Darlington Vacations from $585

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The Latest Darlington vacation packages

Price found within the past 48 hours. Click for updated prices.
MainStay Suites Fitchburg - Madison

MainStay Suites Fitchburg - Madison

2.5 out of 5
Price was $780, price is now $585 per person
$585
per person
Feb 24 - Mar 1
found 13 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
8.8/10 Excellent! (1,000 reviews)
The hotel and room were clean but furniture is dated. The breakfast was below average. Staff were nice. Location is convenient.

Reviewed on Jan 11, 2026

Madison Marriott South

Madison Marriott South

3.5 out of 5
Save 100% on your flight
Price was $1,149, price is now $810 per person
$810
per person
Feb 24 - Mar 1
found 13 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (524 reviews)
Great location along the lake and trails

Reviewed on Aug 10, 2025

The Saddlery Madison Downtown

The Saddlery Madison Downtown

2 out of 5
Downtown Madison
Save 100% on your flight
Price was $1,181, price is now $877 per person
$877
per person
Feb 24 - Mar 1
found 13 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9.4/10 Exceptional! (68 reviews)
Parking a little pricey and walls a bit thin when it comes to screaming children. Nice vibe though. Great location. Would definitely stay there again.

Reviewed on Dec 29, 2025

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
Save 100% on your flight
Price was $1,320, price is now $993 per person
$993
per person
Feb 24 - Mar 1
found 13 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9.4/10 Exceptional! (3,305 reviews)
Love the location, amenities and onsite restaurant

Reviewed on Jan 18, 2026

Bluegreen Odyssey Dells

Bluegreen Odyssey Dells

3.5 out of 5
Lake Delton
Price was $819, price is now $618 per person
$618
per person
Feb 23 - Feb 28
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Madison (MSN)
9.4/10 Exceptional! (159 reviews)
The staff at the establishment were very welcoming and accommodating, and Tyler in particular stood out for his friendly and helpful demeanor. He made our experience even more enjoyable and stress-free. We highly recommend this place for their exceptional staff and service.

Reviewed on Jan 11, 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
$84 nightly
The price is $93 total per night from Jan 25 to Jan 26
$93 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
Great room and staff!

Reviewed on Jan 14, 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
$80 nightly
The price is $89 total per night from Jan 19 to Jan 20
$89 total
Jan 19 - Jan 20
Total with taxes and fees
9.2/10 Wonderful! (1,301 reviews)
Room was very clean and the staff was very friendly.

Reviewed on Jan 4, 2026

Stoney Creek Inn Galena
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
$104 nightly
The price is $116 total per night from Jan 22 to Jan 23
$116 total
Jan 22 - Jan 23
Total with taxes and fees
9.4/10 Exceptional! (1,259 reviews)
the staff was accommodating and friendly. the room was very clean and well stocked.

Reviewed on Jan 6, 2026

Irish Cottage Inn & Suites
See all 710 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 $585 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.