South Boston Vacation Packages

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Top Holiday Package Deals in South Boston

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

Boston Lodge and Suites

Dorchester

CA $656

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Boston (BOS)

8.4/10 Very good! (194 reviews)

The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Mandarin Oriental, Boston

Back Bay

CA $1,717

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Boston (BOS)

9.4/10 Exceptional! (465 reviews)

Four Seasons Hotel Boston

Bay Village

CA $1,679

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Boston (BOS)

9.4/10 Exceptional! (491 reviews)

Boston Harbor Hotel

North End

CA $1,418

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

9.8/10 Exceptional! (1,004 reviews)

Lovely for a romantic stay

Reviewed on Oct 31, 2026

Raffles Boston

Back Bay

CA $1,506

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Boston (BOS)

9.6/10 Exceptional! (343 reviews)

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

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.

South Boston Hotel Deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

CA $219

CA $311 total

Nov 22 - Nov 23

includes taxes & fees

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $171

CA $247 total

Nov 23 - Nov 24

includes taxes & fees

YOTEL Boston, Select by Hilton

65 Seaport Blvd Boston MA

Fully refundableReserve now, pay when you stay

CA $183

CA $286 total

Nov 22 - Nov 23

includes taxes & fees

8.8/10 Excellent! (2,652 reviews)

"Amazing location within scenic walking distance of major attractions, nearby transit (free Silver Line bus from the airport), restaurants, coffee, and even a Trader Joe’s behind the hotel which came in handy for fresh fruit/snacks on this trip. Rooms were smaller but I don’t live here so fine for ..."

Reviewed on Oct 31, 2026

See all 1,433 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.

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 $656. 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

A modern architectural building with a large overhanging roof and a glass facade.

Boston Convention and Exhibition Center

8.8/10 (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 fascinating museums or attend a sporting event in this vibrant area.

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