A cityscape with a rainbow and clouds.

Hyde Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Hyde Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 29 - Feb 1

    Encore Boston Harbor + Flight

    Everett
    3 nights
    5.0 star property
    9.6/10 - Exceptional (4,354 reviews)
    "good"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,440
    CA $1,084
    per traveller
    found 6 hours ago
    Encore Boston Harbor
  • Jan 29 - Feb 1

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (497 reviews)
    "The best location and the beat service! The best swimming pool"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,361
    CA $1,525
    per traveller
    found 6 hours ago
    Four Seasons Hotel Boston
  • Dec 26 - Dec 30

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,007 reviews)
    "All the staff was very helpful and responsive I would recommend this hotel to everyone planning to stay in Boston."
    Reviewed November 9, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    Save 100% on your flight
    CA $3,007
    CA $2,012
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Jan 29 - Feb 1

    Raffles Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (355 reviews)
    "Great place to stay!!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,311
    CA $1,581
    per traveller
    found 6 hours ago
    Raffles Boston
  • Jan 29 - Feb 1

    The Newbury Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (749 reviews)
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • 1 stop
    CA $1,841
    CA $1,321
    per traveller
    found 1 day ago
    The Newbury Boston

Where to stay in Hyde Square

Find the best Hyde Square areas and neighborhoods for the activities you enjoy most.

Downtown Boston

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.

Back Bay

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

Seaport District

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

Beacon Hill

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Hyde Square Hotel Deals

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 Hyde Square vacation package cost?

Our Hyde Square packages, which start from as low as CA $1,084, are an awesome way to save big. Select your favorite hotels, flights and rental car to create a personalized escape.

How do I get a cheap travel package to Hyde Square?

Our Hyde Square vacation packages offer plenty of savings for the savvy globetrotter. For the best deal, simply bundle your flights, hotels and rental cars into a neat and tidy package. But great bargains are only the start of your next memorable adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels around the world to choose from. Whatever your budget or style, there's a package with your name on it.

Where should I stay in Hyde Square?

Most travelers who visit Hyde Square include both Fenway Park and TD Garden on their bucket lists. Why not consider a hotel as close as possible to these popular attractions?

What are the top hotels in Hyde Square?

Stunning Renovated Sunny 1400sf 4 Bedroom Victorian Style Apartment Free Parking and Wyman Bed And Breakfast are a couple of the most popular hotels in Hyde Square. Why not take a look at the amenities and facilities at each and then decide?

How far in advance should I book my Hyde Square vacation?

Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to 12 months prior to departure dates. This is typically the cheapest time to book. If circumstances have left you booking late, low prices to Hyde Square sometimes occur just a few weeks before departure.

What does an Expedia Hyde Square travel package include?

Rental cars, hotels and flights, or any combination of the three — you decide! Whether you're exploring Hyde Square with the entire family or traveling solo, there's a package to fit your budget and style. Once you've made your booking, why not add on a few tours or activities?

What should I know before booking a Hyde Square travel package?

Bundling your bookings into a Hyde Square vacation package is the easiest way to organize your trip. Not only that, you'll get great discounts when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?

Can I choose my airline with a Hyde Square Expedia vacation package?

Yes — that's the beauty of an Expedia vacation package. You can mix and match your flights, hotels and more. We have access to more than 550 airline partners globally, so you have loads of choice when planning your Hyde Square getaway.

If I'm not able to travel, can I cancel my Hyde Square vacation package?

Because we understand life can be unpredictable, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've booked your Hyde Square vacation package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.

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