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 Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (217 reviews)
Beautiful room, amenities, service, snacks and coffee station.

Reviewed on May 26, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul. 18 - Jul. 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Great hotel. Very accommodating!

Reviewed on Jun. 6, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
EVERYTHING WAS OUTSTANDING

Reviewed on Jun. 4, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
This is a beautiful hotel with a great gym and first class service. The housekeeping team is world class.

Reviewed on Jun. 5, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (283 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!

Reviewed on May 28, 2024

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 which includes night scenes and a city 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 hotel + flight trips in Downtown Boston

Highland Park Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Jul. 5 to Jul. 6
CA $245
CA $325 total
includes taxes & fees
Jul 5 - Jul 6
9/10 Wonderful! (2,152 reviews)
"The room was very modern, stylish and comfortable."

Reviewed on Jun. 4, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jul. 4 to Jul. 5
CA $232
CA $318 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,687 reviews)
"Had a wonderful stay here and will definitely be a returning guest 😊"

Reviewed on Jun. 5, 2024

Omni Parker House
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 $196 per night from Jun. 16 to Jun. 17
CA $196
CA $228 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,512 reviews)
"Best property to stay at in Boston. Absolutely immaculate. You can walk anywhere from hotel."

Reviewed on Jun. 3, 2024

The Revolution Hotel
See all 3,207 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 $864. 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

Image for Fenway Park

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
Image for Harvard University

Harvard University

4.5/5(279 reviews)

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

Harvard University
Image for Boston Common

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

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $294
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.