Highland Park Holidays

Book a Hotel + Flight or Car together to unlock savings

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 a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in Highland Park

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
9.2/10 Wonderful! (6,144 reviews)
The staff was so nice and the check-in was easy. It was a nicely decorated boutique hotel that I would definitely stay in again. It was close to absolutely everything; the Freedom Trail, North End, Harbor, Boston Common, and there was a subway station immediately outside of the hotel. The only downside ...

Reviewed on 14 Jan 2026

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Harborside Inn Of Boston
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
The price is 5.788.815 ₫ per night from 17 Feb to 18 Feb
5.788.815 ₫
6.466.107 ₫ total
17 Feb - 18 Feb
includes taxes & fees
9.6/10 Exceptional! (3,507 reviews)
Room was spacious, spotless and comfortable.

Reviewed on 11 Jan 2026

Encore Boston Harbor
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is 3.216.884 ₫ per night from 19 Jan to 20 Jan
3.216.884 ₫
4.534.194 ₫ total
19 Jan - 20 Jan
includes taxes & fees
8.4/10 Very Good! (1,241 reviews)
Check in was great. I'm tall, so I struggle with looking down at name tags. It feels awkward, especially if someone presents as female, I am a male. My check in attendant was helpful, kind, and knowledgeable. I appreciate them, but I didn't catch their name. Maybe at check there could be a nameplate? ...

Reviewed on 12 Jan 2026

Hilton Boston Back Bay
See all 3,954 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.

Frequently asked questions

How much does a Highland Park holiday package cost?
Get set to book, because a trip to Highland Park starts from only . 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 holiday 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 1null000null000 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 Cosy, L@@k Comfortable. This option is a favourite with plenty of travellers.
How far in advance should I book my Highland Park holiday?
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 holiday package lets you organise 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 holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday package?
We get it — sometimes life doesn't go according to plan. If you've booked a Highland Park holiday 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.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Gillette Stadium

Gillette Stadium

3/5(2 reviews)

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

Gillette Stadium
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Harvard University