Assembly Square Vacation Packages

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Top Holiday Package Deals in Assembly Square

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,558, price is now CA $841 per person
CA $841
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,637, price is now CA $1,652 per person
CA $1,652
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,300, price is now CA $878 per person
CA $878
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year

Reviewed on Jun 18, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,824, price is now CA $1,924 per person
CA $1,924
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (707 reviews)
It was absolutely charming and beautiful! The view was magnificent, the staff couldn't have been more accommodating and the room was wonderful. I would return to Room 23 over and over again.

Reviewed on Jun 20, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $1,578, price is now CA $1,147 per person
CA $1,147
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (4 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 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 $183 per night from Jun 30 to Jul 1
CA $183
CA $204 total
Jun 30 - Jul 1
includes taxes & fees
7.6/10 Good! (3,372 reviews)
"Only complaint is strong distasteful odor when room door was first opened. Seemed to dissipate after a few minutes. Other than that everything was satisfactory. Staff were excellent"

Reviewed on Jun 20, 2026

La Quinta Inn & Suites by Wyndham Boston Somerville
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 $203 per night from Jun 30 to Jul 1
CA $203
CA $236 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (2,685 reviews)
"So appreciated the creativity in the design and layout. The bed was comfortable, the bathrooms clean, and the suggestions for lunch were great! Staff were friendly and helpful too.The coffee and tea bar were outstanding too. We took advantage of the Mexican restaurant and bar as well. Perfect place ..."

Reviewed on Jun 20, 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 5 to Jul 6
CA $203
CA $277 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,372 reviews)
"Great stay, only one thing let this hotel down was tried to have breakfast and they couldn’t give us a table even although there were many empty tables. Suggested we went on a waiting list but then couldn’t guarantee we would get a table before breakfast finished!"

Reviewed on Jun 21, 2026

Hyatt Regency Boston/Cambridge
See all 4,082 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
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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 $841. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.