Maidstone Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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

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

Top hotels in Maidstone

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 €67 per night from 1 Feb to 2 Feb
€67
1 Feb - 2 Feb
includes taxes & fees
8.6/10 Excellent! (1,659 reviews)
Room was clean

Reviewed on 5 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 €83 per night from 19 Jan to 20 Jan
€83
19 Jan - 20 Jan
includes taxes & fees
8.8/10 Excellent! (1,421 reviews)
Amenities was a delightful surprise (laundry wash/dry facilities)

Reviewed on 2 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 €96 per night from 16 Jan to 17 Jan
€96
16 Jan - 17 Jan
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
Gave an early check in on a cold rainy day

Reviewed on 5 Jan 2026

Rydges Wellington
See all 502 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.

Frequently asked questions

How much does a Maidstone holiday package cost?
Chart your own course with our Maidstone holiday 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 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 rentals 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.

Things to do

Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

Remutaka Rail Trail Mountain Bike Explorer Cycle Tour

€98
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

€98
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

€510
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.