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.
All Star Inn & Suites

All Star Inn & Suites

2 out of 5
Price was CA $1,070, price is now CA $958 per person
CA $958
per person
Aug 18 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (763 reviews)
Nice place. The room we were in was renovated and looked nice. My only complaint is there is a window in the back of the room by the ceiling with no curtain so it got very light in the room early in the morning, which kept waking me up. Kids enjoyed the outdoor pool. And we enjoyed the waterpark passes. Will look to stay here again!

Reviewed on Jul 7, 2026

Dellshire Resort

Dellshire Resort

3.5 out of 5
Price was CA $1,499, price is now CA $1,267 per person
CA $1,267
per person
Aug 18 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.8/10 Excellent! (96 reviews)
Great place for younger families.

Reviewed on Jul 8, 2026

Amber's Inn & Suites

Amber's Inn & Suites

2 out of 5
Downtown Wisconsin Dells
Price was CA $1,185, price is now CA $1,043 per person
CA $1,043
per person
Aug 18 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9.4/10 Exceptional! (1,003 reviews)
Quiet, peaceful and staff is always friendly.

Reviewed on Jul 6, 2026

Best Western Ambassador Inn & Suites

Best Western Ambassador Inn & Suites

2.5 out of 5
Price was CA $1,399, price is now CA $1,238 per person
CA $1,238
per person
Aug 18 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.6/10 Excellent! (1,005 reviews)
Everything was fine, I have nothing to complain about

Reviewed on Jul 6, 2026

Baraboo RV Resort

Baraboo RV Resort

2 out of 5
Price was CA $1,086, price is now CA $1,000 per person
CA $1,000
per person
Aug 18 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
10/10 Exceptional! (7 reviews)
Showers and bathrooms could have been a little cleaner.

Reviewed on Jul 5, 2026

Ready to book your vacation to Fennimore?

 

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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 $154 per night from Jul 9 to Jul 10
CA $154
CA $162 total
Jul 9 - Jul 10
includes taxes & fees
9.4/10 Exceptional! (85 reviews)
"Room was clean, staff was friendly, plenty of parking and air conditioning was 🙂 👍"

Reviewed on May 17, 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 Jul 12 to Jul 13
CA $88
CA $96 total
Jul 12 - Jul 13
includes taxes & fees
Napps Motel
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Fennimore WI
The price is CA $136 per night from Jul 13 to Jul 14
CA $136
CA $204 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (3 reviews)
"This 3 bedroom apartment was wonderful - we will definitely consider again the next time we are in town. The apartment was VERY clean - spotless. Bedding was fresh and clean. Beds were all comfortable. Pillows appeared to be new and comfortable. All the necessary amenities were provided including ..."

Reviewed on May 26, 2026

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
See all 121 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 Railroad Historical Society Museum

8.6/10 (4 reviews)
You can spend time browsing the exhibits at Fennimore Railroad Historical Society Museum during your trip to Fennimore. Experience the area's live music and entertainment venues.
See properties

Frequently asked questions

How much does a Fennimore vacation package cost?
You'll find cheap prices from CA $958 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.

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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.