Darlington Vacations from $309

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The Latest Darlington vacation packages

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

3 out of 5
Price was $425, price is now $309 per person
$309
per person
Jan 9 - Jan 12
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
8.4/10 Very Good! (121 reviews)
All was great and will come back again

Reviewed on Sep 29, 2025

Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
Price was $598, price is now $459 per person
$459
per person
Jan 9 - Jan 12
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
8.2/10 Very Good! (1,003 reviews)
I was supposed to have access to a patio and due to construction did not. Everything is dated and the pools don’t look clean.

Reviewed on Oct 18, 2025

Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $479, price is now $368 per person
$368
per person
Dec 14 - Dec 17
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9/10 Wonderful! (71 reviews)
Very clean facilities. Very clean cabins. Top notch !

Reviewed on Nov 9, 2025

Club Wyndham Tamarack

Club Wyndham Tamarack

3.5 out of 5
Price was $410, price is now $328 per person
$328
per person
Jan 9 - Jan 12
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
9.2/10 Wonderful! (19 reviews)
This place far exceeded are expectations. Little hard to find our building in the subdivision at night but the property, location and room was really great! We are sharing our experience and will definitely do this again!

Reviewed on Feb 24, 2025

The Wisconsin Hotel & Conference Center

The Wisconsin Hotel & Conference Center

2.5 out of 5
Price was $447, price is now $362 per person
$362
per person
Jan 9 - Jan 12
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
9.4/10 Exceptional! (103 reviews)
Beautiful Hotel!!! Cant wait to come back.

Reviewed on Nov 12, 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
$80 nightly
The price is $88 total per night from Nov 16 to Nov 17
$88 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (430 reviews)
The room was very clean and lots of room to move around.

Reviewed on Nov 9, 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 Nov 24 to Nov 25
$109 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (1,273 reviews)
Check in was extremely easy & staff was fun & inviting

Reviewed on Nov 10, 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
$88 nightly
The price is $98 total per night from Nov 30 to Dec 1
$98 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (946 reviews)
Room was updated, clean and comfortable. Staff was kind and helpful. Breakfast was mediocre. The location was perfect.

Reviewed on Nov 7, 2025

Wyndham Garden Galena Hotel & Day Spa
See all 714 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 $309 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.

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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.