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

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,062, price is now CA $590 per person
CA $590
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,022, price is now CA $1,680 per person
CA $1,680
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug. 24, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,949, price is now CA $1,804 per person
CA $1,804
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Motel 6 Danvers, MA - Boston North

Motel 6 Danvers, MA - Boston North

2 out of 5
Price was CA $1,467, price is now CA $979 per person
CA $979
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
5.2/10 (1,003 reviews)
Nice family-friendly property with plenty of soap & towels

Reviewed on Aug. 24, 2025

Bay Village Suites

Bay Village Suites

2 out of 5
Bay Village
Price was CA $1,322, price is now CA $901 per person
CA $901
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
6.4/10 (191 reviews)
Excellent value for the price! I recommend it highly. More amenities in the rooms than they list online, including microwave, mini fridge, coffee, toaster, iron, hair dryer, some clothes hangers. Soap, shampoo and conditioner in the shower. Comfy and clean bed. A charming old brownstone.

Reviewed on Aug. 24, 2025

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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 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

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $249 per night from Sep 1 to Sep 2
CA $249
CA $347 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,840 reviews)
"Overall a great hotel. Well located, the seaport zone is really beautiful. Public transportation access"

Reviewed on Aug. 21, 2025

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 1 to Sep 2
CA $207
CA $248 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,259 reviews)
"We liked that the beds were comfortable and the AC was quiet. The food at the hotel was delicious. The pool was also very nice."

Reviewed on Aug. 22, 2025

Seaport Hotel Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
425 Summer St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Sep 1 to Sep 2
CA $275
CA $368 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (2,118 reviews)
"Great location, excellent customer service, $50 meal vouchers, clean, comfortable accommodations, Starbucks, indoor pool/hot tub and a short walk to the seaport!!"

Reviewed on Aug. 24, 2025

The Westin Boston Seaport District
See all 1,342 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $590. 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.

Discover the most popular places to visit in South Boston

Boston Tea Party Ship featuring boating and a bay or harbour

Boston Tea Party Ship

Come to this museum and the three historic ships in the Boston Harbor to relive the momentous events of the Boston Tea Party.

Boston Tea Party Ship
Castle Island

Castle Island

The ancient Fort Independence finds its home on this impressive harbor peninsula, a beautiful place to walk and relax along the waterfront.

Castle Island
Columbus Park

Columbus Park

Explore the great outdoors at Columbus Park, a lovely green space in Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.

Columbus Park

Things to do

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Spirit of Boston Signature Lunch Cruise

CA $133
per adult
Spirit of Boston Signature Lunch Cruise
Spirit of Boston cruise ship at night

Spirit of Boston Signature Dinner Cruise

CA $267
per adult
Spirit of Boston Signature Dinner Cruise
Classic Tall Ship Cruise in Boston Harbor

Classic Tall Ship Cruise in Boston Harbor

CA $48
per adult
100% of travellers recommend
Classic Tall Ship Cruise in Boston Harbor
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.