South Boston Vacation Packages

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Save up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in South Boston

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

Battery Wharf Hotel, Boston Waterfront

North End

CA $764

per person

Jan 8 - Jan 10

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9/10 Wonderful! (2,071 reviews)

The hotel grounds are extremely well maintained; the views of the water and benches to relax on are fantastic! We had a great stay with our two teenagers. It was out of the hustle and bustle of the city. A wonderful place!

Reviewed on Oct 26, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

CA $982

per person

Dec 11 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,004 reviews)

Excellent as always.

Reviewed on Oct 27, 2026

Raffles Boston

Back Bay

Save 100% on your flight

CA $935

per person

Jan 8 - Jan 10

found 6 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.6/10 Exceptional! (343 reviews)

设施很新，SPA桑拿体验特别好，晚餐气氛很棒

Reviewed on Oct 20, 2026

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

CA $1,817

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (487 reviews)

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

CA $1,676

per person

Nov 26 - Nov 29

found 2 days ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (465 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 $258

CA $357 total

Nov 26 - Nov 27

includes taxes & fees

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $190

CA $269 total

Nov 26 - Nov 27

includes taxes & fees

9.6/10 Exceptional! (5,160 reviews)

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Reviewed on Oct 26, 2026

YOTEL Boston, Select by Hilton

65 Seaport Blvd Boston MA

Fully refundableReserve now, pay when you stay

CA $164

CA $264 total

Nov 26 - Nov 27

includes taxes & fees

8.8/10 Excellent! (2,658 reviews)

"The room was very small. Kinda like a room on a cruise ship. Not worth the price."

Reviewed on Oct 27, 2026

See all 1,427 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 $764. 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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