Middlesex County Vacations & Trips from $499

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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 Center and Tower Hill Botanic Garden. Tewksbury should also be on the itineraries of all Middlesex County travelers. 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 destinations in Middlesex County

A river with a wooden bridge, surrounded by dense green foliage.

Lowell

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

Chelmsford

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

Marlborough

Marlborough
A residential area with a prominent church, residential houses, and a mix of autumn-colored trees.

Tewksbury

Tewksbury
A waterfall, a stone building, and leafless trees.

Groton

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

Westford

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

Acton

Acton
A street lined with historic brick buildings, a clock tower, and blooming trees.

Hudson

Hudson
A lake surrounded by autumn-colored trees.

Hopkinton

Hopkinton

The Latest Middlesex County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

Dorchester
$499
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Raffles Boston

Raffles Boston

Back Bay
$1,663
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
Staff and room

Reviewed on Sep 4, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$738
per person
Nov 11 - Nov 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
$2,148
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (484 reviews)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
$1,873
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (451 reviews)
Great hotel in great location. Staff earned five star status.

Reviewed on Sep 6, 2026

Find the Best Middlesex County Vacation Packages

Middlesex County Essential Information

Language
English
Currency
U.S dollars
Top Sights
Veterans Memorial Park, Hopkinton State Park and Ashland State Park

Middlesex County Hotel Deals

Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
$328 nightly
$367 total
Oct 4 - Oct 5
Total with taxes and fees
Encore Boston Harbor
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA
$190 nightly
$220 total
Sep 20 - Sep 21
Total with taxes and fees
9/10 Wonderful! (2,628 reviews)
"Convenient for parents who come in from out of town to help with another September 1st move in day."

Reviewed on Sep 6, 2026

Hyatt Regency Boston/Cambridge
Lakeside Inn

Lakeside Inn

595 North Ave Wakefield MA
Fully refundable
$101 nightly
$113 total
Sep 10 - Sep 11
Total with taxes and fees
Lakeside Inn
See all 1,275 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.

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 fascinating museums and acclaimed art scene in this vibrant area.
See properties
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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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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Tsongas Center at UMass Lowell

8.0/10 (99 reviews)
Enjoy a show at Tsongas Center at UMass Lowell, 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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What to do in Middlesex County

Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$37
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
Boston: Scenic Harbor Cruise

Boston: Scenic Harbor Cruise (Dog-Friendly)

$32
per adult
100% of travellers recommend
Boston: Scenic Harbor Cruise (Dog-Friendly)
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities in Middlesex County
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