Central 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

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

Top Holiday Package Deals in Central 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

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,666, price is now CA $1,048 per person
CA $1,048
per person
Aug 2 - Aug 7
found 2 days ago
Roundtrip flight included
Toronto (YTO) 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 $1,300, 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

Where to stay in Central Square

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

Central Square Hotel Deals

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! (2,371 reviews)
"Thank you for putting up with the Scottish fans. What a wonderful welcoming you have given us."

Reviewed on Jun 18, 2026

Hyatt Regency Boston/Cambridge
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 $293 per night from Jul 2 to Jul 3
CA $293
CA $399 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (4,721 reviews)
"T"

Reviewed on Jun 21, 2026

Omni Boston Hotel at the Seaport
See all 4,105 properties in Central 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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Family Vacations
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Frequently asked questions

How much does a Central Square vacation package cost?
Be ready to book, because a trip to Central Square starts from a tempting CA $841. When you combine your flights, hotels and car rentals into a travel package, you'll pick up the lowest prices.
How do I get a cheap travel package to Central Square?
Find flights that suit your busy schedule, add a hotel to your booking and watch how much you save with a Central Square vacation package. It's as simple as that! From hotels and flights to rental cars and activities, Expedia is where your cheap getaway begins. And with more than 550 airlines and 1,000,000 properties across the globe to pick from, you won't be short of choice.
Where should I stay in Central Square?
Make sightseeing easier by staying someplace right around the corner from Central Square's big attractions. Harvard Square and Massachusetts Institute of Technology are two which top many visitors' bucket lists.
What are the top hotels in Central Square?
The Windsor Inn and Cambridge Urban Oasis Apartment Betw M. I. T. And Harvard are two of the most well-known properties in Central Square. Why not have a look at the rates and facilities at each and then make up your mind?
How far in advance should I book my Central Square vacation?
While prices do change, we generally advise booking your flight as soon as possible. Most international airfares become available on Expedia up to a year in advance. If you're booking last minute, you might still get lucky. Cheap journeys to Central Square sometimes appear only weeks before departure.
What does an Expedia Central Square travel package include?
It comes down to what kind of trip you're thinking about. Central Square vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits you. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking a Central Square travel package?
Find deals to match your budget with an Expedia package. Flights, hotels, rental cars — we've got them all. You'll save a packet just for bundling your bookings. Whether you're taking off on a snow and ski adventure or kicking back on a warm beach, your ideal getaway is only clicks away.
Can I choose my airline with a Central Square Expedia vacation package?
With a vacation package, you're in control. Whether you're eager to fly to Central Square in economy or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Central Square vacation package?
We get that unexpected stuff happens. If you've locked in a Central Square vacation package and need to change or cancel it, we're here to help. We suggest checking out our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to change your itinerary for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

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 $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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
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.