Dorchester Vacations

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    Save up to ￥109,000 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Front of property
    Aug 24 - Aug 28

    Eurostars The Boxer + Flight

    West End
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,507 reviews)
    "Amazing staff!"
    Reviewed June 2, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - HND • 1 stop
    ￥419,613
    ￥356,251
    per traveler
    found 1 day ago
    Eurostars The Boxer
  • Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar
    Aug 24 - Aug 28

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - HND • 1 stop
    ￥657,291
    ￥456,585
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Breakfast, lunch and brunch served
    Aug 24 - Aug 28

    The Langham, Boston + Flight

    Downtown Boston
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    "The rooms were clean, and friendly staff"
    Reviewed May 31, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - HND • 1 stop
    ￥545,104
    ￥431,372
    per traveler
    found 1 day ago
    The Langham, Boston
  • Game room
    Aug 6 - Aug 10

    Meco Hotel - Hostel + Flight

    West End
    4 nights
    2.0 star property
    8.6/10 - Excellent (436 reviews)
    "Desk clerk did not mention the birth I had contained a powered couch which I found out later was the easiet way to get into the under bed storage bin"
    Reviewed June 1, 2026
    Roundtrip • Osaka (KIX) - Boston (BOS)
    KIX - BOS • 2 stops BOS - KIX • 2 stops
    ￥485,348
    ￥397,804
    per traveler
    found 1 hour ago
    Meco Hotel - Hostel
  • Deluxe Single Room, 1 King Bed | Bathroom | Shower, hair dryer, towels, soap
    Aug 6 - Aug 10

    The Inn at Fireside Tavern Sherborn + Flight

    Sherborn
    4 nights
    2.0 star property
    10/10 - Exceptional (2 reviews)
    "Very cool place to stay outside of the city. Beautiful property with well maintained grounds. Short drive to the Natick mall which has so many places to shop and eat. Would recommend! 5/5⭐️"
    Reviewed May 26, 2026
    Roundtrip • Osaka (KIX) - Boston (BOS)
    KIX - BOS • 1 stop BOS - KIX • 1 stop
    ￥969,386
    ￥823,601
    per traveler
    found 2 hours ago
    The Inn at Fireside Tavern Sherborn

Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
Downtown 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.

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 ￥22,558 per night from Jun 4 to Jun 5
￥22,558
￥26,268 total
Jun 4 - Jun 5
includes taxes & fees
6.8/10 (1,750 reviews)
"Location wise not too close to most of the places, where we wanted to go. Property was clean. Staff was not very accommodating however, not bad even."

Reviewed on Jun 2, 2026

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 ￥29,284 per night from Jun 7 to Jun 8
￥29,284
￥34,100 total
Jun 7 - Jun 8
includes taxes & fees
8.4/10 Very Good! (1,483 reviews)
"Lovely room. Helpful staff. The bar and food on offer were limited. We had just one evening meal - a lasagna and had to send it back to be reheated as it wasn’t hot in the middle. Snacks , pizza, BLT sandwiches were good. The situation close to the super path along the bay was brilliant for people ..."

Reviewed on Jun 3, 2026

DoubleTree by Hilton Hotel Boston Bayside
Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston

2 out of 5
60 Ridgewood St Boston MA
The price is ￥11,996 per night from Jun 8 to Jun 9
￥11,996
￥17,465 total
Jun 8 - Jun 9
includes taxes & fees
8.2/10 Very Good! (51 reviews)
"I got as far as driving into the neighborhood and decided it did not feel safe and would not be comfortable parking my vehicle. I drove the 2.5 hours home rather than stay there"

Reviewed on May 28, 2026

Homestay In Fields Corner Area Boston
See all 4,303 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 , 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

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,335
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

￥7,086
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥13,180
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
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.