Dorchester Vacations from ￥226,502

Book a Hotel + Flight or Car together to unlock savings

The Latest Dorchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was ￥284,550, price is now ￥226,502 per person
￥226,502
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,150 reviews)
Our experience at Hotel AKA Back Bay was above & beyond hospitality & location for any Boston traveler!

Reviewed on Oct 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥436,057, price is now ￥286,484 per person
￥286,484
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!

Reviewed on Sep 15, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥382,848, price is now ￥277,483 per person
￥277,483
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Everything I always expected it would be. Total class hotel and we were treated as valued guests include an upgrade. We will return.

Reviewed on Oct 3, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥320,182, price is now ￥239,048 per person
￥239,048
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
Excellent location around Harvard Square walkable area. The hotel has beautiful and very comfy rooms and common areas in the lobby are just gorgeous.

Reviewed on Oct 1, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥347,465, price is now ￥261,394 per person
￥261,394
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
We love the Whitney and it is our first choice when in Boston and we refer many to stay with you. The property is lovely, the location fantastic and staff excellent.

Reviewed on Sep 30, 2025

Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
Downtown Boston which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(2,415 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.

Find hotels in Downtown Boston

Dorchester Hotel Deals

Ramada by Wyndham Boston

Ramada by Wyndham Boston

2.5 out of 5
800 Morrissey Blvd, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥16,485 per night from Oct 26 to Oct 27
￥16,485
￥19,197 total
Oct 26 - Oct 27
includes taxes & fees
6.6/10 (1,443 reviews)
"Wifi needs work. Keeps disconnecting in room"

Reviewed on Oct 2, 2025

Ramada by Wyndham Boston
DoubleTree by Hilton Hotel Boston Bayside

DoubleTree by Hilton Hotel Boston Bayside

4 out of 5
240 Mount Vernon Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥26,545 per night from Oct 5 to Oct 6
￥26,545
￥30,912 total
Oct 5 - Oct 6
includes taxes & fees
8.4/10 Very Good! (1,391 reviews)
"No nearby restaurant, but the hotel offered a market grill."

Reviewed on Oct 1, 2025

DoubleTree by Hilton Hotel Boston Bayside
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥35,275 per night from Oct 30 to Oct 31
￥35,275
￥47,089 total
Oct 30 - Oct 31
includes taxes & fees
9/10 Wonderful! (4,082 reviews)
"For our trip to Boston, this location worked out well! The hotel was comfortable, well appointed and had ample onsite parking. We were able to park the car and leave it for the 4 days-walked or took “the T” everywhere. Lots of restaurants nearby but the hotel also had really good options too!"

Reviewed on Sep 28, 2025

Omni Boston Hotel at the Seaport
See all 3,874 properties in Dorchester
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 Dorchester vacation package cost?
Maybe less than you might think — from only ￥226,502, actually! By combining flights, hotels and car rentals into your own custom-built travel package, your Dorchester escape is just clicks away.
How do I get a cheap travel package to Dorchester?
Our Dorchester vacation packages promise plenty of savings for the savvy explorer. For the best deals, simply bundle your flights, hotels and extras (including tours) into an affordable package. But great bargains are only the start of your next amazing adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels globally to choose from. No matter your style or budget, there's a package that's perfect for you.
Where should I stay in Dorchester?
Vacationers come from all over the world to see Fenway Park and TD Garden in Dorchester. Stay within a stone's throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Dorchester?
Lg Suite For Up To 6 Ppl/1 Floor and Home2 Suites by Hilton Boston South Bay are among the most well-known hotels in Dorchester. Why not take a look at the facilities and rates at each and then make up your mind?
How far in advance should I book my Dorchester vacation?
While not all air carriers advertise ticket prices early, you can normally look up international fares on Expedia up to 12 months in advance. This is the time when you'll bag some incredible deals. If you're booking late, you may still be in luck. Sometimes the cheapest prices become available a few weeks before departure.
What does an Expedia Dorchester travel package include?
You can select from any combination of rental cars, hotels and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to creating your ideal Dorchester escape.
What should I know before booking a Dorchester travel package?
Locking in all the parts of your vacation together is an excellent way to save. Bundle your car rentals, airfares and hotels into a convenient package. But it's not just hotels. Expedia features all sorts of properties, including vacation rentals such as beachfront villas and serviced residences. You've got choices galore!
Can I choose my airline with a Dorchester Expedia vacation package?
You can, and with over 550 airlines to select from throughout the world, you have loads of choice. Search the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Dorchester vacation package?
Your situation can change unexpectedly, so yes. You may be able to cancel or amend your Dorchester vacation package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Need more information? Check out our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Things to do

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

￥1,463
per traveler
84% of travellers recommend
Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,572
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

￥4,980
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.