Roslindale Vacations from ￥241,120

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Roslindale Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was ￥316,609, price is now ￥241,120 per person
￥241,120
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,086 reviews)
Elegant hotel in a great area of the city. The staff was welcoming and attentive. The beds were comfortable ensuring a great night sleep.

Reviewed on Nov 11, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥378,501, price is now ￥262,690 per person
￥262,690
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Staff went above and beyond!

Reviewed on Nov 9, 2025

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥362,329, price is now ￥256,244 per person
￥256,244
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,323 reviews)
Great part of town, close to everything. Great stay!

Reviewed on Nov 13, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥421,324, price is now ￥310,096 per person
￥310,096
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
Rooms were spotless, service was outstanding

Reviewed on Nov 13, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥384,475, price is now ￥288,264 per person
￥288,264
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
This hotel has it all, best in class care and service.

Reviewed on Oct 24, 2025

Where to stay in Roslindale

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

Roslindale Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥28,621 per night from Nov 16 to Nov 17
￥28,621
￥34,104 total
Nov 16 - Nov 17
includes taxes & fees
9.6/10 Exceptional! (3,620 reviews)
Hotel was gorgeous and the service was excellent

Reviewed on Nov 7, 2025

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥12,887 per night from Nov 23 to Nov 24
￥12,887
￥15,008 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (2,234 reviews)
The bathrooms were always well attended to and my room was spotless when I showed! Front desk was also very kind and responsive

Reviewed on Nov 11, 2025

The Revolution Hotel
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥20,731 per night from Nov 30 to Dec 1
￥20,731
￥24,142 total
Nov 30 - Dec 1
includes taxes & fees
9.2/10 Wonderful! (4,026 reviews)
Love it, will stay again!!

Reviewed on Nov 12, 2025

citizenM Boston North Station
See all 3,778 properties in Roslindale
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 Roslindale vacation package cost?
Customize your Roslindale vacation package from a low ￥241,120. Choose from any combination of rental cars, flights and hotels to put together the trip you've been dreaming of. Be sure to add on some activities and experiences!
How do I get a cheap travel package to Roslindale?
Combine your flights and hotels, add extras such as activities or a rental car, and save with a Roslindale vacation package. You won't just score awesome discounts on your trip — you'll have plenty of choice too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 properties around the globe. Your next big adventure starts right here, right now!
Where should I stay in Roslindale?
A visit to Roslindale isn't complete until you've seen Fenway Park and TD Garden. Stay within walking distance for easy access to these popular sights.
What are the top hotels in Roslindale?
Modern Style Cozy Private Apt is one of Roslindale's most popular hotels. Book a room here and you can rest easy knowing you're in capable hands.
How far in advance should I book my Roslindale vacation?
Your safest bet is to book early. Air carriers usually release flight tickets around a year in advance, and this is an ideal opportunity to score some of the cheapest prices. Just been told you should take all your vacation days in a few weeks? Don't fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Roslindale travel package include?
That depends on what you're looking for. If you're traveling by yourself, you might decide to combine hotels and flights. Taking the whole crew to Roslindale? A travel package including hotels, rental cars and flights might be a better fit. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Roslindale travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you've created your package, you can add on tours and activities. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Roslindale Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from around the world. With so many choices, finding the right carrier to get you to Roslindale will be a cinch.
If I'm not able to travel, can I cancel my Roslindale vacation package?
We totally get it — life doesn't always go according to plan. If you've locked in a Roslindale vacation package and need to cancel or amend it, we can help. We suggest checking out our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,190
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥12,060
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥8,312
per adult
86% of travellers recommend
Boston Harbor Sunset 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.