Maidstone Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Where to stay in Maidstone

Find the best Maidstone areas and neighborhoods for the activities you enjoy most. Learn more about Maidstone
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Trentham

5 out of top 10 points of interest in this area

Trentham is noteworthy for its restaurants, and you can make a stop at top attractions like Trentham Racecourse and Upper Hutt College Field.

Find hotels in Trentham

Maidstone Hotel Deals

James Cook Hotel Grand Chancellor

James Cook Hotel Grand Chancellor

4.5 out of 5
147 The Terrace Wellington
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Jul 19 to Jul 20
CA $93
CA $108 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (1,780 reviews)
"I’d definitely stay there again"

Reviewed on Jul 10, 2026

James Cook Hotel Grand Chancellor
Rydges Wellington

Rydges Wellington

4.5 out of 5
75 Featherston St Wellington
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Jul 19 to Jul 20
CA $125
CA $144 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"Great central place to stay"

Reviewed on Jul 8, 2026

Rydges Wellington
Gilmer Apartment Hotel

Gilmer Apartment Hotel

3.5 out of 5
10 Gilmer Terrace Wellington
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Jul 24 to Jul 25
CA $90
CA $104 total
Jul 24 - Jul 25
includes taxes & fees
8.8/10 Excellent! (1,562 reviews)
"Quiet, clean apartment. Easy check in and friendly helpful staff."

Reviewed on Jul 10, 2026

Gilmer Apartment Hotel
See all 533 properties in Maidstone
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.
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Frequently asked questions

How much does a Maidstone vacation package cost?
Chart your own course with our Maidstone vacation packages, which start from only . Choose the hotels and flights that suit your travel plans. Then, add on some activities or tours for a one-of-a-kind getaway.
How do I get a cheap travel package to Maidstone?
Book everything in one place with our Maidstone vacation packages. We have incredible bargains on flights, hotels and more that'll keep your travel budget happy and your adventurousness alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to select from, you have countless opportunities to mix and match as you please.
Where should I stay in Maidstone?
Maidstone is home to numerous interesting places to see, such as Trentham Racecourse. Secure a room in a hotel nearby and make sightseeing hassle-free.
How far in advance should I book my Maidstone vacation?
It all depends on the air carrier, but it's usually possible to compare international fares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky travelers will sometimes score a cheaper seat just weeks prior to departure dates.
What does an Expedia Maidstone travel package include?
With Expedia, you can select any combination of flights, hotels and car rentals to build your perfect Maidstone travel package. Once you've made your booking, you can add on the fun things like tours and experiences. Remember, the more you bundle, the greater the savings!
What should I know before booking a Maidstone travel package?
Booking all the parts of your trip together is a terrific way to save. Combine your car rentals, airfares and hotels into a tidy little package. But hotels aren't your only option. Expedia features all kinds of properties, including vacation rentals like beachside villas and short-term homes. You've got loads of choices!
Can I choose my airline with a Maidstone Expedia vacation package?
You can, and with over 550 airlines to pick from throughout the world, you're spoiled for choice. Scroll through the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Maidstone vacation package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Booked your Maidstone vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For further information, browse our Customer Service Portal. We're here to help you each step of the way.

Stay near popular Maidstone attractions

Brewtown Upper Hutt

You can take time to visit Brewtown Upper Hutt during your travels to Upper Hutt.
See properties

Things to do

Te Awa Kairangi Grade 2 Scenic Rafting Tour

Te Awa Kairangi Grade 2 Scenic Rafting Tour

CA $120
per adult
Te Awa Kairangi Grade 2 Scenic Rafting Tour
Lunch and wine tastings at Le Gra Vineyard.

Private Wairarapa Wine Delights Tour from Wellington

CA $832
per adult
Private Wairarapa Wine Delights Tour from Wellington
Inspecting a live beehive at Greytown Honey

Private Martinborough Foodie Delights Tour from Wellington

CA $848
per adult
Private Martinborough Foodie Delights Tour from Wellington
See all activities in Upper Hutt
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.