Summit Vacation Packages
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Your Summit Vacation
Book a tailored Summit vacation package that has only the things you need and nothing you don't. Great for nature, watersports and views, consider basing yourself in the neighborhood of Halls Park. Any trip to Summit needs a well-thought-out itinerary. Fill yours with famous sights like Fowler Lake Park, Oconomowoc Arts Center and Oconomowoc Golf Club. Stop daydreaming and start adventuring. Browse the range of options on Expedia today and put your Summit vacation plans in motion!
Top Summit Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Milwaukee Airport by IHG
College Heights
Price was CA $1,390, price is now CA $1,123 per person
CA $1,123
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
8/10 Very Good! (975 reviews)
If the dryer is broken and at check in someone asks where the laundry room is at, you should probably mention the dryer is broken! Finding out hours aftet checking in that the dryer is broken is not the time to find out. We wouldve canceled our stay as we needed to wash cloths during our vacation.
Reviewed on Aug. 25, 2025
The Pfister Hotel
Downtown Milwaukee
Price was CA $1,908, price is now CA $1,544 per person
CA $1,544
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (1,707 reviews)
Historic, beautiful architecture and stunning interiors in the building. Also food and bar options.
Reviewed on Aug. 30, 2025
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was CA $1,951, price is now CA $1,580 per person
CA $1,580
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,397 reviews)
The hotel itself is unique and still the perfect room for comfort and cleanliness. Easy checkin with a glass of champagne. Loved the lobby bar with great bartenders. Great overall hotel close to many arts opportunities, but especially convenient when attending a show at Pabst Theater. Great experience!
Reviewed on Aug. 26, 2025
The Iron Horse Hotel
Fifth Ward
Price was CA $1,860, price is now CA $1,519 per person
CA $1,519
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Always an enjoyable stay @The Ironhorse.. Beds are uber comfortable , love the pillows !
Reviewed on Aug. 27, 2025
Hilton Milwaukee
Westown
Price was CA $1,688, price is now CA $1,387 per person
CA $1,387
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
8.4/10 Very Good! (1,061 reviews)
Our favorite thing about staying there were the adorable pups that greet you! My kids want to go back just for that reason! 😀
Reviewed on Aug. 18, 2025
Summit Hotel Deals
Waterfront Lake Cottage - Upper Nemahbin Lake
Oconomowoc
The price is CA $326 per night from Sep 8 to Sep 9
CA $326
CA $799 total
Sep 8 - Sep 9
includes taxes & fees
Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!
Oconomowoc
Sonesta Select Milwaukee Brookfield
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Sep 21 to Sep 22
CA $104
CA $121 total
Sep 21 - Sep 22
includes taxes & fees
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.
Discover the most popular places to visit in Summit
Fowler Lake Park
Explore the great outdoors at Fowler Lake Park, a lovely green space in Oconomowoc. Visit the shops or attend a sporting event in this family-friendly area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.