Darlington Vacations from $492

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The Latest Darlington vacation packages

Price found within the past 48 hours. Click for updated prices.
Edge-O-Dells Resort - 21 and Older

Edge-O-Dells Resort - 21 and Older

2.5 out of 5
Price was $601, price is now $492 per person
$492
per person
Jul 31 - Aug 5
found 19 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
8.8/10 Excellent! (459 reviews)
They had a problem with the Internet I didn’t have for a little over a day so I called. They sent somebody to fix it then this morning I went to turn on the TV same issue. I rebooted the box like I was shown by staff and it did not work so that was frustrating and the room smelled very musky and almost like mildewy.

Reviewed on May 26, 2026

Dellshire Resort

Dellshire Resort

3.5 out of 5
Price was $827, price is now $706 per person
$706
per person
Aug 4 - Aug 8
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
8.6/10 Excellent! (37 reviews)
If you don't want a half hour walk from the parking lot to your room, don't stay here. Need escalators for real.

Reviewed on Jun 16, 2026

All Star Inn & Suites

All Star Inn & Suites

2 out of 5
Price was $602, price is now $526 per person
$526
per person
Aug 4 - Aug 8
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
9/10 Wonderful! (747 reviews)
Just stopped for the night passing through. Room was ok. Pillows smelled funny but looked clean. Great that it is pet friendly!

Reviewed on Jun 15, 2026

Courtyard by Marriott Madison East

Courtyard by Marriott Madison East

3 out of 5
Price was $619, price is now $547 per person
$547
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (672 reviews)
Wish there was a microwave in the room..

Reviewed on Jun 14, 2026

Hotel Ruby Marie

Hotel Ruby Marie

3 out of 5
Downtown Madison
Price was $717, price is now $634 per person
$634
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9.4/10 Exceptional! (1,005 reviews)
The Hotel is like the old railroad hotel it probably used to be except with larger rooms, wonderful amenities, very clean, and comfy bed. Its decor is like the early 1900’s - you’ll enjoy looking at the photos and artifacts. Rosalina served a good breakfast at the street level cafe. There is a large, busy intersection including a train crossing out front but I was not bothered by traffic nor trains (I think 2 came thru.) I had a view of one of the lakes across the street. Highly recommend this delightful stay.

Reviewed on Jun 17, 2026

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Darlington Hotel Deals

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
$101 nightly
The price is $112 total per night from Jun 30 to Jul 1
$112 total
Jun 30 - Jul 1
Total with taxes and fees
Wyndham Garden Galena Hotel & Day Spa
Irish Cottage Inn & Suites

Irish Cottage Inn & Suites

3.5 out of 5
9853 US-20 Galena IL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Jun 21 to Jun 22
$125 total
Jun 21 - Jun 22
Total with taxes and fees
9.4/10 Exceptional! (1,378 reviews)
"Breakfast menu was fresh but pancakes were not hot. Tea was a pleasant bonus. Dinner was good and entertainment was nice surprise. Overall very pleasant stay and would book again."

Reviewed on Jun 16, 2026

Irish Cottage Inn & Suites
Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
940 Galena Square Dr Galena IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Jun 29 to Jun 30
$98 total
Jun 29 - Jun 30
Total with taxes and fees
9.4/10 Exceptional! (1,335 reviews)
"Our stay at Stoney Creek Inn - Galena was good. The Main Street shops are just over a mile away, so location was good. The hotel is clean but in major need of some updates. The rooms and especially the breakfast area were really dark. Carpet is coming up in areas and the couch in our suite had a ..."

Reviewed on Jun 15, 2026

Stoney Creek Inn Galena
See all 716 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 $492 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.