Assembly Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    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

Top Holiday Package Deals in Assembly Square

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,643, price is now CA $1,156 per person
CA $1,156
per person
Dec 15 - Dec 18
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,564, price is now CA $1,227 per person
CA $1,227
per person
Dec 24 - Dec 27
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,478, price is now CA $1,614 per person
CA $1,614
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,449, price is now CA $1,686 per person
CA $1,686
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Great hotel and a great team

Reviewed on Nov 1, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was CA $1,581, price is now CA $1,191 per person
CA $1,191
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (4,278 reviews)

Where to stay in Assembly Square

Find the best Assembly Square areas and neighborhoods for the activities you enjoy most. Learn more about Assembly Square
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

Assembly Square Hotel Deals

La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Dec 6 to Dec 7
CA $126
CA $140 total
Dec 6 - Dec 7
includes taxes & fees
7.4/10 Good! (3,576 reviews)
"La habitación tenía un olor desagradable"

Reviewed on Nov 5, 2026

La Quinta Inn & Suites by Wyndham Boston Somerville
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 $195 per night from Nov 22 to Nov 23
CA $195
CA $284 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (4,986 reviews)
"I had an excellent stay at the Omni Hotel in Seaport Boston. The rooms were spotless and comfortable, and the staff was friendly and attentive. Highly recommend for a relaxing and enjoyable stay."

Reviewed on Nov 5, 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 CA $148 per night from Nov 25 to Nov 26
CA $148
CA $172 total
Nov 25 - Nov 26
includes taxes & fees
The Revolution Hotel
See all 3,990 properties in Assembly Square
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 an Assembly Square vacation package cost?
Get your credit card ready, because a trip to Assembly Square starts from an affordable CA $1,156. When you bundle your flights, hotels and more into a travel package, you'll land the best bargains.
How do I get a cheap travel package to Assembly Square?
Booking an Assembly Square vacation package with Expedia is one of the easiest ways to save. We have access to more than 550 air carriers and 1,000,000 properties globally. With such an amazing range to choose from, you'll have no hassles pulling together your ideal getaway.
Where should I stay in Assembly Square?
A getaway to Assembly Square isn't complete without stopping by Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Spend your nights near these top attractions and make sightseeing easy.
What are the top hotels in Assembly Square?
If it's your first time in Assembly Square, lock in a room at The Row Hotel at Assembly Row, Autograph Collection or La Quinta Inn & Suites by Wyndham Boston Somerville. Both offer friendly service and are top options with many travelers.
How far in advance should I book my Assembly Square vacation?
To bag discount prices, book ASAP. Airlines usually start selling tickets, along with some of the lowest fares, up to 12 months in advance. Hotels, car rental and activities should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway to Assembly Square, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Assembly Square travel package include?
That depends on what you're looking for. If you're traveling by yourself, you might decide to bundle flights and hotels. Bringing the whole crew to Assembly Square? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the flexibility to tailor-make your travel package.
What should I know before booking an Assembly Square travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've created your package, add on fun stuff like activities or tours. Your next awesome vacation is only a few clicks away.
Can I choose my airline with an Assembly Square Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You get to choose. We have access to more than 550 airline partners across the globe, so you have options galore when putting together your Assembly Square trip.
If I'm not able to travel, can I cancel my Assembly Square vacation package?
Your situation can change without warning, so yes. You may be able to cancel or amend your Assembly Square vacation package at no cost within 24 hours of booking. For bookings older than that, you can still make changes, but your hotel, car rental company or airline may impose a charge. Looking for more information? Have a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Stay near popular Assembly Square attractions

Assembly Row

9.2/10 (414 reviews)
You can find the perfect gifts to bring home at Assembly Row during your visit to Somerville.
See properties

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Museum of Ice Cream Boston Admission Ticket

Museum of Ice Cream Boston Admission Ticket

CA $62
per adult
80% of travellers recommend
Museum of Ice Cream Boston Admission Ticket
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.