Highland Park Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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Top Holiday Package Deals in Highland Park
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $813
per person
Oct 21 - Oct 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Where to stay in Highland Park
Find the best Highland Park areas and neighborhoods for the activities you enjoy most. Learn more about Highland Park
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
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.
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.
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.
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.
Highland Park Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $263
CA $353 total
Aug 30 - Aug 31
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $189
CA $220 total
Aug 25 - Aug 26
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $305
CA $411 total
Aug 30 - Aug 31
includes taxes & fees
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.
Frequently asked questions
How much does a Highland Park vacation package cost?
Get set to book, because a trip to Highland Park starts from only CA $813. When you bundle your hotels, flights and car rentals into a package, you'll land the best prices.
How do I get a cheap travel package to Highland Park?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you a few dollars too. A Highland Park vacation package makes it simple to arrange your dream adventure. With more than 550 airlines worldwide to pick from, finding flights that fit your schedule will be no sweat. Not only that, we've got over 1,000,000 hotels globally to pick from. Now that's what you call choice. No matter who you are, Expedia will help show you the world.
Where should I stay in Highland Park?
Visitors come from every corner of the globe to see Fenway Park and TD Garden in Highland Park. Stay within walking distance of these fantastic attractions to make sightseeing easy.
What are the top hotels in Highland Park?
Whether you'll be staying for a night or a week in Highland Park, you'll get a great night's sleep at Fort Hill Inn - Boston Cozy, L@@k Comfortable. This option is a favorite with plenty of travelers.
How far in advance should I book my Highland Park vacation?
While not all air carriers advertise tickets early, customers are usually able to start comparing international airfares on Expedia up to 12 months in advance. This is the time you can nab some incredible bargains. If you're booking late, you might still be in luck. Low prices sometimes become available a few weeks before departure.
What does an Expedia Highland Park travel package include?
Flights, hotels and rental cars — we have them covered. With Expedia, you can shape your Highland Park travel package just how you like it. All you have to do is decide just what you need. Once you've made your booking, you can add extras like tours and activities. The more you bundle, the bigger your savings!
What should I know before booking a Highland Park travel package?
Whether it's adventure or relaxation you're chasing, a Highland Park vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Highland Park Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You get to decide. We have more than 550 partner airlines globally, so you have loads of choice when arranging your Highland Park escape.
If I'm not able to travel, can I cancel my Highland Park vacation package?
We get it — sometimes life doesn't go according to plan. If you've booked a Highland Park vacation package and need to change or cancel it, we can help. We recommend checking out our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a fee.
Stay near popular Highland Park attractions
Dillaway-Thomas House
You can spend an afternoon studying the exhibits at Dillaway-Thomas House during your travels in Boston. Take in the museums while you're in the area.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
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.