Book Exclusive Middlesex County Vacation Packages

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Search vacation packages deals in Middlesex County's top destinations

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

Marlborough

Vacations
Marlborough

Middlesex County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Pier 7 Condominiums

Pier 7 Condominiums

2 out of 5
Bass River
Price was CA $1,258, price is now CA $909 per person
CA $909
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Stay at this hotel in South Yarmouth. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Cape Cod Inflatable Park and West Dennis Beach are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,777, price is now CA $1,942 per person
CA $1,942
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $2,054, price is now CA $1,468 per person
CA $1,468
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, laundry facilities, and bathrobes. Popular attractions Copley Square and Fenway Park are located nearby.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,870, price is now CA $1,338 per person
CA $1,338
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions West Dennis Beach and Cape Cod Inflatable Park are located nearby.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Price was CA $1,303, price is now CA $937 per person
CA $937
per person
Oct 1 - Oct 4
found 8 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this golf hotel in Danvers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Water Park of New England and Putnam House are located nearby.

Top Middlesex County hotels deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $215 per night
CA $215
CA $292 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Free cancellation
Reserve now, pay when you stay
The price is CA $348 per night
CA $348
CA $389 total
Aug 12 - Aug 13
includes taxes & fees
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
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
Free cancellation
Reserve now, pay when you stay
The price is CA $191 per night
CA $191
CA $213 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this business-friendly hotel in Somerville. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Bedford Plaza Hotel - Boston

Bedford Plaza Hotel - Boston

3 out of 5
340 Great Road Bedford MA
Free cancellation
Reserve now, pay when you stay
The price is CA $126 per night
CA $126
CA $141 total
Aug 2 - Aug 3
includes taxes & fees
Stay at this hotel in Bedford. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Burlington Mall and Minute Man National Historical Park are located nearby.
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive Tewksbury MA
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
CA $152 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eastern Canal Park and Merrimack Repertory Theater are located nearby.
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave Wakefield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $124 per night
CA $124
CA $138 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction MarketStreet Lynnfield is located nearby.
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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 acclaimed art scene and fascinating museums in this vibrant area.
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Photos of local treasures

Browse Middlesex County vacation photos for more inspiration

A gazebo in a park with a sign reading "Stoneham Town Common".
A statue of a man on a pedestal with a date inscription, surrounded by trees and a pathway.
A field of numerous horse-drawn carriages in a rural setting with a backdrop of trees and a distant white building.
A modern architectural building with unique geometric shapes and a curved glass facade.
A collection of various beetles pinned on display.

Frequently asked questions

How much are vacation packages to Middlesex County?
You can land a fantastic hotel and flight bundle for as low as CA $909. With a Travelocity vacation package, a trip to Middlesex County has never looked so good! Save both time and cash and get an early start with packing your suitcases.
Where can I get the best vacation package deals for Middlesex County?
No matter your travel style, Travelocity can help you score the best Middlesex County package deal. The only thing you need to do is mix and match from our 400 airlines and 1,000,000 worldwide properties.
Why should I purchase my Middlesex County vacation bundle with Travelocity?
We've got destinations to suit every kind of globetrotter, first-rate service and support available 24/7. And to top it off, we'll match any cheaper price you discover with our Price Match Guarantee.
Can I save on my Middlesex County car rental if I bundle it with hotels and flights?
You can with our Middlesex County vacation packages. With one of these, there are lots of ways to stretch your vacation budget further. Combine any two or more car, hotel, flight and tour bookings and watch the savings start to add up. With your own ride, all the landmarks in and around Middlesex County are a memorable road trip away.
Which airport is best for Middlesex County?
Logan Intl. Airport (BOS) is where many travelers choose to touch down. Depending on your Middlesex County itinerary, T.F. Green Airport (PVD) and Manchester-Boston Regional Airport (MHT) are also worth considering.
What is there to do in Middlesex County?
You'll be happy to know Middlesex County is brimming with incredible photo-ops, however Apex Entertainment Center and Hopkinton State Park are right up there with the very best.