Summit Vacation Packages

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

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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.
Landing Apartments at Mayfair Collection

Landing Apartments at Mayfair Collection

4 out of 5
Wauwatosa
Price was CA $1,799, price is now CA $1,617 per person
CA $1,617
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
10/10 Exceptional! (4 reviews)
Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!

Reviewed on May 21, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,746, price is now CA $1,836 per person
CA $1,836
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Staff were extremely friendly and helpful!

Reviewed on Jul 4, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,967, price is now CA $1,655 per person
CA $1,655
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.8/10 Exceptional! (2,645 reviews)
We loved the location and the "uniqueness" of this hotel. The staff was also some of the nicest we have ever encountered!! Thank you for a great stay, we will be back!!

Reviewed on Jul 4, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,978, price is now CA $1,687 per person
CA $1,687
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,176 reviews)
Beautiful property! I like the outdoor bar and restaurant on site. Rooms are very nice and very clean!. Comfortable beds.

Reviewed on Jul 4, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $2,042, price is now CA $1,847 per person
CA $1,847
per person
Aug 28 - Aug 31
found 20 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.4/10 Exceptional! (369 reviews)
Loved our stay! And want to go back!

Reviewed on Jun 30, 2026

Ready to book your vacation to Summit?

 

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Summit Hotel Deals

Waterfront Lake Cottage - Upper Nemahbin Lake

Waterfront Lake Cottage - Upper Nemahbin Lake

Oconomowoc WI
The price is CA $703 per night from Aug 3 to Aug 4
CA $703
CA $1,439 total
Aug 3 - Aug 4
includes taxes & fees
9.6/10 Exceptional! (32 reviews)
"The entire process of renting this house was easy and streamlined. The hosts and the property itself were top notch. Highly recommend!"

Reviewed on Jun 9, 2026

Waterfront Lake Cottage - Upper Nemahbin Lake
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 $134 per night from Jul 5 to Jul 6
CA $134
CA $154 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (933 reviews)
"The hotel staff were very friendly and helpful. Great customer service. The hotel itself was clean and well maintained. Having both an indoor and outdoor pool was very nice!"

Reviewed on Jul 4, 2026

Sheraton Milwaukee Brookfield Hotel
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Jul 13 to Jul 14
CA $124
CA $144 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very good! (1,375 reviews)
"Convenient location"

Reviewed on Jul 3, 2026

AmericInn by Wyndham Brookfield
See all 377 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Stay near popular Summit attractions

Lower Nemahbin Lake

Commune with nature and explore the great outdoors at Lower 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 $1,617 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.

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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.