Middlesex County Holidays

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Top destinations in Middlesex County

FlightsFlightsHotelsHotels

Westford

Westford

Top Flight + Hotel Deals in Middlesex County

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (566 reviews)
Nice 2-bedroom, 2-bathroom apt. Perfect for family stay. Safe building. Beds weren’t the most comfortable.

Reviewed on 31 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Our favorite hotel in Boston with amazing gym, pool, spa and food. We come here monthly and have tried other hotels but they just can’t compete.

Reviewed on 31 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
18 Sept - 22 Sept
found 9 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
My second time here n we love it!!!

Reviewed on 31 Jul 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (413 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul 2025

Top hotels in Middlesex County

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
Fully refundableReserve now, pay when you stay
The price is €167 per night from 17 Aug to 18 Aug
€167
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,031 reviews)
"Overall, great stay! The entire staff was friendly and helpful throughout our stay."

Reviewed on 29 Jul 2025

Hyatt Regency Boston/Cambridge
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway, Everett, MA
Fully refundableReserve now, pay when you stay
The price is €301 per night from 25 Aug to 26 Aug
€301
25 Aug - 26 Aug
includes taxes & fees
9.6/10 Exceptional! (3,130 reviews)
"My second time here n we love it!!!"

Reviewed on 31 Jul 2025

Encore Boston Harbor
The Charles Hotel

The Charles Hotel

4 out of 5
One Bennett Street, Cambridge, MA
Fully refundableReserve now, pay when you stay
The price is €350 per night from 30 Aug to 31 Aug
€350
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"The staff is professional, polite, helpful and attentive. The parking is extremely convenient and easy and the facility and restaurants were always excellent."

Reviewed on 31 Jul 2025

The Charles Hotel
See all 1,164 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.

Frequently asked questions

How much does a Middlesex County holiday package cost?
Maybe less than you imagined — from as low as €953, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.