Darlington Vacation Packages

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Top Darlington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
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 CA $1,318, price is now CA $1,231 per person
CA $1,231
per person
Nov 14 - Nov 16
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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

Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was CA $1,504, price is now CA $1,361 per person
CA $1,361
per person
Nov 14 - Nov 16
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (511 reviews)
Great location along the lake and trails

Reviewed on Aug. 10, 2025

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was CA $1,525, price is now CA $1,413 per person
CA $1,413
per person
Nov 14 - Nov 16
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9.2/10 Wonderful! (1,002 reviews)
Lightning in Bathroom was not very good

Reviewed on Aug. 19, 2025

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was CA $1,367, price is now CA $1,268 per person
CA $1,268
per person
Nov 14 - Nov 16
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (1,000 reviews)
Clean facilities, friendly staff, quiet, great location.

Reviewed on Aug. 3, 2025

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was CA $1,431, price is now CA $1,342 per person
CA $1,342
per person
Nov 14 - Nov 16
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.6/10 Excellent! (1,002 reviews)
WiFi was terrible, very slow

Reviewed on Aug. 12, 2025

Ready to book your vacation to Darlington?

 

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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
The price is CA $109 per night from Aug 24 to Aug 25
CA $109
CA $119 total
Aug 24 - Aug 25
includes taxes & 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 refundableReserve now, pay when you stay
The price is CA $136 per night from Aug 24 to Aug 25
CA $136
CA $151 total
Aug 24 - Aug 25
includes taxes & 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
The price is CA $113 per night from Aug 25 to Aug 26
CA $113
CA $164 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (1,175 reviews)
"Great location and great food! Staff was exceptional and attentive."

Reviewed on Aug. 20, 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.
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Frequently asked questions

How much does a Darlington vacation package cost?
You'll find cheap prices from CA $1,231 on Expedia for your Darlington escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Darlington costs.
What are the cheapest months to go to Darlington?
You can generally find lower prices and greater availability in March, November and December. Explore our cheap Darlington vacation packages and you could land some great off-season discounts.
How many days is enough for Darlington?
With a well-organized travel plan, you can easily hit the top Darlington sights in a few days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Darlington vacation for longer.
How to find the best Darlington package deals?
Start your search for a Darlington package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Darlington package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Darlington adventure off to a flying start.
Is it cheaper to book a Darlington vacation as a package?
You can enjoy significant savings on your next Darlington getaway by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Darlington?
If you've got your Darlington travel dates finalized, book early to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Darlington?

  1. Pick your dates: The things you plan to do in Darlington and your favourite season will help you decide when to get away.
  2. Budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that may come up during your trip to Darlington.
  3. Work out your trip length: Consider how much time you want to spend discovering Darlington. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Darlington vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.