Leather District Vacation Packages

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Top Holiday Package Deals in Leather District

Price found within the past 48 hours. Click for updated prices.
The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $1,046, price is now CA $760 per person
CA $760
per person
Sep 11 - Sep 13
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,007 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,658, price is now CA $2,244 per person
CA $2,244
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $2,130, price is now CA $1,459 per person
CA $1,459
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,464, price is now CA $1,012 per person
CA $1,012
per person
Aug 30 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (197 reviews)
I took my daughter here for her 16th bday. We had such a wonderful time. The rooms were clean, right on the beach, staff super helpful and friendly. We stayed in room 307 and had a view of the ocean. It was the perfect weekend. Will definitely recommend and stay here again.

Reviewed on Jul 27, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $1,992, price is now CA $1,408 per person
CA $1,408
per person
Sep 4 - Sep 7
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (5 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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.

Find hotels in Downtown Boston

Leather District 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 CA $338 per night from Jul 31 to Aug 1
CA $338
CA $451 total
Jul 31 - Aug 1
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
The price is CA $202 per night from Aug 26 to Aug 27
CA $202
CA $235 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (2,782 reviews)
"The shared private bathrooms area is a bit of an adjustment but overall a nice mix. If you're looking for a good place to stay in the Back Bay Area. This is it."

Reviewed on Jul 27, 2026

The Revolution Hotel
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Aug 27 to Aug 28
CA $232
CA $320 total
Aug 27 - Aug 28
includes taxes & fees
9.6/10 Exceptional! (7,407 reviews)
"Top notch hotel walking distance to Quincy market. North end, etc."

Reviewed on Jul 28, 2026

The Dagny Boston
See all 4,164 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 $760. 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.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $39
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $68
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
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.