Windermere Vacations from $582

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Your Windermere Vacation

Take the stress and hassle out of organizing your next adventure by booking a Windermere vacation package. Soak in the sounds and sights of this captivating neighborhood and enjoy what it has to offer. Kick off your trip to Windermere with a visit to nearby attractions such as Topgolf, Nickel Plate District Amphitheater and Sky Zone Sports. Whatever your dream Windermere vacation looks like, you can turn it into reality with Expedia.

The Latest Windermere Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Indianapolis Airport

Home2 Suites by Hilton Indianapolis Airport

3 out of 5
Price was $757, price is now $582 per person
$582
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
9.2/10 Wonderful! (403 reviews)
The room was clean and tidy, and the staff were very warm and courteous. A shuttle bus to the airport runs at 3:30 AM. I absolutely loved this place and highly recommend it.

Reviewed on Oct 12, 2025

Fairfield Inn & Suites by Marriott Indianapolis Carmel

Fairfield Inn & Suites by Marriott Indianapolis Carmel

2.5 out of 5
Price was $803, price is now $588 per person
$588
per person
Dec 28 - Jan 2
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
9.6/10 Exceptional! (561 reviews)
The hotel was very clean, comfy bed and super accommodating staff. The bathroom, especially the shower was so well designed.

Reviewed on Oct 4, 2025

Hilton Garden Inn Indianapolis Airport

Hilton Garden Inn Indianapolis Airport

3 out of 5
Price was $833, price is now $617 per person
$617
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
8.8/10 Excellent! (522 reviews)
Good price for the location. Friendly staff! Nice room

Reviewed on Oct 12, 2025

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was $925, price is now $699 per person
$699
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
9/10 Wonderful! (309 reviews)
Convenient for Pacer/Fever games

Reviewed on Oct 8, 2025

Embassy Suites by Hilton Indianapolis Downtown

Embassy Suites by Hilton Indianapolis Downtown

3.5 out of 5
Downtown Indianapolis
Price was $924, price is now $697 per person
$697
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
8.4/10 Very Good! (1,011 reviews)
The complimentary breakfast was awesome! The staff were very friendly and helpful. Our room was clean and very accommodating during our stay. I would definitely recommend it to others!

Reviewed on Oct 6, 2025

Where to stay in Windermere

Find the best Windermere areas and neighborhoods for the activities you enjoy most. Learn more about Windermere
Central Canal which includes landscape views, a river or creek and a city

Downtown Indianapolis

5 out of top 10 points of interest in this area
4.5/5(2,481 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
$179 nightly
The price is $210 total per night from Oct 19 to Oct 20
$210 total
Oct 19 - Oct 20
Total with taxes and fees
9.6/10 Exceptional! (1,662 reviews)
"Loved this hotel, it was clean safe and such a unique place."

Reviewed on Oct 8, 2025

Ironworks Hotel Indy
Courtyard by Marriott Indianapolis Downtown

Courtyard by Marriott Indianapolis Downtown

3 out of 5
601 West Washington Street, Indianapolis, IN
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $160 total per night from Oct 17 to Oct 18
$160 total
Oct 17 - Oct 18
Total with taxes and fees
9/10 Wonderful! (1,031 reviews)
"Great Customer Service!"

Reviewed on Oct 10, 2025

Courtyard by Marriott Indianapolis Downtown
Hyatt Regency Indianapolis

Hyatt Regency Indianapolis

4 out of 5
One South Capitol Avenue, Indianapolis, IN
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $180 total per night from Nov 2 to Nov 3
$180 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Interior rooms are do for an upgrade, but the lobby and restaurants are nice. Hotel is a great location."

Reviewed on Oct 11, 2025

Hyatt Regency Indianapolis
See all 2,345 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Windermere

Downtown Indianapolis

Lucas Oil Stadium

4.5/5(891 reviews)

Admire the innovative redbrick design of this large arena and watch a game of professional football in the downtown district of Indianapolis.

Lucas Oil Stadium
Indianapolis Motor Speedway featuring interior views

Indianapolis Motor Speedway

4.5/5(515 reviews)

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

Indianapolis Motor Speedway
Indiana Convention Center which includes signage and flowers

Indiana Convention Center

4.5/5(555 reviews)

A multipart venue welcomes visitors to downtown Indianapolis for conference and trade events, exciting sports competitions and performing artist concerts.

Indiana Convention Center

Things to do

Indianapolis: Crossroads Ghosts Haunted Walking Tour

Wicked Wraiths of White River: Indianapolis Ghost Tour

$32
per adult
Wicked Wraiths of White River: Indianapolis Ghost Tour
Group with axes for throwing in Indianapolis

30-Minute Walk-In Axe Throwing Experience Indianapolis

$22
per adult
100% of travellers recommend
30-Minute Walk-In Axe Throwing Experience Indianapolis
Indianapolis: Open-Air Pedal Pub Tour

Indianapolis: Open-Air Pedal Pub Tour

$64
per adult
Indianapolis: Open-Air Pedal Pub 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.