Middlesex County Vacations & Trips from ￥230,802

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The Latest Middlesex County Vacation Packages

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

The Ellery

3.5 out of 5
Price was ￥253,338, price is now ￥230,802 per person
￥230,802
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,003 reviews)
Everything was excellent. Check in staff could be friendlier.

Reviewed on Jun 30, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥812,996, price is now ￥539,094 per person
￥539,094
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥295,166, price is now ￥272,872 per person
￥272,872
per person
Aug 21 - Aug 23
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,525 reviews)

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was ￥308,177, price is now ￥287,142 per person
￥287,142
per person
Aug 21 - Aug 23
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (2,375 reviews)
Wonderful hotel. The rooftop pool area is beautiful. Very comfortable room. And the staff is so friendly!

Reviewed on Jun 30, 2026

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was ￥298,935, price is now ￥278,594 per person
￥278,594
per person
Aug 21 - Aug 23
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,287 reviews)
Nice and clean. The location was fantastic!

Reviewed on Jun 28, 2026

Middlesex County Hotel Deals

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 ￥27,186 per night from Jul 2 to Jul 3
￥27,186
￥36,381 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (2,396 reviews)
"The staff was hilarious! Multiple staff members made me genuinely laugh. They were helpful and friendly. I also liked the location a lot."

Reviewed on Jul 1, 2026

Hyatt Regency Boston/Cambridge
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
The price is ￥37,928 per night from Jul 27 to Jul 28
￥37,928
￥42,364 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (3,893 reviews)
"Best place to stay while in Boston!"

Reviewed on Jul 1, 2026

Encore Boston Harbor
The Charles Hotel

The Charles Hotel

4 out of 5
One Bennett Street Cambridge MA
Fully refundableReserve now, pay when you stay
The price is ￥52,522 per night from Jul 30 to Jul 31
￥52,522
￥60,898 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"Perfection every way"

Reviewed on Jun 29, 2026

The Charles Hotel
See all 1,276 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 ￥230,802, 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.

Stay near popular Middlesex County attractions

A nighttime street scene with a historic building, street lamps, and a church spire.

Harvard Square

9.0/10 (3,936 reviews)
With a visit to Harvard Square, a favorite shopping spot in Cambridge, you can search for that perfect souvenir. Experience the acclaimed art scene and fascinating museums in this vibrant area.
See properties

What to do in Middlesex County

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,438
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

￥7,223
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Boston: Scenic Harbor Cruise

Boston: Scenic Harbor Cruise (Dog-Friendly)

￥5,005
per adult
100% of travellers recommend
Boston: Scenic Harbor Cruise (Dog-Friendly)
See all activities in Middlesex County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.