Bayside Vacations from $732

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Your Bayside Vacation

Our Bayside vacation packages are an easy and handy way to plan and reserve your next break. Experience the magic of this unique neighborhood without the burden of having to plan everything yourself. Some top nearby attractions to see during your trip to Bayside include Nantasket Beach Reservation, World’s End and Hull Lifesaving Museum. Expedia can help turn your dream Bayside vacation into reality, whatever your travel plans or budget.

The Latest Bayside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

Dorchester
$732
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$1,172
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Great location

Reviewed on Oct 13, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
Save 100% on your flight
$1,424
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in. On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.

Reviewed on Oct 6, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

North End
$846
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9/10 Wonderful! (2,041 reviews)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
Save 100% on your flight
$1,149
per person
Dec 10 - Dec 13
found 14 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
9.4/10 Exceptional! (458 reviews)

Where to stay in Bayside

Find the best Bayside areas and neighborhoods for the activities you enjoy most. Learn more about Bayside
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

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.

A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Bayside Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$298 nightly
$347 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (4,909 reviews)
"Things were fine but"

Reviewed on Oct 15, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
$167 total
Nov 10 - Nov 11
Total with taxes and fees
9/10 Wonderful! (2,970 reviews)
"Second time staying here - was in a double room last time with a friend and that was great - the single room very tight - the sink too small to really use without getting water all over. no chair or luggage rack. Clean and sparse. Liked that they had a small gym downstairs. Nice area & close to Boston ..."

Reviewed on Oct 15, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
$254 total
Oct 30 - Oct 31
Total with taxes and fees
Seaport Hotel Boston
See all 3,976 properties in Bayside
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.

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$46
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$37
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
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.