Summit 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*

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

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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.
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,544, price is now CA $1,382 per person
CA $1,382
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,702, price is now CA $1,441 per person
CA $1,441
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $1,694, price is now CA $1,552 per person
CA $1,552
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.4/10 Exceptional! (444 reviews)
Nice hotel downtown. Never talked to a person did everything by text which ended up being super useful because we came in late and left early. The code works great gets you in and out and very convenient. Rooms were wonderful and the hotel is centrally located. Loved it.

Reviewed on Nov 5, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,739, price is now CA $1,598 per person
CA $1,598
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,816 reviews)
Love it

Reviewed on Nov 7, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,560, price is now CA $1,439 per person
CA $1,439
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.8/10 Exceptional! (2,742 reviews)

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Summit Hotel Deals

Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Oconomowoc WI
9.4/10 Exceptional! (22 reviews)
"Great house"

Reviewed on Oct 5, 2026

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Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!
Beautiful Historic Tudor Mansion with sandy Private Beach

Beautiful Historic Tudor Mansion with sandy Private Beach

Oconomowoc WI
9.6/10 Exceptional! (44 reviews)
"This estate is absolutely gorgeous. The pictures do not do it justice, as I was blown away at the enormous size of the rooms (bedrooms, conservatory, kitchen, multiple dining areas and sitting rooms). My daughter got married this past Saturday, and we chose to rent Wildwood Estate instead of everyone ..."

Reviewed on Aug 31, 2026

Get rates
Beautiful Historic Tudor Mansion with sandy Private Beach
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Nov 15 to Nov 16
CA $123
CA $142 total
Nov 15 - Nov 16
includes taxes & fees
8.4/10 Very good! (1,334 reviews)
"Staff was not friendly and not helpful especially in the restaurant and bar and front desk. There is no business area to print a boarding pass and they refused to print it for me from the front desk. Hotel is dated vents in room are rusty room was not vacuumed before my arrival and garbage was not ..."

Reviewed on Nov 7, 2026

Sheraton Milwaukee Brookfield Hotel
See all 380 properties in Summit
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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Stay near popular Summit attractions

Upper Nemahbin Lake

Commune with nature and explore the great outdoors at Upper Nemahbin Lake during your travels in Summit.
See properties

Frequently asked questions

How much does a Summit vacation package cost?
You'll find cheap prices from CA $1,382 on Expedia for your Summit escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Summit costs.
What are the cheapest months to go to Summit?
January, February and March are great times to search for cheap Summit vacation packages. Opting to travel in quieter months means you can typically find lower prices on flights and hotels.
How many days is enough for Summit?
We'd recommend booking a Summit vacation for a minimum of 2 days. This will give you enough time to check off top sights including Oconomowoc Historical Museum and Fowler Lake Park, as well as explore neighbourhoods like Summit Corners and Maplewood. You could even slot in a day trip from Summit.
How to find the best Summit package deals?
Use Expedia's handy filters to help you find some fabulous Summit package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Summit package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Summit vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights separately. Better still, you can personalize your Summit escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Summit?
If you're considering a spontaneous Summit trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Summit?

  1. Pick your dates: What you plan to do in Summit and your favourite season can help you decide when to travel.
  2. Plan your budget wisely: Besides the price of your hotel, you should factor in other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that could arise during your trip to Summit.
  3. Decide how long to go away for: Now that you're more familiar with Summit, you can figure out the right length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Summit vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.