Darlington Vacations from $688

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 $855, price is now $688 per person
$688
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Madison (MSN)
9/10 Wonderful! (511 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
Price was $1,144, price is now $902 per person
$902
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Madison (MSN)
9.4/10 Exceptional! (55 reviews)
We all loved everything about the property, but I wanted to let you know that our room did have ants when we walked in and throughout our stay.

Reviewed on Aug 9, 2025

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $960, price is now $760 per person
$760
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Madison (MSN)
8.6/10 Excellent! (1,002 reviews)
WiFi was terrible, very slow

Reviewed on Aug 12, 2025

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
Price was $1,022, price is now $822 per person
$822
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Madison (MSN)
9.4/10 Exceptional! (2,992 reviews)
Great location. Convenient transportation from airport and around city. Very nice common areas. Room service for breakfast was timely and very good. I received no benefit for VIP access, even though upgrade to Governor's Club was available. Didn't seem 5 star if you were not part of Governor's Club. The rooms have very little toiletries. There is no water. They do not clean the hotel rooms unless you stay three nights.

Reviewed on Aug 23, 2025

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $923, price is now $743 per person
$743
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Madison (MSN)
9/10 Wonderful! (1,000 reviews)
Clean facilities, friendly staff, quiet, great location.

Reviewed on Aug 3, 2025

Don't see what you're looking for?
See all available trips from Columbus to Darlington
View all trips

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 Aug 31 to Sep 1
$86 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (409 reviews)
"The hot tub was down for maintenance when we were there"

Reviewed on Aug 20, 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 Aug 25 to Aug 26
$109 total
Aug 25 - Aug 26
Total with taxes and fees
9.2/10 Wonderful! (1,210 reviews)
"Loved this Inn! Super rustic feel and clean!"

Reviewed on Aug 18, 2025

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
$106 nightly
The price is $118 total per night from Aug 25 to Aug 26
$118 total
Aug 25 - Aug 26
Total with taxes and fees
9.4/10 Exceptional! (1,174 reviews)
"We really enjoyed the whole vibe. The bar was a bit pricey, but has an amazing feel. It served us very well as a home base in our stay in Galena, and had us within short drives to all the places we wanted to visit. Potosi, Dubuque, Effegy Mounds and of course downtown Galena."

Reviewed on Aug 21, 2025

Irish Cottage Inn & Suites
See all 698 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Darlington vacation package cost?
Offering great value package deals from $688 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.