Leather District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

Top Holiday Package Deals in Leather District

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The staff is excellent, especially in the restaurants. The food was great and the bed was very comfortable. The AC in both rooms worked well and everything was clean.

Reviewed on Jul. 14, 2025

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
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Location is perfect. A lots of places to see within walking distance and good restaurants nearby too. The service is great. Friendly and professional staff. The room is clear and spacious. The gym is very big with all the equipments and have personal training rooms too. We stayed 5 nights and were very lucky to get room on 16th floor with a balcony!

Reviewed on Jul. 14, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Awesome stay with everything you need

Reviewed on Jul. 13, 2025

Where to stay in Leather District

Find the best Leather District areas and neighborhoods for the activities you enjoy most. Learn more about Leather District
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 hotels in Downtown Boston

Leather District Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $393 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,667 reviews)
"The hotel was clean and staff was friendly."

Reviewed on Jul. 12, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
The price is CA $252 per night from Jul 20 to Jul 21
CA $252
CA $293 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"Always a great stay"

Reviewed on Jul. 11, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $282 per night from Jul 20 to Jul 21
CA $282
CA $329 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (5,322 reviews)
"This is THE place to stay in Boston, the area is close to everything, the staff at the front desk and the restaurant Joia were beyond efficient and friendly, and although they didn't offer room service, they were more than accommodating to provide water, etc. for the room on the way up to to the ..."

Reviewed on Jul. 13, 2025

Harborside Inn Of Boston
See all 3,701 properties in Leather District
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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Leather District vacation package cost?
From just CA $631. Yes, you read that correctly. Our Leather District packages are an easy way to make your budget stretch further. Combine your flights, hotels and rental car and get to know this popular destination.
How do I get a cheap travel package to Leather District?
Our Leather District vacation packages promise plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and activities into a budget-friendly package. But great bargains are just the beginning of your next epic adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotels globally to select from. Whatever your budget, there's a package that's perfect for you.
Where should I stay in Leather District?
Most people who travel to Leather District put both Fenway Park and TD Garden on their must-see lists. Why not book a hotel that's close to these great attractions?
How far in advance should I book my Leather District vacation?
It all depends on the airline, but you can generally browse through international fares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky customers will occasionally find a cheaper seat just weeks prior to the date of departure.
What does an Expedia Leather District travel package include?
Choose from a combination of rental cars, flights and hotels. Once you've made your booking, you can also add on tours and experiences. Want to pick your airfare class? That's possible too. The choice is all yours when it comes to crafting your ideal Leather District trip.
What should I know before booking a Leather District travel package?
You can save a tidy sum by combining your hotels, flights and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Leather District Expedia vacation package?
You sure can. Expedia has access to more than 550 airline partners across the globe, so fly with the carrier that fits your budget and traveling style.
If I'm not able to travel, can I cancel my Leather District vacation package?
Whether it's your hotel or flight, yes, you can cancel or amend it. Locked in your Leather District vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings made more than 24 hours ago, you may be charged a fee by your airline, hotel or car rental company. For more details, visit our Customer Service Portal. We're here to help you every step of the way.

Discover the most popular places to visit in Leather District

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

Fenway Park

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

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

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

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 CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $46
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.