Highland Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With 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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,679, price is now CA $1,123 per person
CA $1,123
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
Good for the price. Friendly staff.

Reviewed on May 15, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $4,313, price is now CA $2,603 per person
CA $2,603
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,326, price is now CA $1,523 per person
CA $1,523
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Right in heart of town

Reviewed on May 12, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $3,041, price is now CA $2,020 per person
CA $2,020
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (77 reviews)
Everything was great ! Just not to many options to eat for kids. Had to order out.

Reviewed on May 16, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,990, price is now CA $1,327 per person
CA $1,327
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
clean and great staff

Reviewed on May 8, 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

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.

Find hotels in Downtown Boston

Highland Park Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $318 per night from May 25 to May 26
CA $318
CA $418 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,351 reviews)
Just a fantastic stay in an amazing city. The Seaport is just what you want a hotel to be. Amazing staff , beautiful facility, clean rooms .

Reviewed on May 16, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 24 to May 25
CA $173
CA $202 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (2,609 reviews)
My favorite place to stay in Boston.

Reviewed on May 16, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from May 29 to May 30
CA $246
CA $343 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,647 reviews)
Very big hotel with variety of eating establishments. Early check-in was appreciated. Rooms a very good size. Good place to stay if attending Convention Centre. Hop on hop off bus stops right outside hotel which is handy.

Reviewed on May 17, 2026

Omni Boston Hotel at the Seaport
See all 4,197 properties in Highland Park
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.
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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 $1,123. 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.

Discover the most popular places to visit in Highland Park

Fenway Park

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Gillette Stadium

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $79
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 $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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.