Middlesex County Holidays

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Top destinations in Middlesex County

An aerial view of a beach surrounded by autumn-colored trees.
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Westford

Westford
A town with a prominent white church steeple, a snow-covered landscape, and a mix of residential and commercial buildings.
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Chelmsford

Chelmsford

Our pick of the best Middlesex County Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is NZ$364 per night from 1 July to 2 July
NZ$364
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (2,401 reviews)
"Good access and comfortable interior, including the nice coffee bar"

Reviewed on 28 June 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 NZ$458 per night from 19 July to 20 July
NZ$458
19 July - 20 July
includes taxes & fees
9.6/10 Exceptional! (3,885 reviews)
"Perfect hotel! I had a great time and room was luxurious!"

Reviewed on 29 June 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 NZ$613 per night from 7 July to 8 July
NZ$613
7 July - 8 July
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Perfection every way"

Reviewed on 29 June 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 holiday package cost?
Maybe less than you imagined — from as low as , in fact! By bundling hotels, flights and car rentals into your own customized holiday 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 holiday 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 Harbour. They're top picks for many travellers 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 holiday?
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 holiday package is the most convenient way to organise 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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday 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

9.0/5 (3,936 reviews)
With a visit to Harvard Square, a favourite shopping spot in Cambridge, you can browse for souvenirs. Experience the acclaimed art galleries and fascinating museums in this vibrant area.
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What to do in Middlesex County

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

NZ$89
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

NZ$58
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

NZ$135
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.