Middlesex County Vacations & Trips from ￥406,160

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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 Middlesex County 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 ￥559,352, price is now ￥406,160 per person
￥406,160
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Front desk clerk Gonzalo provided excellent customer service. We love staying at this hotel!

Reviewed on Mar 27, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥953,365, price is now ￥637,704 per person
￥637,704
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was ￥813,103, price is now ￥601,841 per person
￥601,841
per person
Jun 20 - Jun 24
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Room was spacious, clean & well set up. Nice that they use Dyptique hand soap shampoo & shower gel. That is a 5 star touch. Bed was nice and very quiet location.

Reviewed on Mar 22, 2026

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was ￥607,393, price is now ￥468,738 per person
￥468,738
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,431 reviews)
Beautiful spacious room, and every staff member was so kind. Customer service was above and beyond. Wouod definitely book again!

Reviewed on Mar 27, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥766,702, price is now ￥594,530 per person
￥594,530
per person
Jun 20 - Jun 24
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

Middlesex County Hotel Deals

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
The price is ￥38,213 per night from Apr 5 to Apr 6
￥38,213
￥42,684 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (3,603 reviews)
I will definitely be going back I had a great time staff very friendly and the entire resort was very clean. I give this resort a 10.!

Reviewed on Mar 23, 2026

Encore Boston Harbor
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is ￥22,865 per night from Mar 30 to Mar 31
￥22,865
￥30,214 total
Mar 30 - Mar 31
includes taxes & fees
9/10 Wonderful! (2,283 reviews)
Rooms were clean. The staff was great. The food and staff at the restaurant was spot on.

Reviewed on Mar 26, 2026

Hyatt Regency Boston/Cambridge
Courtyard by Marriott Boston-Cambridge

Courtyard by Marriott Boston-Cambridge

3.5 out of 5
777 Memorial Dr Cambridge MA
Fully refundableReserve now, pay when you stay
The price is ￥18,538 per night from Mar 29 to Mar 30
￥18,538
￥27,417 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Great place to stay nearby MIT buildings

Reviewed on Mar 26, 2026

Courtyard by Marriott Boston-Cambridge
See all 1,295 properties in Middlesex County
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 Middlesex County vacation package cost?
Maybe less than you imagined — from as low as ￥406,160, in fact! By bundling hotels, flights and car rentals into your own customized vacation package, your trip to Middlesex County is just a few clicks away.
How do I get a cheap travel package to Middlesex County?
Secure flights that fit your schedule, add a hotel room to your booking and watch how much you save with a Middlesex County vacation package. It's as easy as that! From hotels and flights to activities and rental cars, Expedia is your gateway to cheap travel. And with over 550 airlines and 1,000,000 properties around the globe to select from, you'll never be short of choice.
Where should I stay in Middlesex County?
Cambridge is an excellent city to visit. It draws in many wanderers who come to see its top sights, such as Harvard Square and Harvard University.
What are the top hotels in Middlesex County?
Take a look at Hampton Inn Boston/Natick and Encore Boston Harbor. They're top picks for many travelers to Cambridge. If Somerville is on your itinerary, Four Points by Sheraton Boston Newton and Hilton Boston/Woburn are top-notch options.
How far in advance should I book my Middlesex County vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to take off. This is usually the cheapest time to book. If circumstances have left you booking late, last-minute deals to Middlesex County occasionally appear in the weeks leading up to departure.
What does an Expedia Middlesex County travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your dream Middlesex County getaway. You can also add on a few activities and experiences once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a Middlesex County travel package?
Bundling your bookings into a Middlesex County vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Middlesex County Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to decide. We have access to more than 550 airline partners worldwide, so you have options galore when creating your Middlesex County adventure.
If I'm not able to travel, can I cancel my Middlesex County vacation package?
It's good to know that you can cancel your Middlesex County booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.