Sussex Vacations from $624

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Your Sussex Vacation

From its highlights to its hidden gems, this city is best explored with a Sussex vacation package. Find somewhere to stay in Halls Park, which is great for nature, watersports and views. Fill your trip to Sussex with visits to some of its big-ticket attractions. Where to first? You won't want to miss Sussex Bowl. Don't put off exploring this city any longer. Your perfect Sussex vacation is a few clicks away with Expedia.

The Latest Sussex vacation packages

Price found within the past 48 hours. Click for updated prices.
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
Price was $767, price is now $624 per person
$624
per person
Dec 5 - Dec 11
found 10 hours ago
Roundtrip flight included
Tampa (TPA) to Milwaukee (MKE)
8.6/10 Excellent! (981 reviews)
It was just ok

Reviewed on Oct 31, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,061, price is now $793 per person
$793
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)

Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 out of 5
Downtown Milwaukee
Price was $858, price is now $697 per person
$697
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,000 reviews)

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $892, price is now $735 per person
$735
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)
I really liked the property but the bar was a little pricey over $40 for two drinks

Reviewed on Oct 30, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $958, price is now $801 per person
$801
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.4/10 Exceptional! (444 reviews)
Absolutely loved our stay. The location is perfect and close to everything. The room is beautiful and I love the big common space. It was perfect to watch a Packer game with friends and then enjoy breakfast in the morning. The staff are so friendly and helpful and check-in and out were a breeze. Highly recommend and can’t wait to stay again.

Reviewed on Oct 31, 2026

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Sussex Hotel Deals

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $117 total per night from Nov 23 to Nov 24
$117 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,565 reviews)
"Nice hotel, friendly staff. Only negative is that while housekeeping came to drop off more bottles of water that we would be charged for if opening, The didn't bother to even remake our bed. I didn't expect new linens, but I would at minimum expect the bed remade of they intruded into my room."

Reviewed on Oct 30, 2026

Hyatt Regency Milwaukee
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
$87 nightly
The price is $100 total per night from Nov 8 to Nov 9
$100 total
Nov 8 - Nov 9
Total with taxes and fees
Sheraton Milwaukee Brookfield Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $131 total per night from Nov 30 to Dec 1
$131 total
Nov 30 - Dec 1
Total with taxes and fees
Drury Plaza Hotel Milwaukee Downtown
See all 1,250 properties in Sussex
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 Sussex Vacation Packages

Sussex Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Population
10,800
Top Sights
Sussex Bowl, Oconomowoc Golf Club and Maple Wayside Trailhead

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Frequently asked questions

How much does a Sussex vacation package cost?
You can pick up a vacation package to this destination from $624 on Expedia. But how much your vacation to Sussex costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Sussex?
You can usually find reduced prices and greater availability in November, December and January. Check out our cheap Sussex vacation packages and you could land some excellent off-season deals.
How many days is enough for Sussex?
With a well-planned itinerary, you can easily tick off the most popular Sussex sights in a handful of days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Sussex vacation for longer.
How to find the best Sussex package deals?
Begin your search for a Sussex package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Sussex package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sussex escape underway.
Is it cheaper to book a Sussex vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Sussex trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Sussex?
Enjoy fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Sussex escape.
Does Expedia offer Book Now, Pay Later Sussex vacation packages?
Your Sussex break should be an escape from your daily routine, not a source of money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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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.