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A forest with yellow autumn leaves and fallen branches.

Eastside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

The Latest Eastside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Indoor pool, outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
    Oct 19 - Oct 22

    Fourwinds Lakeside Inn & Marina + Flight

    Bloomington
    3 nights
    3.0 star property
    8.2/10 - Very good (847 reviews)
    Roundtrip • Toronto (YYZ) - Indianapolis (IND)
    YYZ - IND • 1 stop IND - YYZ • 1 stop
    CA $1,213
    CA $1,059
    per traveller
    found 10 hours ago
    Fourwinds Lakeside Inn & Marina
  • House
    Oct 19 - Oct 22

    Two Lakefront Cabins Next Door + Flight

    Martinsville
    3 nights
    2.0 star property
    Roundtrip • Toronto (YYZ) - Indianapolis (IND)
    YYZ - IND • 1 stop IND - YYZ • 1 stop
    CA $3,638
    CA $3,113
    per traveller
    found 10 hours ago
    Two Lakefront Cabins Next Door
  • Bar (on property)
    Sept 20 - Sept 24

    Hilton Garden Inn Bloomington + Flight

    Downtown Bloomington
    4 nights
    3.0 star property
    8.6/10 - Excellent (1,001 reviews)
    "Nice and easy walk to everywhere in bloomington"
    Reviewed July 30, 2026
    Roundtrip • Calgary (YYC) - Indianapolis (IND)
    YYC - IND • 1 stop IND - YYC • 1 stop
    CA $1,321
    CA $1,136
    per traveller
    found 1 day ago
    Hilton Garden Inn Bloomington
  • House, Accessible
    Oct 19 - Oct 22

    Private Retreat w Pool Hot Tub and Dining Hall + Flight

    Bloomington
    3 nights
    2.0 star property
    Roundtrip • Toronto (YYZ) - Indianapolis (IND)
    YYZ - IND • 1 stop IND - YYZ • 1 stop
    CA $2,673
    CA $2,350
    per traveller
    found 10 hours ago
    Private Retreat w Pool Hot Tub and Dining Hall
  • House
    Oct 19 - Oct 22

    Lakefront Hot tub Amazing Views 35 min to Indy + Flight

    Martinsville
    3 nights
    2.0 star property
    Roundtrip • Toronto (YYZ) - Indianapolis (IND)
    YYZ - IND • 1 stop IND - YYZ • 1 stop
    CA $2,280
    CA $2,038
    per traveller
    found 10 hours ago
    Lakefront Hot tub Amazing Views 35 min to Indy

Eastside Hotel Deals

Front of property - evening/night

Showers Inn

Showers Inn
4.0 star property
Old Northeast Downtown, 2.1 km from Eastside
9.8 out of 10, Exceptional, (561 reviews)
The price is CA $199
CA $223 total
includes taxes & fees
Aug 10 - Aug 11
Showers Inn
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.
See all properties in Eastside
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.