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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was €1,176, price is now €1,014 per person
€1,014
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (1,323 reviews)
Nice room, staff was nice at the front desk.

Reviewed on 7 Nov 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was €1,609, price is now €1,230 per person
€1,230
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
So what a hotel. A small issue was handled with disproportionate kindness! The ambiance is lively, the space is luxe, the team from bellhop to GM were all exceptional. Thank you all for my short stop with you

Reviewed on 5 Nov 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was €1,661, price is now €1,307 per person
€1,307
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
This hotel has it all, best in class care and service.

Reviewed on 24 Oct 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was €1,241, price is now €1,059 per person
€1,059
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,175 reviews)
Really appreciated the diffuser

Reviewed on 3 Nov 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,219, price is now €1,046 per person
€1,046
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (2,221 reviews)
clean and fabulous staff

Reviewed on 7 Nov 2025

Top hotels in Middlesex County

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway, Everett, MA
Fully refundableReserve now, pay when you stay
The price is €270 per night from 1 Dec to 2 Dec
€270
1 Dec - 2 Dec
includes taxes & fees
9.6/10 Exceptional! (3,368 reviews)
Beautiful, excellent service and accommodations, highly recommend!

Reviewed on 4 Nov 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 €285 per night from 7 Dec to 8 Dec
€285
7 Dec - 8 Dec
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
Comfortable beds!

Reviewed on 3 Nov 2025

The Charles Hotel
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
Fully refundableReserve now, pay when you stay
The price is €81 per night from 7 Dec to 8 Dec
€81
7 Dec - 8 Dec
includes taxes & fees
7.4/10 Good! (3,021 reviews)
Easy check in. Clean room

Reviewed on 1 Nov 2025

La Quinta Inn & Suites by Wyndham Boston Somerville
See all 1,226 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 €1,014, 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.