Windermere Vacation Packages

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Top Holiday Package Deals in Windermere

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Greenwood by IHG

Holiday Inn Express Hotel & Suites Greenwood by IHG

2.5 out of 5
Price was CA $1,574, price is now CA $1,226 per person
CA $1,226
per person
Jun 17 - Jun 21
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9/10 Wonderful! (1,012 reviews)
Great place off the expressway. Staff were great!

Reviewed on Apr 10, 2026

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
Price was CA $1,937, price is now CA $1,546 per person
CA $1,546
per person
Jun 17 - Jun 21
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.8/10 Exceptional! (1,855 reviews)
Rize is a great restaurant! The only additional requests I would ask is that a small personal fridge be an option, or an option to clean the mini bar since it’s not weighted. As well as an option to include a microwave in the room. Though not all stays are extended beyond a day or two, families still love to stay here and may be staying for a few days. This would support those extended stays, just as options to be added into the room, or in the mini bars case, the fridge to be cleared.

Reviewed on Apr 10, 2026

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was CA $1,741, price is now CA $1,420 per person
CA $1,420
per person
Jun 17 - Jun 21
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.4/10 Exceptional! (899 reviews)
I really enjoyed my stay at the Omni. The hotel is aesthetically pleasing (great for pictures) and very clean. The staff was wonderful and friendly. The food I had at 8 Notch, which is a breakfast/ lunch style restaurant downstairs, was good. I will definitely stay here in the future.

Reviewed on Apr 1, 2026

The village

The village

4 out of 5
Near Westside
Price was CA $2,631, price is now CA $2,195 per person
CA $2,195
per person
May 23 - May 25
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Indianapolis (IND)
8/10 Very Good! (46 reviews)
Would definitely stay again!

Reviewed on Mar 6, 2026

Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was CA $2,185, price is now CA $1,826 per person
CA $1,826
per person
Jun 17 - Jun 21
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.8/10 Exceptional! (1,849 reviews)
This is a great hotel with fabulous staff!

Reviewed on Apr 10, 2026

Where to stay in Windermere

Find the best Windermere areas and neighborhoods for the activities you enjoy most. Learn more about Windermere
Downtown Indianapolis

Downtown Indianapolis

4 out of top 10 points of interest in this area
4.5/5(57 area reviews)

As the city's cultural, political, and economic hub, this neighborhood boasts historic districts, performing arts venues, and museums. Enjoy nightlife on Meridian Street and Massachusetts Avenue, or stroll along the Indianapolis Canal Walk.

Find hotels in Downtown Indianapolis

Windermere Hotel Deals

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
2721 E 86th Street Indianapolis IN
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 10 to May 11
CA $247
CA $290 total
May 10 - May 11
includes taxes & fees
9.8/10 Exceptional! (1,862 reviews)
Rize is a great restaurant! The only additional requests I would ask is that a small personal fridge be an option, or an option to clean the mini bar since it’s not weighted. As well as an option to include a microwave in the room. Though not all stays are extended beyond a day or two, families still ...

Reviewed on Apr 10, 2026

Ironworks Hotel Indy
Sonesta Select Indianapolis Carmel

Sonesta Select Indianapolis Carmel

3 out of 5
37 W 103rd Street Indianapolis IN
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Apr 19 to Apr 20
CA $129
CA $148 total
Apr 19 - Apr 20
includes taxes & fees
7.8/10 Good! (1,156 reviews)
It was very clean and comfortable room.

Reviewed on Apr 10, 2026

Sonesta Select Indianapolis Carmel
Omni Severin Hotel

Omni Severin Hotel

4 out of 5
40 West Jackson Place Indianapolis IN
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Apr 19 to Apr 20
CA $231
CA $274 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (918 reviews)
Room was fine, but a little run down. Water stain on the lower part of our drapes and a few broken or damaged pieces of furniture in the room. The biggest let down however was the closed pool due to rebalancing of chemicals with no notice. We only live a couple hours away so the pool was part of ...

Reviewed on Apr 6, 2026

Omni Severin Hotel
See all 2,477 properties in Windermere
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Frequently asked questions

How much does a Windermere vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Windermere from just CA $1,226. And the more you bundle, the more cash you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Windermere?
Just imagine all the fabulous things you could do in Windermere with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your hotel and flights into a Windermere vacation package. You have loads of choice with Expedia too. In fact, you can take your pick of over 550 airlines and 1,000,000 properties across the globe. Whether you're taking a break with the whole family or traveling on your own, organizing a trip to Windermere is better with a package.
Where should I stay in Windermere?
With loads to discover in Windermere, it'd be handy for you to stay near its attractions. Topgolf, Nickel Plate District Amphitheater and Fishers Banquet Center are some interesting ones to add to your itinerary.
How far in advance should I book my Windermere vacation?
To bag cheap prices, book as early as you can. Air carriers generally release tickets, along with some of the lowest fares, around a year prior to departure. Hotels, car rental and activities should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway in Windermere, there are always lots of great deals to be had on Expedia. Check them out now!
What does an Expedia Windermere travel package include?
Expedia has all you need to arrange your Windermere getaway, but what goes into your package is your choice. Select from a combination of flights, hotels and rental cars. After some activities or tours to fill in your time? Once you've made your booking, you can add them on too. No matter your budget, there's a vacation package to meet your needs.
What should I know before booking a Windermere travel package?
Bundling your bookings into a Windermere vacation package is the easiest way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Windermere Expedia vacation package?
Yes, you sure can. We offer more than 550 partner airlines around the world, so opt for the carrier that fits your budget needs.
If I'm not able to travel, can I cancel my Windermere vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you've booked your Windermere vacation package in the last 24 hours, you may be able to cancel or change it for no charge. Your hotel, airline or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Windermere

Indianapolis Motor Speedway

Indianapolis Motor Speedway

4.5/5(26 reviews)

Buckle up at the world’s most famous speedway and experience G-force thrills usually reserved for race car drivers.

Indianapolis Motor Speedway
Children's Museum of Indianapolis

Children's Museum of Indianapolis

3.5/5(7 reviews)

Dinosaurs and pirate ships, interactive exhibits, games and toys from a bygone age — it’s all at this children’s wonderland.

Children's Museum of Indianapolis
Indiana Convention Center

Indiana Convention Center

4/5(24 reviews)

Learn about the events happening at Indiana Convention Center during your trip to Indianapolis. Experience the area's acclaimed theater scene and fascinating museums.

Indiana Convention Center

Things to do

Indianapolis: Crossroads Ghosts Haunted Walking Tour

Wicked Wraiths of White River: Indianapolis Ghost Tour

CA $33
per adult
Wicked Wraiths of White River: Indianapolis Ghost Tour
Step into the shadows and discover the haunting tales of our city's past.

Wicked Wraiths of White River: Indianapolis Ghost Tour

CA $44
per adult
Wicked Wraiths of White River: Indianapolis Ghost Tour
See all activities in Indianapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.