Maidstone Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 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

    Packages with flights are ATOL protected

Your Maidstone Holiday

Say goodbye to the hassle of planning and hello to a Maidstone holiday package. With the finer details organised before you take off, you can focus on discovering this city, starting with Greektown Historic District, which is good for history, dining and culture. Your trip to Maidstone wouldn't be complete without visiting its top attractions, such as McAuliffe Woods Conservation Area Trail Trailhead. A couple of clicks is all it takes to build a customised Maidstone holiday on Expedia.

Top hotels in Maidstone

Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E Windsor ON
The price is £115 per night from 12 May to 13 May
£115
12 May - 13 May
includes taxes & fees
8.6/10 Excellent! (3,189 reviews)
Had to wait in line for 25 minutes to check in.

Reviewed on 15 Apr 2026

Caesars Windsor - A Caesars Rewards Destination
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East Windsor ON
Fully refundable
The price is £93 per night from 26 Apr to 27 Apr
£93
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (1,359 reviews)
Breakfast choices were very good especially the fact that there was multigrain bread!

Reviewed on 15 Apr 2026

Holiday Inn Express Windsor Waterfront by IHG
Holiday Inn & Suites Windsor Ambassador Bridge by IHG

Holiday Inn & Suites Windsor Ambassador Bridge by IHG

3.5 out of 5
1855 Huron Church Road Windsor ON
Fully refundable
The price is £73 per night from 26 Apr to 27 Apr
£73
26 Apr - 27 Apr
includes taxes & fees
7.4/10 Good! (1,000 reviews)
Originally when we went to check-in and was told our room was ready, we went and it was still unclean so we went downstairs and dealt with a very apologetic kind, patient front desk person who offered us an upgrade, which was fantastic. The parking was amazing. It was free very well lit And the room ...

Reviewed on 12 Apr 2026

Holiday Inn & Suites Windsor Ambassador Bridge by IHG
See all 428 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
Beach Holidays
Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Maidstone travel package cost?
We make it simple to see the world, with Maidstone travel packages starting from as low as . You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add some experiences and tours to your travel itinerary?
If I'm not able to travel, can I cancel my Maidstone travel package?
It's hard to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Maidstone travel package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Maidstone?
Just think of all the thrilling things you could do in Maidstone with a pile of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and extras into a Maidstone travel package. You have loads of choice when you book with Expedia too. In fact, you can take your pick of more than 550 airlines and 1,000,000 hotels around the globe. Whether you're taking a holiday with the entire family or travelling on your own, planning a trip to Maidstone is better with a package.
Does Expedia offer Book Now, Pay Later Maidstone holidays?
Good news! We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply pick the payment plan best suited to your needs during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budgets, so you can book that well-deserved holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you want to grab an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your getaway.

How far in advance should I book my Maidstone holiday?
Reserving your tickets early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, discount flights to Maidstone sometimes become available a few weeks before departure.
What does an Expedia Maidstone travel package include?
From hotels and flights to car rentals, Expedia can help you craft a Maidstone package that fits you. Heading away for a week or longer? Give some thought to a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, a hotel and airfare deal may be more your style. Activities can also be added once you've made your booking. Our travel packages make it easy to save and plan.
What should I know before booking a Maidstone travel package?
Discover deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we've got them all. You'll save a tidy sum just by combining your bookings. Whether you're embarking on a ski adventure or relaxing on a sunny beach, your dream getaway is only a few clicks away.
Can I choose my airline with a Maidstone Expedia travel package?
The choice is all yours! We offer more than 550 airlines across the globe, so you can design your Maidstone holiday according to your budget and style.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.