Highland Park Vacation Packages

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Top Holiday Package Deals in Highland Park

Price found within the past 48 hours. Click for updated prices.
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Price was CA $1,375, price is now CA $868 per person
CA $868
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,253, price is now CA $2,177 per person
CA $2,177
per person
Apr 22 - Apr 27
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,499, price is now CA $1,015 per person
CA $1,015
per person
Mar 26 - Mar 30
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Nice hotel. Good front desk reception. Great location.

Reviewed on Feb 19, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $3,258, price is now CA $2,213 per person
CA $2,213
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,335, price is now CA $2,307 per person
CA $2,307
per person
Apr 25 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Everything. Location of hotel is great. Hotel is clean. Staff is polite and at your service at all times. Very accommodating to your needs and make you feel at home.

Reviewed on Feb 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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Mar 2 to Mar 3
CA $167
CA $251 total
Mar 2 - Mar 3
includes taxes & fees
8.2/10 Very Good! (3,115 reviews)
Staff, amenities, and perfect location. Wonderful hotel!

Reviewed on Feb 16, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $134 per night from Feb 23 to Feb 24
CA $134
CA $156 total
Feb 23 - Feb 24
includes taxes & fees
9.2/10 Wonderful! (6,288 reviews)
Very large room, it was an inside room so no windows to see outside. Staff was very helpful and friendly

Reviewed on Feb 20, 2026

Harborside Inn Of Boston
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 $166 per night from Feb 22 to Feb 23
CA $166
CA $250 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (4,474 reviews)
I looooove the staff! Excellent hotel and for the price too! We loved it soo much looking to visit again soon.

Reviewed on Feb 16, 2026

Omni Boston Hotel at the Seaport
See all 4,177 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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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 $868. 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 featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

4.5/5(27 reviews)

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

Gillette Stadium
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
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 $108
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $31
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.