Fennimore Vacations from $517
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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.
The Latest Fennimore vacation packages
Price found within the past 48 hours. Click for updated prices.
Club Wyndham Glacier Canyon
$537
per person
Oct 19 - Oct 22
found 7 hours ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
9/10 Wonderful! (426 reviews)
My husband and I stayed with Club Wyndham for the first time at the Wilderness Glacier Canyon Lodge. Our four night stay was nothing but pure bliss, and we definitely plan on coming back! After check-in we were told about some of the benefits Wyndham timeshares had to offer and were asked if we would like to attend their tour, but we were not interested at the time to which they had no problem with and told us to enjoy our stay!
The Wilderness resort brings back much nostalgia because I used to visit there all the time with my family as a child. Now, my husband and I want to continue the tradition with our family. This place has everything the whole family could want on a vacation. From the waterparks to the arcades to food, they have it all. We have already made so many great memories there, and we highly recommend going! Just remember they do get very busy during peak season, so if you’re looking for a more laid back version of the Wilderness, we recommend going during their off-season! Also, be sure to check out the downtown (our favorite restaurant is the Dell Bar) as well as Devil’s Lake State Park!
Reviewed on Jun 3, 2026
Dellshire Resort
$582
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9/10 Wonderful! (232 reviews)
Only negative was the pools, arcade, and gift shop (where the coffee, pastries, gelato are sold) closed at 10pm even on weekends.
Reviewed on Aug 10, 2026
Stay near popular Fennimore attractions
Fennimore Railroad Historical Society Museum
8.6/10 (4 reviews)
Step back in time at this museum showcasing the narrow gauge "Dinky" train that ran from 1878-1926. Take a ride on the operational miniature train, a weekend highlight for families.
Fennimore Doll and Toy Museum
8.0/10 (7 reviews)
Step back in time at this charming museum showcasing dolls and toys from the 1800s through 2000s. Explore over 80 display cases of nostalgic treasures, from bisque dolls to cast iron cars.
Carr Valley Cheese
9.0/10 (26 reviews)
Award-winning Wisconsin cheese traditions meet modern artisanal craftsmanship at this Fennimore destination. Sample fresh curds and aged cheddars while meeting Igor, the World Famous Giant Mouse.
Fennimore Hotel Deals
Fenway House Hotel
1096 Lincoln Ave Fennimore WI
Fully refundableReserve now, pay when you stay
$109 nightly
$115 total
Sep 10 - Sep 11
Total with taxes and fees
9.4/10 Exceptional! (88 reviews)
"Everything was great though the volume on the tv did not work, no volumn"
Reviewed on Aug 2, 2026
Napps Motel
645 12TH ST HWY 18 EAST Fennimore WI
Fully refundableReserve now, pay when you stay
$64 nightly
$67 total
Aug 13 - Aug 14
Total with taxes and fees
7/10 Good! (48 reviews)
"This is an old run-down property. The furniture in the room, well I have seen better furniture on the curb for “free”. The bathroom is about the size you would find in a motor home. The place is just creepy, it could be the “Bates Motel” from movie Psycho. Recommend someone pay more money than stay ..."
Reviewed on Aug 3, 2026
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore WI
$166 nightly
$175 total
Aug 11 - Aug 12
Total with taxes and fees
9/10 Wonderful! (4 reviews)
"The property was exactly as described. The decor was super cute and the beds were very comfortable! Highly recommend this property!"
Reviewed on Jul 11, 2026
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.
Find the Best Fennimore Vacation Packages
Fennimore Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,500 |
Max Temp Winter | 25ºF |
Max Temp Summer | 80ºF |
Top Sights | Whispering Winds Winery, Fennimore Railroad Historical Society Museum and WI River Outings |
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Frequently asked questions
How much does a Fennimore vacation package cost?
You'll find cheap prices from $517 on Expedia for your Fennimore getaway. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Fennimore costs.
What are the cheapest months to go to Fennimore?
If you'd like to book a cheap Fennimore vacation package, consider planning a trip in November, December and January. You'll typically find better prices on airfares and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Fennimore?
The ideal length of your Fennimore vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to tick off all the top sights and discover some hidden treasures along the way.
How to find the best Fennimore package deals?
Begin your search for a Fennimore package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Fennimore package deal straight 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 adventure off to a flying start.
Is it cheaper to book a Fennimore vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights individually. Better still, you can customize your Fennimore escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Fennimore?
If you're planning an impromptu Fennimore adventure, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Fennimore vacation packages?
Your Fennimore trip should be an escape from your daily routine, not a reason for money worries. So to allow you a little more flexibility, we've teamed up with online lender Affirm to offer 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 are no hidden 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.
