Fennimore Vacations from $705
Book a Hotel + Flight or Car together to unlock savings
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.
AmericInn by Wyndham Madison South
Monona
$719
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (1,007 reviews)
Very friendly and helpful staff. Clean rooms and property. Basic amenities. Heard the food was good but didn't eat there.
Reviewed on Oct 13, 2026
Stay near popular Fennimore attractions
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 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 Hotel Deals
Fenway House Hotel
1096 Lincoln Ave Fennimore WI
$106 nightly
$112 total
Oct 18 - Oct 19
Total with taxes and fees
9.2/10 Wonderful! (105 reviews)
"Good for what it was."
Reviewed on Oct 12, 2026
Napps Motel
645 12TH ST HWY 18 EAST Fennimore WI
Fully refundableReserve now, pay when you stay
$71 nightly
$75 total
Oct 15 - Oct 16
Total with taxes and fees
7/10 Good! (50 reviews)
"They don't have a morning breakfast no pop machine"
Reviewed on Oct 12, 2026
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
Fennimore WI
10/10 Exceptional! (119 reviews)
"Very nice stay!"
Reviewed on Sep 29, 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 $705 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.