Maidstone Holidays from AU$904

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Your Maidstone Holiday

Maidstone is calling! Whatever type of adventure you're organising, you can immerse yourself in the best of this neighbourhood with a Maidstone holiday package. There are so many great nearby attractions to add to your schedule during your trip to Maidstone. What you can't miss? Trentham Racecourse and Maidstone Park. Don't just think about it — take action! Reserve your perfect Maidstone holiday with Expedia and experience travel your way.

Top Holiday Package Deals in Maidstone

Price found within the past 48 hours. Click for updated prices.
Naumi Studio Wellington

Naumi Studio Wellington

4 out of 5
Te Aro
Price was AU$1,058, price is now AU$904 per person
AU$904
per person
18 Feb - 21 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
8.6/10 Excellent! (913 reviews)
It was noisy at night

Reviewed on 13 Dec 2025

U Suites on Jessie

U Suites on Jessie

4 out of 5
Te Aro
Price was AU$1,371, price is now AU$1,144 per person
AU$1,144
per person
18 Feb - 21 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
No reviews
The Cobbler Hotel

The Cobbler Hotel

3 out of 5
Te Aro
Price was AU$1,436, price is now AU$1,219 per person
AU$1,219
per person
18 Feb - 21 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
9.6/10 Exceptional! (84 reviews)
Lovely room, gorgeous bed and linen but I think the cleaners are dropping the ball.

Reviewed on 2 Jan 2026

Adina CityLife Wellington

Adina CityLife Wellington

4 out of 5
Wellington CBD
Price was AU$1,167, price is now AU$1,003 per person
AU$1,003
per person
18 Feb - 21 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
8.8/10 Excellent! (1,032 reviews)
An amazing amount of space in the two-bedroom unit. Super location for the shops and waterfront. Would stay there again

Reviewed on 12 Jan 2026

Boulcott Suites

Boulcott Suites

4 out of 5
Te Aro
Price was AU$1,214, price is now AU$1,050 per person
AU$1,050
per person
18 Feb - 21 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
9.2/10 Wonderful! (2,255 reviews)
Awesome place to stay

Reviewed on 12 Jan 2026

Our guide on 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

4 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 Whakatiki Buffer Reserve.

Find hotels in Trentham

Our pick of the best 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 AU$135 per night from 31 Jan to 1 Feb
AU$135
31 Jan - 1 Feb
includes taxes & fees
8.6/10 Excellent! (1,660 reviews)
Convenient central location, helpful staff

Reviewed on 11 Jan 2026

James Cook Hotel Grand Chancellor
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 AU$125 per night from 25 Jan to 26 Jan
AU$125
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (1,426 reviews)
Position of hotel to Wellington attractions was the biggest plus

Reviewed on 7 Jan 2026

Gilmer Apartment Hotel
Rydges Wellington

Rydges Wellington

4.5 out of 5
75 Featherston St Wellington
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 17 Jan to 18 Jan
AU$171
17 Jan - 18 Jan
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
The staff went out of their way to look after us and get a room ready quickly at short notice. This was especially appreciated as we were travelling with 2 young children. The rooms were clean and tidy, beds were comfortable and the extra amenities like the pool were a hit with the kids.

Reviewed on 11 Jan 2026

Rydges Wellington
See all 499 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Maidstone holiday package cost?
Chart your own course with our Maidstone holiday packages, which start from only AU$904. 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 holiday 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 holiday?
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 travellers 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 holiday homes like beachside villas and short-term homes. You've got loads of choices!
Can I choose my airline with a Maidstone Expedia holiday 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 holiday package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Booked your Maidstone holiday 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.

Discover the most popular places to visit in Maidstone

Maidstone Park

3.5/5(6 reviews)

Explore the great outdoors at Maidstone Park, a lovely green space in Upper Hutt. You can enjoy the cafes while in the area.

Maidstone Park

Trentham Racecourse

3.5/5(5 reviews)

You can take time to visit Trentham Racecourse during your travels to Upper Hutt. You can enjoy the cafes while in the area.

Trentham Racecourse

Activities

Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

AU$174
per adult
Remutaka Rail Trail Mountain Bike Explorer Cycle Tour
Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

AU$174
per adult
100% of travellers recommend
Remutaka Rail Trail Mountain Bike Explorer Cycle Tour
Lunch and wine tastings at Le Gra Vineyard.

Private Wairarapa Wine Delights Tour from Wellington

AU$900
per adult
Private Wairarapa Wine 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.