South Boston 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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Top Holiday Package Deals in South Boston

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

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,489, price is now CA $974 per person
CA $974
per person
Aug 13 - Aug 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (125 reviews)
Excellent gym. Brand new and clean. Very Friendly staff. Even a free car charger. Will be back!!

Reviewed on Jun 8, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,532, price is now CA $2,189 per person
CA $2,189
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,000 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $2,120, price is now CA $1,317 per person
CA $1,317
per person
Aug 24 - Aug 29
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (187 reviews)
Such a cute place to stay and the staff are so helpful and welcoming!!

Reviewed on May 31, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,986, price is now CA $1,319 per person
CA $1,319
per person
Aug 13 - Aug 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $2,845, price is now CA $1,929 per person
CA $1,929
per person
Aug 13 - Aug 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (650 reviews)
We loved our one-night stay and wish we could have stayed longer. We had a beautiful park-facing king room on a high floor. The staff was very kind and responsive. The gym is great --- well-equipped and well-maintained. Location could not be better if you plan to explore Boston by foot or the T.

Reviewed on Jun 10, 2026

Where to stay in South Boston

Find the best South Boston areas and neighborhoods for the activities you enjoy most. Learn more about South Boston
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

South Boston 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 $267 per night from Jul 2 to Jul 3
CA $267
per night
Jul 2 - Jul 3
9.2/10 Wonderful! (4,714 reviews)
"Room was TINY — not really a room for two people."

Reviewed on Jun 11, 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $264 per night from Jul 5 to Jul 6
CA $264
per night
Jul 5 - Jul 6
9.6/10 Exceptional! (4,448 reviews)
"Great location, good price, clean and comfortable rooms."

Reviewed on Jun 11, 2026

Seaport Hotel Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
425 Summer St Boston MA
The price is CA $545 per night from Jun 26 to Jun 27
CA $545
per night
Jun 26 - Jun 27
9.2/10 Wonderful! (2,374 reviews)
"The room was beautiful and the staff super friendly and helpful."

Reviewed on Jun 11, 2026

The Westin Boston Seaport District
See all 1,482 properties in South Boston
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.
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Frequently asked questions

How much does a South Boston vacation package cost?
We make it easy to travel somewhere new, with South Boston vacation packages starting from just CA $974. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate getaway, why not add some tours and activities to your travel itinerary?
How do I get a cheap travel package to South Boston?
Browse and book everything in the one place with our South Boston vacation packages. You'll find bargains on flights, hotels, tours and more that'll keep your pocketbook happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 hotel options all over the world to select from, you'll have the flexibility to mix and match your own way.
Where should I stay in South Boston?
Visitors come from near and far to see Fenway Park and TD Garden in South Boston. Book a room close to these must-see attractions to make sightseeing a breeze.
What are the top hotels in South Boston?
Book a stay at Hyatt Place Boston/seaport District. It's one of the area's most sought-after properties. Another top option in South Boston is Omni Boston Hotel at the Seaport.
How far in advance should I book my South Boston vacation?
Your safest bet is to book early. Airlines typically release flights nearly 12 months prior to departure, and this is when you can pick up some of the lowest prices. Boss just told you to use up some vacation time in a few weeks? No need to worry. Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at an affordable price.
What does an Expedia South Boston travel package include?
Flights, rental cars and hotels — you'll discover them all here. With Expedia, you can shape your South Boston travel package just the way you want. All you have to do is work out exactly what you need. Once you've made your booking, you can add extras like activities and experiences. The more you bundle, the bigger the savings!
What should I know before booking a South Boston travel package?
When you book your hotels, flights and car rentals together, you'll score awesome discounts. Whether you're planning a mountain getaway in a cabin or want to stay in an upscale city hotel, Expedia will make it happen for less.
Can I choose my airline with a South Boston Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you definitely can. Simply choose the airline you want and craft your ideal South Boston trip.
If I'm not able to travel, can I cancel my South Boston vacation package?
Because we understand life is full of surprises, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your South Boston vacation package in the last 24 hours, you may be able to change or cancel it without penalty. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.

Stay near popular South Boston attractions

Boston_BostonConventionandExhibitionCenter_6034776_04

Boston Convention and Exhibition Center

4.4/5 (2,207 reviews)
During your trip, find out what's happening at Boston Convention and Exhibition Center, a top convention center in Boston. Experience the acclaimed art scene or attend a sporting event in this vibrant area.
See properties

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.