Bayside Vacation Packages 2026 from $676

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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.

Inn on Boltwood

$676

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Boston (BOS)

9.4/10 Exceptional! (875 reviews)

We had an a very nice stay. Lovely accommodations The staff is top notch. They were always polite, professional and helpful. The grounds are well manicured and lovely. The inn is conveniently located and within walking distance to downtown. We would return.

Reviewed on Oct 10, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$1,051

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

This hotel is one of, if not the, nicest hotels I have ever stayed at around the world. The level of service is second to none, and hotel itself, physically, is incredibly elegant. Being situated on Boston Harbor puts this hotel over the top and into a class of its own.

Reviewed on Oct 16, 2026

Battery Wharf Hotel, Boston Waterfront

North End

$882

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Boston (BOS)

9/10 Wonderful! (2,041 reviews)

Raffles Boston

Back Bay

Save 100% on your flight

$1,129

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Boston (BOS)

9.6/10 Exceptional! (332 reviews)

A stunning hotel with super helpful staff. Would highly recommend the Raffles, from start to finish it was excellent and we’ll definitely be back.

Reviewed on Oct 14, 2026

Boston Lodge and Suites

Dorchester

$852

per person

Dec 4 - Dec 7

found 21 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

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

450 Summer Street Boston MA

$302 nightly

$352 total

Oct 31 - Nov 1

Total with taxes and fees

9.2/10 Wonderful! (4,903 reviews)

"Great location, clean rooms great staff"

Reviewed on Oct 17, 2026

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

$175 nightly

$204 total

Nov 8 - Nov 9

Total with taxes and fees

Seaport Hotel Boston

1 Seaport Lane Boston MA

$219 nightly

$254 total

Nov 1 - Nov 2

Total with taxes and fees

9.6/10 Exceptional! (5,116 reviews)

"The room was clean & nice and the staff was super nice. There was not a hot tub and we did not eat breakfast there"

Reviewed on Oct 17, 2026

See all 4,009 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.