Windermere Vacation Packages

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

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Top Holiday Package Deals in Windermere

Price found within the past 48 hours. Click for updated prices.
Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was CA $1,610, price is now CA $1,339 per person
CA $1,339
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Indianapolis (IND)
9.2/10 Wonderful! (391 reviews)
Front desk very helpful. Convenient location. Very nice stay.

Reviewed on Jun 2, 2026

The Alexander, Autograph Collection

The Alexander, Autograph Collection

4 out of 5
Downtown Indianapolis
Price was CA $1,721, price is now CA $1,400 per person
CA $1,400
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Indianapolis (IND)
8.8/10 Excellent! (1,004 reviews)
Right in the perfect location to quickly go eat or shop. Room was immaculate. Beautifully decorated. Even had a hand held steamer for your wrinkled clothes. We will 100% stay at this wonderful hotel again!

Reviewed on May 29, 2026

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was CA $1,657, price is now CA $1,366 per person
CA $1,366
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Indianapolis (IND)
9.4/10 Exceptional! (1,078 reviews)
Great hotel. Staff was wonderful. Location is excellent; right downtown. Only complaint is overnight parking was $68/night.

Reviewed on Jun 9, 2026

Landing Furnished Apartments Near Northside

Landing Furnished Apartments Near Northside

4 out of 5
Near Northside
Price was CA $1,651, price is now CA $1,387 per person
CA $1,387
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Indianapolis (IND)
9.6/10 Exceptional! (5 reviews)
Le Méridien Indianapolis

Le Méridien Indianapolis

4 out of 5
Downtown Indianapolis
Price was CA $2,213, price is now CA $1,868 per person
CA $1,868
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Indianapolis (IND)
9.2/10 Wonderful! (1,004 reviews)
As a frequent traveler, I plan to go back to the hotel. I had an excellent waiter Geoffrey that was very friendly and efficient. The food , room accommodations were excellent.The only thing is you must call ahead of time to reserve a table for the breakfast/ brunch. My suggestion to the front desk is to ask during check in is whether you want to dine there and if so ,to make a reservation. Also, to let people know if there is an event nearby due to changes for pickup for rides, such as an Uber. The frontable is still under construction which is unfortunate but I hope by the next time I arrive , it will be finished. Overall, I would give the hotel an A minus .

Reviewed on Jun 14, 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

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 $236 per night from Jul 3 to Jul 4
CA $236
CA $279 total
Jul 3 - Jul 4
includes taxes & fees
9.4/10 Exceptional! (1,078 reviews)
"The staff here was amazing. Its been a while since I've experienced so many helpful employees:)"

Reviewed on Jun 16, 2026

Omni Severin Hotel
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 $240 per night from Jun 21 to Jun 22
CA $240
CA $281 total
Jun 21 - Jun 22
includes taxes & fees
9.8/10 Exceptional! (1,965 reviews)
"This hotel is amazing from the moment you pull up, check in and walk into your room. Love the staff, decor, every part is special."

Reviewed on Jun 18, 2026

Ironworks Hotel Indy
Best Western Plus Indianapolis North at Pyramids

Best Western Plus Indianapolis North at Pyramids

3 out of 5
9320 N Michigan Rd Indianapolis IN
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jun 23 to Jun 24
CA $140
CA $163 total
Jun 23 - Jun 24
includes taxes & fees
8/10 Very Good! (1,022 reviews)
"The property was nice and clean, well maintained. Check in staff was friendly. My room was clean, the temperature control worked well and was not noisy, the refrigerator worked, the bed was comfortable, and the shower worked well and didn’t leak all over the floor. The complimentary breakfast was ..."

Reviewed on Jun 18, 2026

Best Western Plus Indianapolis North at Pyramids
See all 2,488 properties in Windermere
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 Windermere vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Windermere from just CA $1,339. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.