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 Coach House

The Coach House

3 out of 5
Price was CA $1,553, price is now CA $1,189 per person
CA $1,189
per person
Dec 26 - Dec 31
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Salem Witch Museum and Salem Pioneer Village 1630 are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $2,831, price is now CA $1,754 per person
CA $1,754
per person
Nov 20 - Nov 24
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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 Faneuil Hall Marketplace and Boston Harbor are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,662, price is now CA $1,943 per person
CA $1,943
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,935, price is now CA $2,187 per person
CA $2,187
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was CA $2,722, price is now CA $2,059 per person
CA $2,059
per person
Nov 20 - Nov 23
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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.

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 $407 per night
CA $407
CA $454 total
Oct 28 - Oct 29
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
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 $184 per night
CA $184
CA $206 total
Nov 1 - Nov 2
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
The price is CA $306 per night
CA $306
CA $397 total
Oct 25 - Oct 26
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 $242 per night
CA $242
CA $270 total
Nov 1 - Nov 2
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
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is CA $215 per night
CA $215
CA $292 total
Nov 1 - Nov 2
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
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street Newton MA
The price is CA $162 per night
CA $162
CA $181 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Pool
Pet-friendly
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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 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.
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 $1,189. 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.