South Boston Vacations from $614
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Your South Boston Vacation
Pick one of our vacation packages to South Boston and immerse yourself in the wonders of this neighborhood. Especially renowned for its festivals, your next great adventure starts right here. Begin your trip to South Boston with a visit to nearby attractions such as Fenway Park, Boston Common and Faneuil Hall Marketplace. Stop daydreaming and start doing. When you're ready to lock in your next vacation to South Boston, Expedia will help you get there.
The Latest South Boston Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts
Price was $867, price is now $614 per person
$614
per person
May 18 - May 22
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (254 reviews)
From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness
The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months -
The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing.
Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take great pride in providing exceptional service, and it made my trip all the more memorable.
Thank you for such a wonderful stay. I will absolutely be recommending your hotel to friends and family, and I look forward to returning in the future.
Reviewed on Mar 29, 2026
D. Hotel Suites & Spa
Price was $1,147, price is now $711 per person
$711
per person
May 29 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
9.2/10 Wonderful! (2,225 reviews)
If you have a kid at one of the five colleges and you are looking for a good place to stay a night or two for a reasonable price, this is a very good option. Nice sized rooms, clean, well maintained and friendly staff.
Reviewed on Apr 5, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was $1,470, price is now $960 per person
$960
per person
Jun 14 - Jun 17
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $3,033, price is now $2,064 per person
$2,064
per person
Jun 11 - Jun 15
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).
Reviewed on Apr 4, 2026
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
4.5/5(2,438 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.
South Boston Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $254 total per night from Apr 10 to Apr 11
$254 total
Apr 10 - Apr 11
Total with taxes and fees
9.2/10 Wonderful! (4,554 reviews)
Staff welcoming, great location for Boston convention center tournament. Clean room and hotel areas.
Reviewed on Apr 5, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $210 total per night from Apr 9 to Apr 10
$210 total
Apr 9 - Apr 10
Total with taxes and fees
9.6/10 Exceptional! (4,133 reviews)
Pros: Convenient location near convention center and Silver Line. Excellent gym. Cons: limited takeout and late night dining options nearby. Destination fee not well disclosed when I made the reservation. Hit my head on the shower door every time I got out.
Reviewed on Apr 5, 2026
YOTEL Boston
65 Seaport Blvd Boston MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $215 total per night from Apr 12 to Apr 13
$215 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (2,461 reviews)
Great location in the Boston Seaport. New and very clean. However, the room was tiny. Not at all like the pictures. If it was a queen bed, she was a small queen. The bartender in the lobby bar was friendly and helpful as were the staff at the registration desk.
Reviewed on Apr 5, 2026
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.
Discover the most popular places to visit in South Boston
Boston Convention and Exhibition Center
4.5/5(747 reviews)
Learn about the events happening at Boston Convention and Exhibition Center during your trip to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.
Flynn Cruiseport Boston
4/5(59 reviews)
Explore the waterfront in Boston with a trip to Flynn Cruiseport Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.
Boston Children's Museum
4.5/5(231 reviews)
You can take time to visit Boston Children's Museum during your travels to Boston. Amble around this vibrant area's waterfront or attend a sporting event.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$56
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
$23
per adult
92% of travellers recommend
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- Boston Vacations
- Visit Boston
- Boston Museum of Fine Arts
- Columbus Park
- Our Lady of Czestochowa Roman Catholic Church
- Museum of Science
- New England Aquarium
- Boston Convention and Exhibition Center
- Boston Tea Party Ship
- Visit Seaport District
- Seaport District Vacations
- Bromfield Art Gallery
- Innovation District
- Boston Common
- Boston Design Center
- Flynn Cruiseport Boston
- Harpoon Brewery
- Cathedral of the Holy Cross
- Boston Medical Center
- Quincy Market
- Liberty Wharf
- Faneuil Hall Marketplace
- Leader Bank Pavilion
- Boston Children's Museum
- Institute of Contemporary Art
- Copley Square
- Shirley-Eustis House
- Isabella Stewart Gardner Museum
- Tufts Medical Center
- Blue Man Group
- Long Wharf
- John F. Kennedy Presidential Library and Museum
- Charles Playhouse
- Boston Public Garden
- Chinatown Vacations
- Zakim Bunker Hill Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.