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.
The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $2,028, price is now CA $1,328 per person
CA $1,328
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,165, price is now CA $1,907 per person
CA $1,907
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,219, price is now CA $1,387 per person
CA $1,387
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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.
The Preserve Sporting Club & Resort

The Preserve Sporting Club & Resort

4 out of 5
Price was CA $8,304, price is now CA $5,445 per person
CA $5,445
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Providence (PVD)
Book a stay at this luxury hotel in Richmond. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Meadowbrook Golf Course and Joseph Langworthy Memorial Park are located nearby.
Wayfinder Newport

Wayfinder Newport

4 out of 5
Price was CA $2,872, price is now CA $1,908 per person
CA $1,908
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Providence (PVD)
Stay at this hotel in Newport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Newport Mansions and Bowen's Wharf 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
The price is CA $202 per night
CA $202
CA $277 total
Jul 26 - Jul 27
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 $329 per night
CA $329
CA $367 total
Aug 3 - Aug 4
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.
The Charles Hotel

The Charles Hotel

5 out of 5
One Bennett Street Cambridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $442 per night
CA $442
CA $513 total
Jul 28 - Jul 29
includes taxes & fees
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Spa
Pet-friendly
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 $204 per night
CA $204
CA $228 total
Aug 2 - Aug 3
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.
Breakfast included
Free airport shuttle
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street Newton MA
Free cancellation
Reserve now, pay when you stay
The price is CA $152 per night
CA $152
CA $170 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington

2 out of 5
130 Middlesex Tpke Burlington MA
Free cancellation
Reserve now, pay when you stay
The price is CA $206 per night
CA $206
CA $230 total
Aug 5 - Aug 6
includes taxes & fees
Book a stay at this business-friendly hotel in Burlington. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Burlington Mall and Louisa May Alcott's Orchard House are 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 $1,328. 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.