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 15 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 13 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 13 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 13 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 13 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 13 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.
Pool
Hot Tub
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.
Pool
Hot Tub
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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.