Maidstone Holidays from AU$1,046

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
TRYP by Wyndham Wellington, Tory Street

TRYP by Wyndham Wellington, Tory Street

4 out of 5
Te Aro
per person
3 Nov - 7 Nov
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
9.2/10 Wonderful! (644 reviews)
Very comfortable bed. Had all the facilities..Old hotel but newly renovated in traditional style.Only comment is that could provide Shower cap and makeup (magnifying) mirror. The complimentary options in lobby appreciated.

Reviewed on 3 Aug. 2025

Wharekauhau Luxury Country Estate

Wharekauhau Luxury Country Estate

5 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Sydney (SYD) to Wellington (WLG)
9.8/10 Exceptional! (8 reviews)
Naumi Hotel Wellington

Naumi Hotel Wellington

4.5 out of 5
Te Aro
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Sydney (SYD) to Wellington (WLG)
8.8/10 Excellent! (1,001 reviews)
A lovely hotel. Cant fault anything in the hotel. It was such a lovely place to stay. I will stay again next time I’m in Wellington .

Reviewed on 20 Jul. 2025

Adina CityLife Wellington

Adina CityLife Wellington

4 out of 5
Wellington CBD
per person
3 Nov - 7 Nov
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
8.8/10 Excellent! (1,006 reviews)
Clean and quiet, modern and well equipped

Reviewed on 8 Aug. 2025

Rydges Wellington Airport

Rydges Wellington Airport

4.5 out of 5
Rongotai
per person
3 Nov - 7 Nov
found 1 day ago
Return flight included
Sydney (SYD) to Wellington (WLG)
9/10 Wonderful! (1,005 reviews)
So convenient - literally adjacent to the airport. Walk off the plane to your hotel room

Reviewed on 6 Aug. 2025

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
Default Image

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 Moonshine Park.

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$122 per night from 31 Aug to 1 Sept
AU$122
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (1,527 reviews)
"This place is awesome. Clean. The staff are very friendle, they have Good food and the location is fantastic. I put a 3 star for the area around the property because the carpark is grose, but its a public carpark so not the hotels fault. We had the terrace room. Nice pillows, comfy bed, nice sized ..."

Reviewed on 5 Aug. 2025

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 AU$174 per night from 17 Aug to 18 Aug
AU$174
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Good value for money and helpful, friendly staff"

Reviewed on 8 Aug. 2025

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 AU$128 per night from 17 Aug to 18 Aug
AU$128
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,326 reviews)
"Fantastic central city location. Very quiet. Staff were awesome."

Reviewed on 3 Aug. 2025

Gilmer Apartment Hotel
See all 461 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
Cheap Holidays
Cheap Holidays
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$1,046. 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

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

Catch an event at Trentham Racecourse during your trip to Upper Hutt. You can enjoy the cafes while in the area.

Trentham Racecourse

Activities

South African rugby supporters on tour at Panhead brewery

Private Wellington Craft Beer Full Day Tour

AU$311
per adult
Private Wellington Craft Beer Full Day Tour
Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

AU$183
per adult
Remutaka Rail Trail Mountain Bike Explorer Cycle Tour
Sleepy Seal at the Cape Palliser Seal Colony

Scenic South Wairarapa Full Day Tour from Wellington

AU$987
per adult
Scenic South Wairarapa Full Day 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.