Summit Vacations from $595

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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!

The Latest Summit vacation packages

Price found within the past 48 hours. Click for updated prices.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $784, price is now $595 per person
$595
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,179, price is now $836 per person
$836
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Very clean and modern. Walking distance to everything. Parking right next door

Reviewed on Jan 12, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $970, price is now $740 per person
$740
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Room ready early. Everything clean and well-kept. Will stay there again.

Reviewed on Jan 7, 2026

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was $1,069, price is now $817 per person
$817
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,001 reviews)
It would be very helpful clean daily the room

Reviewed on Jan 10, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $1,061, price is now $811 per person
$811
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Great hotel! So fun and unique. Very clean and personalized

Reviewed on Jan 11, 2026

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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.

Fowler Lake Park

Oconomowoc Historical Museum

You can spend time browsing the exhibits at Oconomowoc Historical Museum in Oconomowoc. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Historical Museum

Oconomowoc Golf Club

Enjoy a round of golf in Oconomowoc at Oconomowoc Golf Club. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Golf Club

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! (14 reviews)
It was very nice. Extremely spacious. Beautiful yard to enjoy. Appreciate the yard and inside games and toys. It's a great lake! Swimming & fishing both were great but a ladder up to the pier would've been helpful, and maybe another paddle board and kayak so they could double up. Reconfigured sleeping/ ...

Reviewed on Aug 19, 2025

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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! (36 reviews)
This has become an annual trip and this house is the staple of it. There are so many options, from the yard, to the pool/jacuzzi/hot tub, to the firepit and lake area for everyone to hang out and have a great time! Can't wait til next year!

Reviewed on Sep 8, 2025

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Beautiful Historic Tudor Mansion with sandy Private Beach
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Jan 19 to Jan 20
$85 total
Jan 19 - Jan 20
Total with taxes and fees
8/10 Very Good! (1,378 reviews)
Really nice people and the room was more then i expected for the price

Reviewed on Jan 10, 2026

Sonesta Select Milwaukee Brookfield
See all 346 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.

Find the Best Summit Vacation Packages

Summit Essential Information

Language
English
Currency
U.S dollars
Top Sights
Oconomowoc Historical Museum, Fowler Lake Park and Oconomowoc Golf Club

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Frequently asked questions

How much does a Summit vacation package cost?
Offering great value package deals from $595 on Expedia, you'll be surprised at how little a vacation to Summit costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Summit?
January, June and September are the best times to look for cheap Summit vacation packages. Choosing to travel in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Summit?
The ideal length for your Summit vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to check out all the leading sights and explore some hidden gems along the way.
How to find the best Summit package deals?
Bagging a cheap Summit package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most economical Summit package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Summit vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Summit escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Summit?
If you've got your Summit vacation dates finalized, book as soon as you can to score some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Summit vacation packages?
Your Summit getaway is meant to be an escape from your daily routine, not a reason for money-related stress. So to give you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Explore a world of travel with Expedia

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