Assembly Square Vacation Packages

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  • Better together

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

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Top Holiday Package Deals in Assembly Square

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,462, price is now CA $960 per person
CA $960
per person
Jul 3 - Jul 6
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.

Reviewed on May 8, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $2,966, price is now CA $1,944 per person
CA $1,944
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $2,846, price is now CA $1,925 per person
CA $1,925
per person
Jul 27 - Jul 31
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (670 reviews)
Room was clean upon arrival, but there was no "service" daily .... No bed making, no clean towels, no kleenex, etc. We've stayed at Nantucket Inn several time and always like it. We were very disappointed with the daily service this time.

Reviewed on May 8, 2026

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was CA $5,169, price is now CA $3,563 per person
CA $3,563
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (453 reviews)
Top notch. Every member of the staff was a credit to his or her profession.

Reviewed on May 3, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $6,232, price is now CA $4,321 per person
CA $4,321
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (687 reviews)
Will go back very quaint and relaxing

Reviewed on May 8, 2026

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
Downtown Boston

Downtown Boston

4.5/5(197 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

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 $185 per night from May 10 to May 11
CA $185
CA $206 total
May 10 - May 11
includes taxes & fees
7.6/10 Good! (3,330 reviews)
Decent location with plenty of things around. Not much of a lobby specially if you get there early or are to check out a little early - non accommodative - $30 charge for requesting an early checkin (60 minutes prior) and also a charge for later checkout. Had a person sprawled out across 4 chairs ...

Reviewed on May 8, 2026

La Quinta Inn & Suites by Wyndham Boston Somerville
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $421 per night from Jun 5 to Jun 6
CA $421
CA $537 total
Jun 5 - Jun 6
includes taxes & fees
9.6/10 Exceptional! (4,300 reviews)
Excellent

Reviewed on May 8, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is CA $283 per night from May 25 to May 26
CA $283
CA $386 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (4,641 reviews)
Great location. Nice modern room.

Reviewed on May 8, 2026

Omni Boston Hotel at the Seaport
See all 4,155 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
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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 $960. 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.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% 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.