Middlesex County Vacation Packages

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Your Middlesex County Vacation

Answer the call of adventure with a customized vacation package to Middlesex County. Wherever your travels take you and whatever your plans are, get ready to discover a destination that'll make you truly feel alive. A trip to Middlesex County wouldn't be complete without experiencing some of its most renowned cities, starting with Marlborough. Two of the most popular attractions here include Apex Entertainment Centre and Tower Hill Botanic Garden. Tewksbury should also be on the itineraries of all Middlesex County travellers. Visitors to this destination love Burlington Mall and Veterans Memorial Park. When it's time to stop dreaming and start discovering, Expedia will help turn your Middlesex County vacation into reality.

Top vacation destinations in Middlesex County

An aerial view of a town with a central square, a church, and surrounding residential areas.

Marlborough

Marlborough
A snowy town with a train station, a highway, and residential buildings.

Acton

Acton

Top Middlesex County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Raffles Boston

Raffles Boston

Back Bay
Save 100% on your flight
CA $1,215
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (329 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
CA $1,601
per person
Dec 13 - Dec 17
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great location. A bit pricey for the size room. Easy to get most places by walking .

Reviewed on Oct 4, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
Save 100% on your flight
CA $1,584
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (485 reviews)
Beautiful hotel Wonderful rooms and kids absolutely loved the vault ! Looking forward to staying again :)

Reviewed on Oct 3, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
Save 100% on your flight
CA $1,376
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (458 reviews)
The Langham, Boston

The Langham, Boston

Downtown Boston
Save 100% on your flight
CA $1,606
per person
Dec 13 - Dec 17
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The staff were incredibly helpful & nice. The hotel was beautiful & great location

Reviewed on Oct 4, 2026

Middlesex County Hotel Deals

Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
CA $408
CA $456 total
Oct 28 - Oct 29
includes taxes & fees
9.6/10 Exceptional! (4,228 reviews)
"Great place convenient to everything in Boston!!!"

Reviewed on Oct 4, 2026

Encore Boston Harbor
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
CA $216
CA $293 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (2,679 reviews)
"The AC did not work well - it was hot , and other rooms were not available to change ."

Reviewed on Oct 5, 2026

Hyatt Regency Boston/Cambridge
Lakeside Inn

Lakeside Inn

595 North Ave Wakefield MA
Fully refundableReserve now, pay when you stay
CA $185
CA $206 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very good! (954 reviews)
"The view is nice and the rooms are okay. It’s nice to have free breakfast, but it was not particularly good. An average hotel would do better. My room came with a clean scent but with some sort of cleaning residue all over my nightstand. This place more or less falls into the “not the worst if you ..."

Reviewed on Oct 4, 2026

Lakeside Inn
See all 1,216 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 CA $1,215, 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 historic town square with brick buildings, a red bus, and a Harvard sign.

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 fascinating museums and acclaimed art scene in this vibrant area.
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A large building with a dome and columns, surrounded by well-maintained hedges and trees.

Massachusetts Institute of Technology

9.2/10 (1,465 reviews)
Immerse yourself in an atmosphere of academia at the architecturally rich, museum-filled campus of one of America’s most celebrated universities.
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A cityscape with a river, modern buildings, and a bridge.

Kendall Square

9.2/10 (492 reviews)
You can learn about the history of Cambridge when you stop by Kendall Square. Experience the acclaimed art scene or attend a sporting event in this vibrant area.
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A planter with white and purple flowers, a yellow giraffe statue, and a building with a red awning.
Photo by Ana Lei

Assembly Row

9.2/10 (414 reviews)
You can find the perfect gifts to bring home at Assembly Row during your visit to Somerville.
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Burlington Mall

8.6/10 (564 reviews)
You can do some window-shopping at Burlington Mall during your visit to Burlington. Amble around this vibrant area's riverfront or attend a sporting event.
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Lowell Memorial Auditorium

7.6/10 (40 reviews)
Enjoy a show at Lowell Memorial Auditorium, a storied theater in Lowell. You can attend a sporting event while in the area.
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New England Sports Center

8.8/10 (204 reviews)
Catch an event at New England Sports Center during your trip to Marlborough. You can attend a sporting event while in the area.
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Brandeis University

8.4/10 (194 reviews)
Explore the campus of Brandeis University, during your trip to Waltham. Stroll along the riverfront or experience the 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

CA $69
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $117
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

CA $51
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
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.