Fennimore Vacation Packages

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Your Fennimore Vacation

When a city break is calling your name, answer it with a Fennimore vacation package. With all your travel plans in place before you go, all you need to do here is concentrate on having a ball. Every trip to Fennimore needs a well-designed itinerary. Fill yours with leading attractions like Whispering Winds Winery, Fennimore Doll and Toy Museum and Fennimore Railroad Historical Society Museum. Browse Expedia's wide range of travel options and start planning your perfect vacation to Fennimore now.

Top Fennimore Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Valued Stay Sun Prairie

Valued Stay Sun Prairie

2.5 out of 5
Price was CA $1,075, price is now CA $1,036 per person
CA $1,036
per person
Dec 20 - Dec 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
7.2/10 Good! (627 reviews)

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was CA $1,358, price is now CA $1,279 per person
CA $1,279
per person
Dec 20 - Dec 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (1,008 reviews)

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 $1,240, price is now CA $1,184 per person
CA $1,184
per person
Dec 20 - Dec 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (4,264 reviews)
Awesome gym, pool with hot hotub and an amazing sauna that I used every night before bed. The Governor’s club is worth the cost without a doubt. I highly recommend.

Reviewed on Nov 9, 2026

Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
Downtown Madison
Price was CA $1,202, price is now CA $1,150 per person
CA $1,150
per person
Dec 20 - Dec 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.6/10 Exceptional! (1,006 reviews)

Hyatt Place Madison Downtown

Hyatt Place Madison Downtown

3 out of 5
Downtown Madison
Price was CA $1,244, price is now CA $1,197 per person
CA $1,197
per person
Dec 20 - Dec 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (1,003 reviews)
Great property with parking attached. Staff was friendly and helpful.

Reviewed on Nov 9, 2026

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Fennimore Hotel Deals

Fenway House Hotel

Fenway House Hotel

2.5 out of 5
1096 Lincoln Ave Fennimore WI
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Nov 10 to Nov 11
CA $155
CA $164 total
Nov 10 - Nov 11
includes taxes & fees
9.2/10 Wonderful! (112 reviews)
"Cool retro hotel downtown. Very helpful owners."

Reviewed on Nov 7, 2026

Fenway House Hotel
Napps Motel

Napps Motel

2 out of 5
645 12TH ST HWY 18 EAST Fennimore WI
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Nov 10 to Nov 11
CA $88
CA $96 total
Nov 10 - Nov 11
includes taxes & fees
Napps Motel
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!

Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!

Fennimore WI
10/10 Exceptional! (120 reviews)
"Great place. Gorgeous setting"

Reviewed on Oct 26, 2026

Get rates
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
See all 117 properties in Fennimore
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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Stay near popular Fennimore attractions

Fennimore Doll and Toy Museum

8.0/10 (7 reviews)
You can spend time browsing the exhibits at Fennimore Doll and Toy Museum in Fennimore. Discover the area's live music and monuments.
See properties

Frequently asked questions

How much does a Fennimore vacation package cost?
You'll find cheap prices from CA $1,036 on Expedia for your Fennimore getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Fennimore costs.
What are the cheapest months to go to Fennimore?
The off-season is the best time to travel to Fennimore if you're on a budget. Another tip for finding cheap Fennimore vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Fennimore?
The ideal duration for your Fennimore vacation depends on what you'd like to see. Typically, a few days to a week will give you time to hit all the major sights and discover some hidden spots along the way.
How to find the best Fennimore package deals?
Begin your search for a Fennimore package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Fennimore package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Fennimore escape underway.
Is it cheaper to book a Fennimore vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Fennimore vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Fennimore?
If you have your Fennimore travel dates finalized, book as soon as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Fennimore?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Fennimore.
  2. Budget wisely: On top of the price of your accommodations, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Fennimore.
  3. Decide how many days away: Start by listing all the attractions and activities you want to experience in Fennimore. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Fennimore vacation package.

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