South Boston Holidays

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  • Better together

    Save up to €900 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
  • Standard Room, 1 Queen Bed
    Jul 15 - Jul 24

    Hotel Ivy Boston Common + Flight

    Bay Village
    9 nights
    2.5 star property
    8.4/10 - Very good (1,473 reviews)
    "Rooms are not big but for me traveling solo and going out mostly it was great."
    Reviewed May 31, 2026
    Return • Dublin (DUB) - Boston (BOS)
    DUB - BOS • Direct BOS - DUB • Direct
    Save 100% on your flight
    €2,772
    €1,736
    per traveller
    found 4 hours ago
    Hotel Ivy Boston Common
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Jul 15 - Jul 24

    Boston Harbor Hotel + Flight

    North End
    9 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Boston (BOS)
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    Save 100% on your flight
    €5,172
    €2,931
    per traveller
    found 4 hours ago
    Boston Harbor Hotel
  • Lobby
    Jul 15 - Jul 24

    Fairmont Copley Plaza, Boston + Flight

    Back Bay
    9 nights
    4.5 star property
    9.0/10 - Wonderful (1,244 reviews)
    "I recently stayed at the Fairmont Boston and unfortunately the property felt very outdated and not well maintained compared to what I expected from a Fairmont hotel. While the location is convenient and the staff were generally polite, the overall condition of the hotel needs significant updates. The rooms showed noticeable wear and tear, including older furniture, dated décor, and areas that did not feel particularly clean or refreshed. The hallways and common areas also felt tired and lacked..."
    Reviewed May 29, 2026
    Return • Dublin (DUB) - Boston (BOS)
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    Save 100% on your flight
    €3,638
    €2,389
    per traveller
    found 4 hours ago
    Fairmont Copley Plaza, Boston
  • Indoor pool
    Jul 15 - Jul 24

    Raffles Boston + Flight

    Back Bay
    9 nights
    5.0 star property
    9.6/10 - Exceptional (268 reviews)
    "This was an interesting hotel and if you have any experience of the raffles brand elsewhere then I would recommend be prepared. The venue is central but overlooking an 8storey multi story car park and rather cramp rooms was not really value add. The suite on the other hand in higher floors were. A butler system which I must say working off some mediocre phone prompts just doesn’t cut it . One looses the will to live when saying I need a shaving kit and al you get back is “is there something else..."
    Reviewed May 28, 2026
    Return • Dublin (DUB) - Boston (BOS)
    DUB - BOS • Direct BOS - DUB • Direct
    Save 100% on your flight
    €5,270
    €3,590
    per traveller
    found 4 hours ago
    Raffles Boston
  • Front of property
    Jul 15 - Jul 24

    Eurostars The Boxer + Flight

    West End
    9 nights
    4.0 star property
    8.8/10 - Excellent (1,504 reviews)
    "Front desk staff was very friendly and accommodating"
    Reviewed May 31, 2026
    Return • Dublin (DUB) - Boston (BOS)
    DUB - BOS • Direct BOS - DUB • Direct
    Save 100% on your flight
    €2,853
    €1,953
    per traveller
    found 4 hours ago
    Eurostars The Boxer

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

Downtown Boston

4.5/5(95 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 €258 per night from 7 Jun to 8 Jun
€258
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (4,666 reviews)
"The room was amazing, they put us almost on the top floor, we had an amazing time!"

Reviewed on 31 May 2026

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 €277 per night from 11 Jun to 12 Jun
€277
11 Jun - 12 Jun
includes taxes & fees
9.6/10 Exceptional! (4,397 reviews)
"Clean, updated , friendly staff"

Reviewed on 31 May 2026

Seaport Hotel Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
425 Summer St Boston MA
The price is €219 per night from 7 Jun to 8 Jun
€219
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (2,398 reviews)
"There was a dirty breakfast cart outside our room for the entirety of our stay, by the time we checked out it had gathered a bunch of flies. Not ours"

Reviewed on 1 Jun 2026

The Westin Boston Seaport District
See all 1,478 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 . 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

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
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

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

€45
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

€37
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€72
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 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.