South Side Holidays from £593

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Your South Side Holiday

Your next big adventure is calling your name with a holiday package to South Side. Relaxation, entertainment and nothing but good times — you're sure to find it in this neighbourhood. When it's time to get out and explore, you'll find loads of big-name attractions nearby including Bentley College, Brandeis University and Moody Street Historic District. Visit one, two (or even all!) during your trip to South Side. Stop dreaming and start doing. When you're ready to book your dream holiday to South Side, Expedia is here to help.

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was £845, price is now £593 per person
£593
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
Property was nice and conveniently in Downtown Boston. The standard room is slightly small, but fine for a few day stay. Our TV did not work, the first time they sent someone to fix it and they unplugged it and plugged it back in. Which worked, however the TV would freeze every hour if not more still and we would have to do the same thing each time. Elevators are slow and there are no stairs to access the hotel rooms.

Reviewed on 19 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,044, price is now £1,209 per person
£1,209
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Save 100% on your flight
Price was £1,053, price is now £715 per person
£715
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,326 reviews)
Great stay as always! Miss the room service coming on actual plates but other than that it was excellent!

Reviewed on 12 Aug 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £2,980, price is now £2,028 per person
£2,028
per person
18 Sept - 25 Sept
found 21 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.4/10 Exceptional! (473 reviews)
Awesome place to stay!

Reviewed on 17 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was £1,498, price is now £1,027 per person
£1,027
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
The beds are the main thing that keep me coming black, so comfortable, especially after a long day of walking around Boston. I will say we were disappointed that the inside of our coffee machine was very dirty.. something i think shouldn't be missed when cleaning since we love a good morning coffee in the room , but had to settle for going to a coffee shop. We tried ordering room service , but after waiting over 1hr we ended up calling to cancel it. For the amount of money we paid , i think they could step their game up when it comes to service and details.

Reviewed on 16 Aug 2025

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Downtown Boston which includes a city and night scenes as well as a small group of people

Downtown Boston

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 Side

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £150 per night from 24 Aug to 25 Aug
£150
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,666 reviews)
"For a small room it was very well laid out. Loved the decor and the staff were very friendly and helpful. We did not have the breakfast but nice to have that option."

Reviewed on 18 Aug 2025

citizenM Boston North Station
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 £143 per night from 1 Sept to 2 Sept
£143
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,248 reviews)
"This was not the least expensive option, but I certainly got what I paid for. People were just so nice. It was easy to get too easy to get around, just perfect."

Reviewed on 17 Aug 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
The price is £212 per night from 1 Sept to 2 Sept
£212
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (3,849 reviews)
It’s okay
"It was cool but the elevator button didn’t work for my floor. There is also a lot of ghetto people enjoying being hood rich for a weekend, be aware."

Reviewed on 18 Aug 2025

Omni Boston Hotel at the Seaport
See all 3,420 properties in South Side
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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(204 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£58
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

£25
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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. Flight-inclusive packages are ATOL protected.