Longwood Vacations from ￥77,962

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Longwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥110,023, price is now ￥77,962 per person
￥77,962
per person
Oct 19 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
8.8/10 Excellent! (1,536 reviews)
What a nice surprise! We booked a room the night before an early flight and the hotel was great. We were upgraded to a junior suite and the room was spacious and comfortable. The location is super convenient and I’d definitely stay here again the next time I’m in Boston.

Reviewed on Aug 3, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥262,427, price is now ￥168,902 per person
￥168,902
per person
Oct 19 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
The location is great and amenities are great

Reviewed on Aug 3, 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Price was ￥535,126, price is now ￥393,432 per person
￥393,432
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (5,143 reviews)
The best part was the check in time at 3pm and check out time of 12pm. Perfect walking distance to local restaurants and shopping. Valet service was excellent and even though $65 may be a little pricey, you do not need to move your car for 24 hrs! Staff was very friendly and helpful. Check in and check out was a breeze!

Reviewed on Aug 3, 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was ￥125,603, price is now ￥96,599 per person
￥96,599
per person
Oct 19 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
9.2/10 Wonderful! (2,367 reviews)
Amazing stay !

Reviewed on Aug 3, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was ￥130,662, price is now ￥100,534 per person
￥100,534
per person
Oct 19 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
9.6/10 Exceptional! (4,011 reviews)
The private

Reviewed on Aug 3, 2026

Where to stay in Longwood

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

Find hotels in Downtown Boston

Longwood Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥37,020 per night from Aug 20 to Aug 21
￥37,020
￥49,526 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (4,844 reviews)
"I was disappointed that the concierge at the hotel recommended Provincetown to us without really telling us that it wasn’t the best place to go in Cape Cod… meaning that town is only appropriate for a certain type of person and it was not our vibe at all, which I would think the concierge could’ve ..."

Reviewed on Aug 3, 2026

Omni Boston Hotel at the Seaport
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 ￥22,552 per night from Aug 24 to Aug 25
￥22,552
￥26,262 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (2,795 reviews)
"Shared bathroom space was not ideal."

Reviewed on Aug 3, 2026

The Revolution Hotel
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥30,265 per night from Aug 16 to Aug 17
￥30,265
￥41,659 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very Good! (3,064 reviews)
"I was quite disappointed in our room. Having booked a "superior" double queen, I expected at least some room to move and a bathroom of a good size. The choice was between a standard, deluxe, and superior and the room we were put in was less than standard, for sure. Given the many choices in the Boston ..."

Reviewed on Aug 3, 2026

Hilton Boston Park Plaza
See all 4,137 properties in Longwood
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 Longwood vacation package cost?
Starting from as low as ￥77,962, you can create your own Longwood vacation package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Longwood?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into a Longwood vacation package to save a pile of cash. Score even more discounts when you include extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to customize your vacation your way. We offer more than 550 air carriers and 1,000,000 hotel options across the world, so that everyone has a chance to travel and live out those vacation fantasies.
Where should I stay in Longwood?
Stay close to the action. Many people like to book hotels within easy reach of popular attractions, such as Coolidge Corner Theatre, John Fitzgerald Kennedy National Historic Site and Larz Anderson Auto Museum.
What are the top hotels in Longwood?
Get your vacation off to a fantastic start by locking in a room at Sunny Private Room, Longwood, 10min Walk To Fenway. It's one of most sought-after properties in Longwood. Another option is Walking To Fenway Sunny Perfect Home.
How far in advance should I book my Longwood vacation?
Reserving your flight early with Expedia means one less thing to worry about. Many air carriers advertise prices up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, great deals to Longwood are still known to appear in the weeks leading up to departure.
What does an Expedia Longwood travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your perfect Longwood escape. You can also add on tours and activities once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a Longwood travel package?
You'll enjoy excellent savings when you combine your flights, hotels and rental cars into a travel package. Not just that, booking everything in one place makes trip planning easier. So why waste time or money? Whether you're organizing an upscale romantic escape or a low-cost family road trip, check out our package deals today.
Can I choose my airline with a Longwood Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Longwood vacation package?
It's hard to predict what the future holds, so it's comforting to know that you can change or cancel your Longwood vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Stay near popular Longwood attractions

Brookline Arts Center

Enjoy an outing to Brookline Arts Center during your stay in Brookline.
See properties

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,526
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

￥7,680
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥13,653
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.