Darlington Vacations from $280

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The Latest Darlington vacation packages

Price found within the past 48 hours. Click for updated prices.
Thunderbird Motor Inn Baraboo

Thunderbird Motor Inn Baraboo

2 out of 5
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
7.8/10 Good! (452 reviews)
Pretty nice all around, recently painted and appears it has new flooring. Good experience, minimal noise. Only slept and showered for the 2 nights, beds are pretty average, pillows are actually pretty good! Water pressure is GREAT.

Reviewed on Jul 11, 2025

Bluegreen Odyssey Dells

Bluegreen Odyssey Dells

3.5 out of 5
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9.4/10 Exceptional! (127 reviews)
Friendly staff. Very accommodating.

Reviewed on Jul 3, 2025

Comfort Suites Madison West - Middleton

Comfort Suites Madison West - Middleton

2.5 out of 5
per person
Aug 27 - Aug 31
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
8/10 Very Good! (353 reviews)
We went for the pool, but a child pooped in it, so pool was shut down from 11am Saturday until we left 11am Sunday. Online, it says all they had to do was remove feces and shock water with chemicals and recirculate clean water, 2 hours. Why did nothing get cleaned in over 24 hours?

Reviewed on Jul 11, 2025

AmericInn & Suites By Wyndham Baraboo Event Center

AmericInn & Suites By Wyndham Baraboo Event Center

2.5 out of 5
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
7.8/10 Good! (1,004 reviews)
Efficient and quick check in.

Reviewed on Jul 6, 2025

La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton

La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton

3 out of 5
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9/10 Wonderful! (1,077 reviews)
It was a great, quick stay. Minutes from all the water fun at the Dells.

Reviewed on Jul 7, 2025

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Darlington Hotel Deals

Darlington Inn
Darlington Inn
2 out of 5
201 Christiensen Dr, Darlington, WI
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Jul 20 to Jul 21
$86 total
Jul 20 - Jul 21
Total includes taxes and fees
8.4/10 Very Good! (401 reviews)
Couple's weekend
"The hotel was perfect for what we needed. Close enough from Madison and at a good rate. The only thing is that the hotel doesn't have an elevator, if you are unable to walk stairs you would need to tell them when you book for 1st floor room. Breakfast was good. Staff was super accommodating and let ..."

Reviewed on Jul 2, 2025

Darlington Inn
Stoney Creek Inn Galena
Stoney Creek Inn Galena
2 out of 5
940 Galena Square Dr, Galena, IL
Fully refundable
$98 nightly
The price is $109 total per night from Jul 15 to Jul 16
$109 total
Jul 15 - Jul 16
Total includes taxes and fees
9.2/10 Wonderful! (1,196 reviews)
"This is an outstanding motel. A custom feel throughout with theme lamps and other touches that show refined taste. A gem. Highly recommended."

Reviewed on Jul 11, 2025

Stoney Creek Inn Galena
Wyndham Garden Galena Hotel & Day Spa
Wyndham Garden Galena Hotel & Day Spa
4 out of 5
11383 US Highway 20, Galena, IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $96 total per night from Jul 28 to Jul 29
$96 total
Jul 28 - Jul 29
Total includes taxes and fees
9.2/10 Wonderful! (735 reviews)
"The gardenview off the deck was spectacular! Really enjoyed my stay!"

Reviewed on Jul 10, 2025

Wyndham Garden Galena Hotel & Day Spa
See all 687 properties in Darlington
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 Darlington Vacation Packages

Darlington Essential Information

Language
English
Currency
U.S dollars
Population
2,400
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Yellowstone Lake State Park, Mineral Point Railroad Museum and Badger Mine and Museum

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Frequently asked questions

How much does a Darlington vacation package cost?
Offering great value package deals from $280 on Expedia, you'll be thrilled with how little a vacation to Darlington costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Darlington?
September, November and December are great times to search for cheap Darlington vacation packages. Opting to travel in quieter periods means you can generally find better prices on hotels and flights.
How many days is enough for Darlington?
Typically, a handful of days is enough to go to the top sights during your Darlington vacation. However, if you prefer to have more time to unwind or take day tours, think about extending your trip.
How to find the best Darlington package deals?
Begin your search for a Darlington package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Darlington package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Darlington getaway off to a flying start.
Is it cheaper to book a Darlington vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Darlington vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Darlington?
If you're planning an impromptu Darlington trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Darlington vacation packages?
Your Darlington getaway is meant to be an escape from your daily routine, not a source of money worries. So to give you that extra flexibility, we've teamed 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 cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.