Windermere Vacation Packages
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Top Holiday Package Deals in Windermere
Price found within the past 48 hours. Click for updated prices.
SpringHill Suites by Marriott Indianapolis Downtown
Downtown Indianapolis
CA $1,391
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Indianapolis (IND)
9.2/10 Wonderful! (1,006 reviews)
Great hospitality from the front desk, and very clean. Check in/check out was a smooth process! Breakfast was great!
Reviewed on Oct 25, 2026
Landing Furnished Apartments Near Northside
Near Northside
CA $1,598
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Indianapolis (IND)
8.8/10 Excellent! (8 reviews)
First of all there are no employees at the property. There is NO immediate help. I stayed for four days. I had to call a toll free number and wait for an operator to ask for more toilet paper on day 2 and then never got it before I left. The tv was busted in one of the bedrooms. They text me a code to get into the room, not the building. So after a 15-20 minute phone call I was able to get into the building. The property has approx 50+ 2BR 2BA apts on each floor. There are only 2 elevators right in the middle of the property with 25 apts or more on each side to the left or right. In other words, if you like walking a football field to your room, you’ll love this place. The rooms and bathrooms were very nice (xcept 4 the one TV). Every drawer was labeled with its contents in every room just in case you don’t know where something goes. Oh yea, forget about extra towels - there is a washer and dryer in the apts so you have to clean your own. Don’t forget the detergent because it’s not provided. One more fyi, since your entire stay revolves around the app and no one’s on site to help, if you lose your phone, you’ll never get back in your room again on your own. I hope I’ve been a big help in your decision to stay away from this dreadful place.
Reviewed on Aug 16, 2026
Courtyard by Marriott Indianapolis Downtown
Downtown Indianapolis
CA $1,397
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Indianapolis (IND)
9.2/10 Wonderful! (1,328 reviews)
Everything was as expected. Clean, friendly, safe. Located close to Convention Center & Luca Oil Stadium.
Reviewed on Oct 26, 2026
JW Marriott Indianapolis
Downtown Indianapolis
CA $1,612
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Indianapolis (IND)
9.4/10 Exceptional! (1,375 reviews)
Very nice hotel, clean and helpful staff. Parking is not included, one complaint about stay.
Reviewed on Oct 26, 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
5 out of top 10 points of interest in this area
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.
Mile Square
The fascinating museums and prominent monuments are top of the list for many visitors to Mile Square. A stop by Gainbridge Fieldhouse or Monument Circle might round out your trip.
Wholesale District
If you're spending some time in Wholesale District, Gainbridge Fieldhouse and Indiana Repertory Theatre are top sights worth seeing.
Babe Denny
If you're looking for some top things to see and do in Babe Denny and surrounding area, you can visit Lucas Oil Stadium and Gainbridge Fieldhouse.
Castleton
Castleton is known for its abundant dining options, and you can plan a trip to Castleton Square and Dave & Buster's while you're in town.
Windermere Hotel Deals
Ironworks Hotel Indy
2721 E 86th Street Indianapolis IN
Fully refundableReserve now, pay when you stay
CA $226
CA $264 total
Nov 8 - Nov 9
includes taxes & fees
9.8/10 Exceptional! (2,150 reviews)
"Great"
Reviewed on Oct 26, 2026
Omni Severin Hotel
40 West Jackson Place Indianapolis IN
Fully refundableReserve now, pay when you stay
CA $213
CA $252 total
Nov 15 - Nov 16
includes taxes & fees
The Fontana Hotel
7304 E 21st St Indianapolis IN
Fully refundableReserve now, pay when you stay
CA $163
CA $191 total
Nov 22 - Nov 23
includes taxes & fees
8.2/10 Very good! (1,047 reviews)
"The room and bathroom were clean. The outside was dingy and well used looking. Huge potholes in the parking lot pavement"
Reviewed on Oct 26, 2026
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 Windermere vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Windermere from just CA $1,391. 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.
Things to do
Wicked Wraiths of White River: Indianapolis Ghost Tour
CA $45
per adult
Children's Museum of Indianapolis In-App Audio Tour
CA $14
per traveller
100% of travellers recommend
Wicked Wraiths of White River: Indianapolis Ghost Tour
CA $37
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.