Middlesex County Vacations & Trips from ￥276,260

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

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The Latest Middlesex County 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 ￥379,865, price is now ￥276,260 per person
￥276,260
per person
Jan 25 - Jan 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
The room appeared clean but in trying to plug in charging cables I discovered a Qtip under the bedside table. Other than that, the staff was helpful, room service rapid and helpful and all courteous.

Reviewed on Dec 22, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥836,153, price is now ￥441,898 per person
￥441,898
per person
Jan 25 - Jan 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Everything was wonderful including a delicious breakfast. We will definitely return.

Reviewed on Dec 17, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was ￥560,765, price is now ￥360,681 per person
￥360,681
per person
Jan 25 - Jan 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Thank you for the room upgrade. I really appreciated it.

Reviewed on Dec 20, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥651,182, price is now ￥421,017 per person
￥421,017
per person
Jan 25 - Jan 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
It was ok noting like the one overseas.

Reviewed on Dec 7, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was ￥494,966, price is now ￥321,530 per person
￥321,530
per person
Jan 25 - Jan 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

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 ￥36,361 per night from Jan 6 to Jan 7
￥36,361
￥40,615 total
Jan 6 - Jan 7, 2026
includes taxes & fees
9.6/10 Exceptional! (3,456 reviews)
Egg and sausge sandwich at dunkun donuts.

Reviewed on Dec 17, 2025

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 ￥51,853 per night from Jan 10 to Jan 11
￥51,853
￥60,124 total
Jan 10 - Jan 11, 2026
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
Thank you for the room upgrade. I really appreciated it.

Reviewed on Dec 20, 2025

The Charles Hotel
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Fully refundableReserve now, pay when you stay
The price is ￥12,003 per night from Jan 4 to Jan 5
￥12,003
￥13,407 total
Jan 4 - Jan 5, 2026
includes taxes & fees
7.4/10 Good! (3,043 reviews)
Nice

Reviewed on Dec 18, 2025

La Quinta Inn & Suites by Wyndham Boston Somerville
See all 1,273 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 ￥276,260, 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.