Hillsborough County Vacations & Trips from ￥171,574

Book a Hotel + Flight or Car together to unlock savings

Photo by Zach Siegenthaler

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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 destinations in Hillsborough County

Manchester showing a city
FlightsFlightsHotelsHotels

Manchester

Manchester

The Latest Hillsborough County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was ￥237,796, price is now ￥171,574 per person
￥171,574
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Festive and comfortable beds

Reviewed on Dec 18, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥518,006, price is now ￥298,152 per person
￥298,152
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Everything was wonderful including a delicious breakfast. We will definitely return.

Reviewed on Dec 17, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥371,173, price is now ￥252,120 per person
￥252,120
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
We love the Charles Hotel. From its helpful and friendly staff, spotless and well appointed rooms, and excellent on-site restaurants. It is the perfect place for a winter getaway.

Reviewed on Dec 14, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥418,090, price is now ￥284,254 per person
￥284,254
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (201 reviews)
It was ok noting like the one overseas.

Reviewed on Dec 7, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥326,948, price is now ￥226,253 per person
￥226,253
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (494 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

Hillsborough County Hotel Deals

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St. Manchester NH
Fully refundableReserve now, pay when you stay
The price is ￥19,887 per night from Dec 21 to Dec 22
￥19,887
￥21,577 total
Dec 21 - Dec 22
includes taxes & fees
9/10 Wonderful! (1,085 reviews)
Nice clean room,comfortable bed,nice lounge

Reviewed on Dec 15, 2025

DoubleTree by Hilton Manchester Downtown
Tru by Hilton Manchester Downtown

Tru by Hilton Manchester Downtown

2.5 out of 5
135 Spring Street Manchester NH
Fully refundableReserve now, pay when you stay
The price is ￥15,302 per night from Dec 28 to Dec 29
￥15,302
￥16,603 total
Dec 28 - Dec 29
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
The room was spotless, and the staff was professional and kind.

Reviewed on Dec 13, 2025

Tru by Hilton Manchester Downtown
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Fully refundableReserve now, pay when you stay
The price is ￥14,282 per night from Dec 21 to Dec 22
￥14,282
￥15,496 total
Dec 21 - Dec 22
includes taxes & fees
8.2/10 Very Good! (1,327 reviews)
Staff was good. Room felt not clean.

Reviewed on Dec 18, 2025

Best Western Plus Executive Court Inn & Conference Center
See all 1,214 properties in Hillsborough 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 Hillsborough County vacation package cost?
Our Hillsborough County vacation packages, which start at just ￥171,574, are the easiest way to save precious money. Pick and choose your favorite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Hillsborough County?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Choose the combination that suits you and see your savings stack up. Of course, a travel package is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 properties worldwide, which lets you customize your Hillsborough County vacation.
Where should I stay in Hillsborough County?
You can't beat Manchester. Big-name sights, such as Southern New Hampshire University Arena and New Hampshire International Speedway, will keep you entertained in this vibrant city.
What are the top hotels in Hillsborough County?
Best Western Plus Executive Court Inn & Conference Center and DoubleTree by Hilton Manchester Downtown know how to make their guests feel at home in Manchester. If your itinerary also includes Nashua, check out Country Inn & Suites by Radisson, Manchester Airport, NH and Even Hotels Manchester Airport, an IHG Hotel. Both are very popular with travelers.
How far in advance should I book my Hillsborough County vacation?
It's hard to pick the perfect time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you're unable to do so, don't stress. Budget prices occasionally appear within a few weeks of departure dates.
What does an Expedia Hillsborough County travel package include?
It comes down to what you want. If you're traveling solo, you might decide to bundle hotels and flights. Taking the entire family to Hillsborough County? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a Hillsborough County travel package?
A package can be easier on the wallet than separately booking all you need for your getaway. For example, combine your hotels, flights and rental cars and score big savings. No matter your vacation goals, you're bound to find a package within your budget.
Can I choose my airline with a Hillsborough County Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply pick the airline you want and put together your ideal Hillsborough County getaway.
If I'm not able to travel, can I cancel my Hillsborough County vacation package?
We totally get it — sometimes life doesn't go according to plan. If you've locked in a Hillsborough County vacation package and have to cancel or change it, we're here to help. It's always worth checking out our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or change your itinerary for free. If it's more than 24 hours, your hotel, airline or car rental company may charge a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.