Darlington Vacations from $574

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The Latest Darlington vacation packages

Price found within the past 48 hours. Click for updated prices.
Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $705, price is now $574 per person
$574
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9/10 Wonderful! (543 reviews)
Clean room, incredible staff, bartender made great drinks

Reviewed on May 16, 2026

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Save 100% on your flight
Price was $1,602, price is now $1,179 per person
$1,179
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.2/10 Wonderful! (1,001 reviews)
Prepare for lake flies/gnats! Could not open our window because there wasn’t a screen. Not sure if it was just the time of year (mid May).

Reviewed on May 17, 2026

Hotel Ruby Marie

Hotel Ruby Marie

3 out of 5
Downtown Madison
Price was $922, price is now $741 per person
$741
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.4/10 Exceptional! (1,008 reviews)
Just FYI, Room 11 faces the train tracks and the train WILL wake you up in the morning. Best alarm clock ever. I was very delightfully surprised how well maintained the hotel is and how nice the room was.

Reviewed on May 8, 2026

Fairfield Inn & Suites by Marriott Madison East

Fairfield Inn & Suites by Marriott Madison East

3 out of 5
Price was $815, price is now $658 per person
$658
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.2/10 Wonderful! (1,000 reviews)
Toilet didn't work well, hvac didn't work well, internet tv didn't work well.

Reviewed on Apr 26, 2026

Courtyard by Marriott Madison East

Courtyard by Marriott Madison East

3 out of 5
Price was $809, price is now $654 per person
$654
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9/10 Wonderful! (664 reviews)
Nice clean very amazing palce

Reviewed on Apr 12, 2026

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Darlington Hotel Deals

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
$110 nightly
The price is $122 total per night from May 20 to May 21
$122 total
May 20 - May 21
Total with taxes and fees
9.4/10 Exceptional! (1,339 reviews)
"The room was clean but they could update the pillows. Too saoft and lumpy. The chairs in the room are not comfortable; very hard. Breakfast was okay, typical hotel breakfast. The bartenders were great in the pub, live music was good."

Reviewed on May 17, 2026

Irish Cottage Inn & Suites
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
$79 nightly
The price is $87 total per night from May 25 to May 26
$87 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,144 reviews)
"Friendly staff, nice rooms."

Reviewed on May 17, 2026

Wyndham Garden Galena Hotel & Day Spa
Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
940 Galena Square Dr Galena IL
Fully refundable
$88 nightly
The price is $98 total per night from May 31 to Jun 1
$98 total
May 31 - Jun 1
Total with taxes and fees
9.2/10 Wonderful! (1,338 reviews)
"All Good"

Reviewed on May 17, 2026

Stoney Creek Inn Galena
See all 723 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 $574 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.