Stoughton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 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

Your Stoughton Vacation

Lock in a Stoughton vacation package and get set for an exciting adventure. Known for its rich history and lively atmosphere, there's lots to like about this captivating city. A trip to Stoughton is a wonderful opportunity to do some sightseeing. Be sure to look around well-known attractions like Stoughton Opera House, Lake Kegonsa State Park and Troll Beach. Expedia can help you escape your daily routine. Tailor your vacation to Stoughton to suit your travel style, whatever that may be.

Top Stoughton 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 1 day 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 1 day 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 1 day 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 1 day 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 1 day 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 Stoughton?

 

Choose your dates

Stoughton Hotel Deals

Days Inn by Wyndham Stoughton WI.

Days Inn by Wyndham Stoughton WI.

2 out of 5
1124 W. Main St., Stoughton, WI
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from Sep 14 to Sep 15
CA $82
CA $93 total
Sep 14 - Sep 15
includes taxes & fees
6.6/10 (300 reviews)
"Clean and comfortable and a good value compared with other nearby hotels. Typical breakfast options, both hot and cold; sitting area very clean and tidy. Would choose again for overall value."

Reviewed on Aug. 18, 2025

Days Inn by Wyndham Stoughton WI.
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
The price is CA $173 per night from Aug 31 to Sep 1
CA $173
CA $200 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (2,997 reviews)
"The only complaint was the long wait for the elevators!"

Reviewed on Aug. 21, 2025

The Madison Concourse Hotel and Governor's Club
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Aug 31 to Sep 1
CA $112
CA $129 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,189 reviews)
"Very clean with friendly staff."

Reviewed on Aug. 23, 2025

AmericInn by Wyndham Madison West
See all 513 properties in Stoughton
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Stoughton

Troll Beach

If a restful vacation is part of your travel plans, Troll Beach might be the perfect place to seek out during your trip to Stoughton. Amble around the area's lakeside or experience its musical theater.

Troll Beach

Frequently asked questions

How much does a Stoughton vacation package cost?
You can pick up a vacation package to this top destination from CA $1,231 on Expedia. However, how much your vacation to Stoughton costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Stoughton?
You can usually find lower prices and better availability in December, January and February. Explore our cheap Stoughton vacation packages and you could land some great off-season deals.
How many days is enough for Stoughton?
For your Stoughton vacation, a handful of days will be enough to tour all the highlights. Be sure to stop by Stoughton Opera House — it's one of the most popular sights in this destination. If you're looking for more adventure, consider basing yourself here and venturing off on some tours from Stoughton.
Is it worth booking a vacation package to Stoughton?
Boasting a host of highlights starting with its top-notch festivals, Stoughton is a good vacation destination. Whether you want to explore attractions like Stoughton Opera House and Troll Beach or take the path less travelled, you'll find loads to keep you busy during your Stoughton vacation.
How to find the best Stoughton package deals?
Use Expedia's filters to help you find some tempting Stoughton package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Stoughton package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Stoughton vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Stoughton vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Stoughton?
Land incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Stoughton trip.
How to plan a trip to Stoughton?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Stoughton.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your accommodations will likely be the largest expense during your trip to Stoughton.
  3. Decide how long to go away for: Now that you know more about Stoughton, you can figure out the right length of your vacation. Create a draft plan and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the perfect Stoughton vacation package for you.

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