Bayside Vacations from $421
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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.
The Westin Boston Seaport District
Seaport District
Save 100% on your flight
Price was $662, price is now $421 per person
$421
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (2,387 reviews)
We enjoyed our stay here very much, but the check-in process needs to be improved. The line to check in was so long, about a 15-20 minute wait! The difficulty in all this was that we had done a pre-check a couple of hours earlier, and all we needed to do was pick up the room key, but we still had to wait in that terribly long line.
Reviewed on Jul 12, 2026
Good Hotels Boston
South End
Save 100% on your flight
Price was $1,364, price is now $726 per person
$726
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
The Atlas Hotel
Allston
Save 100% on your flight
Price was $1,159, price is now $710 per person
$710
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
We loved the Atlas Hotel, located directly opposite Harvard on a quiet street in Boston.
It is a beautifully appointed hotel with good-sized rooms (we took a corner room and were very happy with it), and it is well-suited to international travellers (space for bags, etc). The bed is comfortable, and the rooms are well serviced and clean throughout our stay, with lovely linens, towels, etc. We did have a good hairdryer, essential for me (long hair) and a steamer. We did ask for an iron and ironing board. The iron was super, but the ironing board had seen better days! This was mentioned and replaced quickly.
What makes this hotel are the staff; they are friendly, always say hello, and ask if they can help, which made it a pleasure to be here and stay here. This was in the middle of the World Cup, so I can imagine they were busy with many travellers arriving and leaving. We liked the tasty breakfasts and the great cocktails on the top floor of the hotel, which has a good view over the Boston environs. I would be delighted to stay here again in the future. A special place where you feel special for being here.
Reviewed on Jul 10, 2026
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $2,310, price is now $1,469 per person
$1,469
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.
Reviewed on Jul 6, 2026
Where to stay in Bayside
Find the best Bayside areas and neighborhoods for the activities you enjoy most. Learn more about Bayside
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.
Bayside Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
$219 nightly
The price is $254 total per night from Jul 26 to Jul 27
$254 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (4,569 reviews)
"What an amazing location! We went to Boston for a concert at the Leader Bank Pavillion which is 1 block away. Also on the same weekend the Tall Ships were there and because the hotel is on the harbor the views were incredible! The rooms were lovely and the pool was fun as was the bar!"
Reviewed on Jul 12, 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
$156 nightly
The price is $181 total per night from Aug 9 to Aug 10
$181 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (2,442 reviews)
"Very clean and the complimentary shuttle was convenient."
Reviewed on Jul 11, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $185 total per night from Aug 2 to Aug 3
$185 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (2,736 reviews)
"Our room had the four bunk beds and it was awesome! Safe, excellent construction with comfortable beds, perfect for our family of four (our teenagers, of course, loved being on the top bunks). I wasn’t sure how the “bathroom/shower down the hall” was going to be, but it turned out to be great! Having ..."
Reviewed on Jul 11, 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.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$47
per adult
80% of travellers recommend
Boston Summer Nights Tour and River Cruise
$50
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.