Middlesex County Holidays from NZ$3,222

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Top destinations in Middlesex County

FlightsFlightsHotelsHotels

Westford

Westford

The Latest Middlesex County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
29 Oct - 1 Nov
found 18 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul. 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
29 Oct - 1 Nov
found 18 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug. 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
29 Oct - 1 Nov
found 18 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on 5 Aug. 2025

The Hotel Salem

The Hotel Salem

3 out of 5
per person
29 Oct - 1 Nov
found 18 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.2/10 Wonderful! (1,013 reviews)
Check in was friendly and quick, staff.was helpful with transportation options and suggestions for activities, dining and shopping. The hotel is literally next to shopping, dining and short walking distance to popular attractions.

Reviewed on 7 Aug. 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
29 Oct - 1 Nov
found 18 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (433 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

Our pick of the best Middlesex County Hotel Deals

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 NZ$308 per night from 1 Sept to 2 Sept
NZ$308
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (2,084 reviews)
"Lovely spacious room and friendly staff and love Boston 😃"

Reviewed on 8 Aug. 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 NZ$629 per night from 1 Sept to 2 Sept
NZ$629
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,165 reviews)
"This property was definitely a 5 star location. My ooh's and ahh's started we drive uo to the property. The lobby with the flower art was magnificent and aromatic! The curving escalator was remarkable. The chandeliers are gorgeous. Our room with the view of the harbor was breathtaking. Our bathroom ..."

Reviewed on 8 Aug. 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 NZ$715 per night from 24 Aug to 25 Aug
NZ$715
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Smells fantastic in this place. Perfect linens and room arrangement. It is a cut above the surrounding hotels."

Reviewed on 7 Aug. 2025

The Charles Hotel
See all 1,169 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 NZ$3,222, 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.