Middlesex County Holidays
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Top Flight + Hotel Deals in Middlesex County
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
€3,337
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great hotel at a terrific site. The North End restaurants and Faneuil Hall are both at walkable distances. Everywhere we were in the Hotel there was always a staff member asking if we needed help. We loved out stay at the Boston Harbor Hotel.
Reviewed on 22 Sept 2026
Raffles Boston
Back Bay
€2,809
per person
27 Oct - 3 Nov
found 22 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
The room is beautiful, minimalist, luxurious, and extremely comfortable. In my opinion, it’s perfect for a solo traveler or, especially, for a couple. Since the room is on the smaller side, I personally wouldn’t consider it ideal for families traveling with children.
For a romantic getaway, however, it was absolutely perfect. One of the highlights is having an incredible and highly sought-after restaurant right inside the building. The dining experience was exceptional — the food was impeccable, the atmosphere was beautiful, and it truly added another level to our stay. I highly recommend making the restaurant part of the experience.
To make our stay even more special, I hired a local company, Our Love Box (@ourlovebox on Instagram), to create a romantic surprise in the room. I ordered a gorgeous bouquet of 100 roses along with a full romantic room setup, and the result was absolutely stunning.
What impressed me even more was how seamless everything was. They handled the entire setup and came back the following day to remove all of the decorations. Once they were finished, you couldn’t even tell there had been a setup in the room — everything was left exactly as it was before.
Overall, the entire experience was incredible. Between the luxurious and comfortable room, the exceptional dining experience, and the romantic setup, it was truly memorable. I highly recommend this experience for couples celebrating an anniversary, birthday, proposal, or simply looking for a special
Reviewed on 21 Sept 2026
Top hotels in Middlesex County
Encore Boston Harbor
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
€314
18 Oct - 19 Oct
includes taxes & fees
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
€274
4 Oct - 5 Oct
includes taxes & fees
Lakeside Inn
595 North Ave Wakefield MA
Fully refundableReserve now, pay when you stay
€114
27 Sept - 28 Sept
includes taxes & fees
8.2/10 Very good! (889 reviews)
"Chambre spacieuse, vue sur lac et propre. Restaurant en pleine boite de nuit on ne s'entendait pas, honteux et petit dejeuner a revoir. Le jour du depart petit dejeuner dans la boite de nuit, vacanciers d'un tourbus qui stagnaient sur leur table en attendant le depart, sans manger, j'ai du manger ..."
Reviewed on 23 Sept 2026
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 €798, 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.
Stay near popular Middlesex County attractions
Harvard Square
9.0/10 (3,936 reviews)
With a visit to Harvard Square, a favourite shopping spot in Cambridge, you can browse for souvenirs. Experience the fascinating museums and acclaimed art galleries in this vibrant area.
Massachusetts Institute of Technology
9.2/10 (1,465 reviews)
Immerse yourself in an atmosphere of academia at the architecturally rich, museum-filled campus of one of America’s most celebrated universities.
Kendall Square
9.2/10 (492 reviews)
You can learn about the history of Cambridge with a trip to Kendall Square. Experience the acclaimed art galleries or attend a sporting event in this vibrant area.
Photo by Ana Lei
Assembly Row
9.2/10 (414 reviews)
You can search for that perfect souvenir at Assembly Row during your visit to Somerville.
Burlington Mall
8.6/10 (564 reviews)
You can search for that perfect souvenir at Burlington Mall during your trip to Burlington. Amble around this vibrant area's riverfront or attend a sporting event.
Brandeis University
8.4/10 (194 reviews)
Enjoy the student vibe when you visit Brandeis University during your trip to Waltham. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
New England Sports Center
8.8/10 (204 reviews)
Catch an event at New England Sports Center during your trip to Marlborough. You can attend a sporting event while in the area.
Lowell Memorial Auditorium
7.6/10 (40 reviews)
Enjoy a performance at Lowell Memorial Auditorium, a popular theatre in Lowell. You can attend a sporting event while in the area.
What to do in Middlesex County
Boston Old Town Trolley Hop-on Hop-Off City Tour
€42
per adult
90% of travellers recommend
Boston: Scenic Harbor Cruise (Dog-Friendly)
€27
per adult
100% of travellers recommend
City Cruises Boston: Sunset Cruise
€41
per adult
82% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
