Middlesex County Holidays

  • Plan, book, travel with confidence

    • Better together

    Save up to S$134 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

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 S$412 per night from 29 Oct to 30 Oct
S$412
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 S$436 per night from 30 Oct to 31 Oct
S$436
30 Oct - 31 Oct
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.

Frequently asked questions

How much does a Middlesex County holiday package cost?
Maybe less than you imagined — from as low as , 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.