Middlesex County Holidays from AU$3,482

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to AU$703 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

Your Middlesex County Holiday

Answer the call of adventure with a customised holiday 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 Centre and Tower Hill Botanic Garden. Tewksbury should also be on the itineraries of all Middlesex County travellers. 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 holiday into reality.

The Latest Middlesex County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was AU$4,203, price is now AU$3,482 per person
AU$3,482
per person
27 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,150 reviews)
Great location. Polite and professional staff. Attractive, clean room with comfortable bed.

Reviewed on 6 Oct 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was AU$5,973, price is now AU$4,279 per person
AU$4,279
per person
27 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.

Reviewed on 7 Oct 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was AU$5,556, price is now AU$4,263 per person
AU$4,263
per person
27 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9/10 Wonderful! (246 reviews)
Lean room, nice staff but the elevator broke and it took a while to fix it

Reviewed on 1 Oct 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was AU$5,238, price is now AU$4,114 per person
AU$4,114
per person
27 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
We love the Whitney and it is our first choice when in Boston and we refer many to stay with you. The property is lovely, the location fantastic and staff excellent.

Reviewed on 30 Sept 2025

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Price was AU$6,028, price is now AU$4,737 per person
AU$4,737
per person
27 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.4/10 Exceptional! (377 reviews)
Great Staff, very nice room. Ideal location for exploring Boston history and access to the T

Reviewed on 19 Sept 2025

Middlesex County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Laurence G. Hanscom Field Airport (BED)
Top Sights
Hopkinton State Park, Ashland State Park and Nashua River Rail Trail

Our pick of the best Middlesex County Hotel Deals

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway, Everett, MA
Fully refundableReserve now, pay when you stay
The price is AU$483 per night from 29 Oct to 30 Oct
AU$483
29 Oct - 30 Oct
includes taxes & fees
9.6/10 Exceptional! (3,290 reviews)
"Very nice hotel but did not really recognise VIP status"

Reviewed on 1 Oct 2025

Encore Boston Harbor
The Charles Hotel

The Charles Hotel

4 out of 5
One Bennett Street, Cambridge, MA
The price is AU$511 per night from 31 Oct to 1 Nov
AU$511
31 Oct - 1 Nov
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Excellent location around Harvard Square walkable area. The hotel has beautiful and very comfy rooms and common areas in the lobby are just gorgeous."

Reviewed on 1 Oct 2025

The Charles Hotel
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave, Wakefield, MA
Fully refundableReserve now, pay when you stay
7.4/10 Good! (2,193 reviews)
"Location is safe. Property and room are clean. Negative is that we're on the 2nd floor and there isn't an elevator. Other issue is that we're in a room directly above the lounge and they're playing music loud and performing karaoke until 11 pm. We have to leave super early in the morning so I hope ..."

Reviewed on 30 Sept 2025

Get rates
Lakeside Inn
See all 1,168 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Middlesex County holiday package cost?
Maybe less than you imagined — from as low as AU$3,482, in fact! By bundling hotels, flights and car rentals into your own customized holiday package, your trip to Middlesex County is just a few clicks away.
How do I get a cheap travel package to Middlesex County?
Secure flights that fit your schedule, add a hotel room to your booking and watch how much you save with a Middlesex County holiday package. It's as easy as that! From hotels and flights to activities and rental cars, Expedia is your gateway to cheap travel. And with over 550 airlines and 1 000 000 properties around the globe to select from, you'll never be short of choice.
Where should I stay in Middlesex County?
Cambridge is an excellent city to visit. It draws in many wanderers who come to see its top sights, such as Harvard Square and Harvard University.
What are the top hotels in Middlesex County?
Take a look at Hampton Inn Boston/Natick and Encore Boston Harbour. They're top picks for many travellers to Cambridge. If Somerville is on your itinerary, Four Points by Sheraton Boston Newton and Hilton Boston/Woburn are top-notch options.
How far in advance should I book my Middlesex County holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to take off. This is usually the cheapest time to book. If circumstances have left you booking late, last-minute deals to Middlesex County occasionally appear in the weeks leading up to departure.
What does an Expedia Middlesex County travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your dream Middlesex County getaway. You can also add on a few activities and experiences once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a Middlesex County travel package?
Bundling your bookings into a Middlesex County holiday package is the most convenient way to organise your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Middlesex County Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You get to decide. We have access to more than 550 airline partners worldwide, so you have options galore when creating your Middlesex County adventure.
If I'm not able to travel, can I cancel my Middlesex County holiday package?
It's good to know that you can cancel your Middlesex County booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.