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.
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,300, price is now CA $878 per person
CA $878
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year
Reviewed on Jun 18, 2026
Boston Harbor Hotel
North End
Price was CA $2,637, price is now CA $1,652 per person
CA $1,652
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026
Chatham Tides
Price was CA $2,824, price is now CA $1,924 per person
CA $1,924
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (707 reviews)
It was absolutely charming and beautiful! The view was magnificent, the staff couldn't have been more accommodating and the room was wonderful. I would return to Room 23 over and over again.
Reviewed on Jun 20, 2026
Luxury Apartments by Hyatus at Boston Everett
Price was CA $1,578, price is now CA $1,147 per person
CA $1,147
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (4 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week.
We did not have a rental car but the parking garage was easily accessible and secure.
We were able to get ubers very easily from the location.
The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient.
The support staff replied to all our messages in the chat option quickly and were very helpful.
The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred.
Would recommend this place without hesitation.
Reviewed on Jun 15, 2026
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
Downtown Boston
4.5/5(197 area reviews)
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.
Medford Hillside Hotel Deals
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jun 30 to Jul 1
CA $203
CA $236 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (2,685 reviews)
"So appreciated the creativity in the design and layout. The bed was comfortable, the bathrooms clean, and the suggestions for lunch were great! Staff were friendly and helpful too.The coffee and tea bar were outstanding too. We took advantage of the Mexican restaurant and bar as well. Perfect place ..."
Reviewed on Jun 20, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $293 per night from Jul 2 to Jul 3
CA $293
CA $399 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (4,722 reviews)
"T"
Reviewed on Jun 21, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Jul 5 to Jul 6
CA $268
CA $360 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (4,456 reviews)
"Très bien situé à seaport"
Reviewed on Jun 21, 2026
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.
Discover the most popular places to visit in Medford Hillside
Fenway Park
4.5/5(310 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
4.5/5(28 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.
Harvard University
4.5/5(284 reviews)
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $73
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.