Exclusive Road America Vacation Deals

Road America vacation package deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Save 100% on your flight
Price was $435, price is now $271 per person
$271
per person
Feb 18 - Feb 23
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Save 100% on your flight
Price was $723, price is now $487 per person
$487
per person
Feb 18 - Feb 23
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $963, price is now $651 per person
$651
per person
Feb 18 - Feb 23
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
This smoke-free hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and a library are also on offer.
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 $630, price is now $428 per person
$428
per person
Feb 18 - Feb 23
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $707, price is now $494 per person
$494
per person
Feb 18 - Feb 23
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.
The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Save 100% on your flight
Price was $720, price is now $517 per person
$517
per person
Feb 18 - Feb 23
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, dry cleaning, and luggage storage are also on offer.

Frequently asked questions

How much are vacation packages to Road America?
If you like the sound of stress-free planning and great savings, our $271 Road America vacation package will be perfect for you. With your flights and hotels sorted, organizing your getaway around this amazing attraction has never been easier.
Where can I get the best vacation package deals for Road America?
Your dream escape is waiting for you at Travelocity. With access to 400 airline partners and a whopping 1,000,000 hotels all over the world, creating the perfect Road America package deal couldn't be easier.
Why should I purchase my Road America vacation bundle via Travelocity?
From exciting destinations to one-of-a-kind experiences, we have everything you need to satisfy your love for travel. Our 24/7 support will also make sure you're being well taken care of during your getaway. And don't panic if you find a better price on your booking, we'll match it. That's our Price Match Guarantee.

Top Road America hotel deals

The Osthoff Resort

The Osthoff Resort

3.5 out of 5
101 Osthoff Avenue Elkhart Lake WI
$251 nightly
The price is $283 total per night
$283 total
Dec 26 - Dec 27
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Siebkens Resort

Siebkens Resort

3 out of 5
284 S Lake St Elkhart Lake WI
$119 nightly
The price is $134 total per night
$134 total
Dec 26 - Dec 27
Total with taxes and fees
A private beach and a restaurant are featured at this hotel. Enjoy the seasonal outdoor pool and perks like free WiFi. There's a bar/lounge on site, and express check-out and wedding services are also provided.
On private beach
Pool
AmericInn by Wyndham Plymouth

AmericInn by Wyndham Plymouth

2 out of 5
1708 Eastern Ave Plymouth WI
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $105 total per night
$105 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a hot tub. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A business center, a lobby fireplace, and dry cleaning are also on offer.
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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.