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Holidays to South Boston

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in South Boston choose Expedia! Find everything you need to organise your trip to South Boston in one place. Enter your dates in the search bar above or scroll to our top deals below!

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

Top Hotel Deals

Cambria Hotel Boston, Downtown-South Boston
Cambria Hotel Boston, Downtown-South Boston
3.5 out of 5
6 West Broadway, Boston, MA
The price is £98 per night from 6 Mar to 7 Mar

This family-friendly Boston hotel is located near the airport, within 2 mi (3 km) of Boston Convention and Exhibition Center, Boston Common and Copley Place. ...

4/5Very Good! (103 reviews)

"Lovely new hotel right in front of the T station. Room was compact, modern, and clean with a nice view (full height window). Limited amenities during the pandemic but there are plenty of local restaurants and cafes in the area (Broadway and South Boston). Downtown Boston, Chinatown, and South End ..."…"

Reviewed on 16 Jan 2021

Cambria Hotel Boston, Downtown-South Boston
★ NEW 3BR ★ Upscale Living For Less!! Walk Boston
★ NEW 3BR ★ Upscale Living For Less!! Walk Boston
142 W 8th St, 2, Boston, MA

Located in South Boston, this holiday home is within 2 miles (3 km) of Boston Convention and Exhibition Center, Boston Children's Museum and Boston Harbor. Black ...

5/5Exceptional! (2 reviews)
Great place

"The apartment was a great place to stay in. It was super nice and the beds were so comfortable. The place was very clean as well. We had some trouble at first trying to get into the place but the property owners were super nice and helped us out. They responded instantly and were very helpful. I ..."…"

Reviewed on 17 Feb 2021

★ NEW 3BR ★ Upscale Living For Less!! Walk Boston
Colbyco D Street - South Boston, MA
Colbyco D Street - South Boston, MA
292 D Street, Unit 3, Boston, MA

Located in South Boston, this condo is within 1 mi (2 km) of World Trade Center and Boston Convention and Exhibition Center. Boston Children's Museum and Black ...

4/5Very Good! (1 review)

"The place met our needs and was in a very convenient location. Within walking distance to local food, shops and bars. The condo was a little smaller than anticipated but bedrooms were decient sized. I recommend bringing extra towels if traveling with a larger group. Entertainment devices for nights ..."…"

Reviewed on 20 Mar 2018

Colbyco D Street - South Boston, MA
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.

Top things to do in South Boston

Plan your South Boston holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in South Boston. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my South Boston holiday package?
If you’ve chosen a South Boston holiday package, you can amend or cancel it, but you may incur a fee in some situations. You may be able to cancel and rebook for free if you’ve taken out your package within 24 hours. If it’s been more than that, you may incur extra charges from your hotel, airline or car rental company. If you suddenly need to change your plans, make our Customer Service Portal your first port of call for more information.
Where should I stay in South Boston?
It makes sense to stay near the action. Many travellers book hotels around popular attractions, such as Boston Public Market, Castle Island and Franklin Park Zoo.
What are the top hotels in South Boston?
Get your trip off to a good start by booking a room at Cambria Hotel Boston, Downtown-South Boston. It’s one of most popular properties in South Boston. Another cosy option is Global Luxury Suites South Boston.
When is the best time of year to visit South Boston?
There’s no right time or wrong time to holiday in South Boston. But if you want to make big savings on your getaway, consider the month of . Hotel rates tend to peak in . South Boston is very popular in , so if you want to escape the crowds, travel in .
How far in advance should I book my South Boston holiday?
Travellers are normally able to browse international flights on Expedia within 12 months of departure. Booking at the last minute? With a bit of luck, it’s still possible to purchase a cheap ticket just weeks before your journey.
What should I know before booking a South Boston travel package?
Tailor deals to match your budget with an Expedia package. Airfares, hotels, rental cars — we’ve got them all. You’ll save precious dollars just by combining your bookings. Whether you’re embarking on a snow and ski adventure or sunning yourself on a warm beach, your perfect getaway is only a few clicks away.
Does Expedia offer Book Now, Pay Later South Boston holiday packages?
If you’d rather spread the cost of your activities and hotel over multiple payments, Expedia can help you out. Paying the total amount for your travel upfront isn’t always the best way to pay for your break, so we’ve joined forces with online lender Affirm to give you financial flexibility. Book Now, Pay Later and remove the stress of saving to travel.