South Boston Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Fenway–Kenmore
Price was S$2,326, price is now S$2,124 per person
S$2,124
per person
9 Feb - 13 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.4/10 Exceptional! (1,839 reviews)
Staff is so welcoming and helpful! We are always leaving with gratitude and a desire to visit again!

Reviewed on 13 Dec, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was S$3,350, price is now S$2,719 per person
S$2,719
per person
9 Feb - 13 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
It was ok noting like the one overseas.

Reviewed on 7 Dec, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was S$2,859, price is now S$2,389 per person
S$2,389
per person
9 Feb - 13 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on 26 Nov, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was S$2,539, price is now S$2,262 per person
S$2,262
per person
9 Feb - 13 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.2/10 Wonderful! (1,196 reviews)
Good, clean, I am satisfied

Reviewed on 3 Dec, 2025

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was S$2,389, price is now S$2,150 per person
S$2,150
per person
9 Feb - 13 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Festive and comfortable beds

Reviewed on 18 Dec, 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 which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in South Boston

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 S$268 per night from 19 Dec to 20 Dec
S$268
19 Dec - 20 Dec
includes taxes & fees
9/10 Wonderful! (4,300 reviews)
Smooth check in

Reviewed on 15 Dec, 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 S$298 per night from 2 Jan to 3 Jan
S$298
2 Jan - 3 Jan, 2026
includes taxes & fees
9.6/10 Exceptional! (3,828 reviews)
Great stay!

Reviewed on 18 Dec, 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 S$215 per night from 23 Dec to 24 Dec
S$215
23 Dec - 24 Dec
includes taxes & fees
9/10 Wonderful! (2,324 reviews)
It was nice, clean, polite, professional. Not kid friendly but it a business hotel. We were heading out on cruise next day so all good.

Reviewed on 13 Dec, 2025

The Westin Boston Seaport District
See all 1,407 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 holiday package cost?
We make it easy to travel somewhere new, with South Boston holiday packages starting from just S$2,124. 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 holiday 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 holiday?
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 holiday 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 holiday 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 holiday 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 holiday 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.

Popular places to visit

Boston Tea Party Ship which includes a bay or harbour and boating

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
Institute of Contemporary Art

Institute of Contemporary Art

Between its striking modern building and its vast collections of contemporary art, this museum on Boston’s waterfront provides delights to enjoy at every turn.

Institute of Contemporary Art
Seaport World Trade Center

Seaport World Trade Center

Seaport World Trade Center is just one of the places to see in Boston, so why not enjoy the other things to explore during your travels? Stroll along the waterfront or attend a sporting event in this vibrant area.

Seaport World Trade Center

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$102
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

S$40
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

S$109
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.