themselves. Breakfast buffet was decent but not worth $38 dollars for adults. Hotel food was way overpriced… overall I feel the hotel itself was overpriced for what it is.

Reviewed on Oct 12, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
CA $2,056
per person
Nov 28 - Dec 2
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Great hotel. Loved the health club and pool. Great location. Easy walk to the North End. Comfortable bed. Great service and hospitality.

Reviewed on Oct 13, 2026

The Newbury Boston

The Newbury Boston

Back Bay
Save 100% on your flight
CA $1,785
per person
Nov 26 - Dec 1
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (734 reviews)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
Save 100% on your flight
CA $1,669
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (458 reviews)
The Langham, Boston

The Langham, Boston

Downtown Boston
CA $1,950
per person
Nov 28 - Dec 2
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)

Where to stay in Medford Hillside

Find the best Medford Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Medford Hillside
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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 building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

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 with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

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 street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

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 bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

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.

Medford Hillside Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $376
CA $496 total
Nov 11 - Nov 12
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $184
CA $214 total
Nov 1 - Nov 2
includes taxes & fees
The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $270
CA $363 total
Nov 1 - Nov 2
includes taxes & fees
Seaport Hotel Boston
See all 4,036 properties in Medford Hillside
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.

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $69
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $117
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.