Maidstone Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Maidstone Vacation

Say goodbye to the hassle of planning and hello to a Maidstone vacation package. With the finer details organized 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 customized Maidstone vacation on Expedia.

Top Holiday Package Deals in Maidstone

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Chatham

Comfort Inn Chatham

2.5 out of 5
Price was CA $583, price is now CA $534 per person
CA $534
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Windsor (YQG)
8.8/10 Excellent! (896 reviews)
Comfortable sleep, shower had wall mounted bulk shampoo, conditioner, and body wash. No need to battle it out with tiny shampoo bottles.

Reviewed on May 2, 2026

Hotel STRY

Hotel STRY

2 out of 5
Price was CA $818, price is now CA $754 per person
CA $754
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Windsor (YQG)
10/10 Exceptional! (29 reviews)
What a great location! Such a fun night away! Loved th day spa pure located right under it! The missing O bar is so cool and delicious!

Reviewed on Feb 13, 2026

Nicklin House

Nicklin House

3 out of 5
Price was CA $795, price is now CA $736 per person
CA $736
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
9.4/10 Exceptional! (97 reviews)
Really enjoyed our stay. Paul (proprietor) was immensely helpful and very interesting to boot. We had an outstanding breakfast both mornings, and fell in love with the old home charm. Would definitely recommend staying here. It was a fun, first time bnb experience for us and will definitely be returning.

Reviewed on May 1, 2026

Days Inn by Wyndham Leamington

Days Inn by Wyndham Leamington

2.5 out of 5
Price was CA $923, price is now CA $893 per person
CA $893
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
7.8/10 Good! (930 reviews)
Clean rooms. Good breakfast only thing could use more fresh cut fruit. Plenty of parking. There is even a deck area with tables and a bbq. Ill try that next time.

Reviewed on Apr 28, 2026

Dream Estate Inn

Dream Estate Inn

3.5 out of 5
Price was CA $917, price is now CA $891 per person
CA $891
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
9.4/10 Exceptional! (127 reviews)
This was a lovely place to stay. The room was spacious, comfortable, ultra clean and had a little gratitude practice available to guests. While the bed and breakfast is self serve, the complementary items were healthy, easy and convenient. This is a lovely place with a lot of thoughtful touches. I highly recommend this hidden gem in Leamington Ontario.

Reviewed on Nov 5, 2025

Maidstone Hotel Deals

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 CA $159 per night from May 5 to May 6
CA $159
CA $215 total
May 5 - May 6
includes taxes & fees
8.6/10 Excellent! (3,215 reviews)
The room was clean with a stunning view. The room was super hot though. Even when the thermostat was turned down the temperature didn't regulate well. We went for a concert and the venue was great. Everything ran smooth.

Reviewed on May 3, 2026

Caesars Windsor - A Caesars Rewards Destination
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from May 10 to May 11
CA $139
CA $166 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,084 reviews)
Bed was comfy and staff was friendly

Reviewed on May 2, 2026

DoubleTree by Hilton Windsor Hotel & Suites
Comfort Inn & Suites Ambassador Bridge

Comfort Inn & Suites Ambassador Bridge

2.5 out of 5
2330 Huron Church Rd Windsor ON
Fully refundable
The price is CA $93 per night from May 10 to May 11
CA $93
CA $111 total
May 10 - May 11
includes taxes & fees
8/10 Very Good! (1,285 reviews)
Room was clean. Staff at front desk was rude when we checked in. Breakfast was not very appetizing. Eggs didnt look like real eggs. Most items were empty when we arrived at 9am. The staff were very friendly when we checked out. Good location.

Reviewed on May 1, 2026

Comfort Inn & Suites Ambassador Bridge
See all 435 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?
Starting from as low as CA $534, you can create your own Maidstone package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Maidstone?
Booking a Maidstone vacation package with Expedia is a smart way to save. We have access to more than 550 partner airlines and 1,000,000 hotel options across the globe. With such an awesome range to pick from, you'll have no issues putting together your dream escape.
How far in advance should I book my Maidstone vacation?
While not all airlines release tickets early, it's usually possible to look up international flights on Expedia up to 12 months in advance. This is the time when you'll nab some fantastic deals. If you're booking last minute, there's a chance you could get lucky. Sometimes the lowest prices emerge a few weeks before departure.
What does an Expedia Maidstone travel package include?
Flights, car rentals and hotels — we bring you the very best bargains. All you have to do is pick your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it simple to create an awesome Maidstone vacation.
What should I know before booking a Maidstone travel package?
You can save big by combining your flights, hotels and rental cars. Once you've created your package, you can add on sightseeing tours or experiences. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Maidstone Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You get to decide. We have access to more than 550 airline partners throughout the world, so you have options galore when planning your Maidstone adventure.
If I'm not able to travel, can I cancel my Maidstone vacation package?
You can cancel your Maidstone booking if your travel plans have changed. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.