High Street Hill Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Jul 16 - Jul 30

    The Atlas Hotel + Flight

    Allston
    14 nights
    4.5 star property
    9.4/10 - Exceptional (122 reviews)
    "Generally great, but parking is an issue. No validation for the garage next to the hotel, all-day full price for a 2-3 hour park on Sunday. They said they’re working on it- the hotel has only been open 4 months. Location good- close enough to walk to Harvard Square (a longish walk), short drives to most places in Boston (if you’re not from the area, you’ll need really good GPS- the streets are notoriously difficult to negotiate, and rightfully so). The restaurant was excellent (pricey) and the..."
    Reviewed May 30, 2026
    Return • Auckland (AKL) - Boston (BOS)
    AKL - BOS • 1 stop BOS - AKL • 1 stop
    NZ$7,103
    NZ$5,127
    per traveller
    found 19 hours ago
    The Atlas Hotel
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Jul 16 - Jul 30

    Boston Harbor Hotel + Flight

    North End
    14 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Boston (BOS)
    AKL - BOS • 1 stop BOS - AKL • 1 stop
    Save 100% on your flight
    NZ$16,104
    NZ$9,163
    per traveller
    found 19 hours ago
    Boston Harbor Hotel
  • Front of property
    Jul 16 - Jul 30

    Eurostars The Boxer + Flight

    West End
    14 nights
    4.0 star property
    8.8/10 - Excellent (1,509 reviews)
    "For the price they charge, it’s not worth it"
    Reviewed June 1, 2026
    Return • Auckland (AKL) - Boston (BOS)
    AKL - BOS • 1 stop BOS - AKL • 1 stop
    NZ$9,695
    NZ$6,691
    per traveller
    found 19 hours ago
    Eurostars The Boxer
  • 3 restaurants; breakfast, lunch, dinner and brunch served
    Jul 16 - Jul 30

    The Charles Hotel + Flight

    West Cambridge
    14 nights
    4.0 star property
    9.4/10 - Exceptional (1,001 reviews)
    "Fantastic Hotel. Loved the location, room was clean, staff was helpful, and loved the amenities."
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Boston (BOS)
    AKL - BOS • 1 stop BOS - AKL • 1 stop
    Save 100% on your flight
    NZ$14,203
    NZ$10,084
    per traveller
    found 19 hours ago
    The Charles Hotel
  • Exterior
    Jul 16 - Jul 30

    Luxury 2BR near Cambridge + Flight

    Prospect Hill
    14 nights
    3.0 star property
    8.0/10 - Very good (1 review)
    "Great apartment but the building's main door was malfunctioning and we could only get in when a resident with a key entered/exited. Also the wifi didn't work. The provider sis not offer any support or compensation, otherwise this would have been a perfect stay."
    Reviewed March 27, 2026
    Return • Auckland (AKL) - Boston (BOS)
    AKL - BOS • 1 stop BOS - AKL • 1 stop
    NZ$9,084
    NZ$6,475
    per traveller
    found 19 hours ago
    Luxury 2BR near Cambridge

Our guide on where to stay in High Street Hill

Find the best High Street Hill areas and neighborhoods for the activities you enjoy most. Learn more about High Street Hill
Downtown Boston

Downtown Boston

4.5/5(17 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Our pick of the best High Street Hill Hotel Deals

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 NZ$507 per night from 7 June to 8 June
NZ$507
7 June - 8 June
includes taxes & fees
9.2/10 Wonderful! (4,676 reviews)
"Very disappointed in the aesthetics of the room in the artist tower. It felt awful waking up in the morning and looking at a concrete ceiling that looked unfinished. And also the corner pillars that were concrete and unfinished.There was no luggage rack to put your suitcase on and no closets. It ..."

Reviewed on 1 June 2026

Omni Boston Hotel at the Seaport
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 NZ$269 per night from 7 June to 8 June
NZ$269
7 June - 8 June
includes taxes & fees
9/10 Wonderful! (2,639 reviews)
"A unique hotel that we enjoyed. Very clean."

Reviewed on 31 May 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is NZ$563 per night from 28 June to 29 June
NZ$563
28 June - 29 June
includes taxes & fees
9.6/10 Exceptional! (4,402 reviews)
"This property is perfect! My only complaint is that when I booked it stated that we would have free breakfast and upon arrival they stated that we did not have breakfast included in our stay. Pretty disappointed but it did not take away from the beauty and cleanliness at this hotel"

Reviewed on 1 June 2026

Seaport Hotel Boston
See all 4,095 properties in High Street Hill
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 High Street Hill holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in High Street Hill from just . And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to High Street Hill?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into a High Street Hill holiday package to save loads of cash. Score even more bargains when you include extras such as activities or tours to your booking. But that's not the only good part. You have the flexibility to tailor your trip your way. We offer more than 550 airlines and 1 000 000 properties all over the world, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in High Street Hill?
We recommend staying near the action. Many people favor hotels in the vicinity of popular attractions, such as Coolidge Corner Theatre, John Fitzgerald Kennedy National Historic Site and Larz Anderson Auto Museum.
How far in advance should I book my High Street Hill holiday?
It can be difficult to know when is the ideal time to book your High Street Hill holiday. But usually the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels nearly 12 months before your departure date. If you're hoping for a last-minute getaway, no need to stress! There are unbeatable bargains posted on Expedia every single day.
What does an Expedia High Street Hill travel package include?
That depends on what type of escape you have in mind. High Street Hill travel deals can include flights, hotels and car rentals. You can mix and match to create the bundle that works for you! You can also add on activities and experiences after you've booked to get even bigger discounts.
What should I know before booking a High Street Hill travel package?
So many places to venture to, so many things to do. With a package, you'll be able to afford more of them. Bundle your flights, hotels and rental cars and get set to save.
Can I choose my airline with a High Street Hill Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my High Street Hill holiday package?
You can. We realise even the best-laid plans can fail, so we're happy to help if you have to make changes to your High Street Hill holiday package. You may be able to cancel or change your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in High Street Hill

Fenway Park

Fenway Park

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

Fenway Park
Harvard University

Harvard University

You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.

Harvard University
Gillette Stadium

Gillette Stadium

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

Gillette Stadium

Activities

Boston Hop-On Hop-Off Trolley Tour

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

NZ$97
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

NZ$60
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Whale Watching Tour

Whale Watching Tour in Gloucester

NZ$80
per adult
98% of travellers recommend
Whale Watching Tour in Gloucester
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.