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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,366, price is now CA $810 per person
CA $810
per person
Oct 21 - Oct 23
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,804, price is now CA $1,246 per person
CA $1,246
per person
Nov 11 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 Faneuil Hall Marketplace are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $2,439, price is now CA $1,694 per person
CA $1,694
per person
Oct 6 - Oct 11
just found
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nobadeer Beach and Madequecham Pond are located nearby.
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,843, price is now CA $1,290 per person
CA $1,290
per person
Oct 6 - Oct 11
just found
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this hotel in Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mayflower Beach and Ocean Edge Golf Club are located nearby.
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Price was CA $6,432, price is now CA $4,693 per person
CA $4,693
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Ocean Edge Golf Club and Linnell Landing Beach are located nearby.

Top Middlesex County hotels deals

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 $394 per night
CA $394
CA $440 total
Sep 20 - Sep 21
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.
Spa
Parking included
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 $185 per night
CA $185
CA $255 total
Sep 7 - Sep 8
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.
Pet-friendly
Free WiFi
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 $124 per night
CA $124
CA $138 total
Sep 6 - Sep 7
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 Public Health Museum and Eastern Canal Park are located nearby.
Pool
Pet-friendly
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 $122 per night
CA $122
CA $136 total
Aug 27 - Aug 28
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.
Pool
Breakfast included
The Royal Sonesta Boston

The Royal Sonesta Boston

4 out of 5
40 Edwin H. Land Boulevard Cambridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $219 per night
CA $219
CA $295 total
Sep 6 - Sep 7
includes taxes & fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Pool
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 $198 per night
CA $198
CA $221 total
Aug 30 - Aug 31
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
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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 theater scene and fascinating museums in this vibrant area.
See properties

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 $810. 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.