Fennimore Vacations from $382

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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.
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 $450, price is now $382 per person
$382
per person
May 12 - May 14
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Madison (MSN)
9.4/10 Exceptional! (3,531 reviews)
This was our third stay here, and our first time not up on the governor's executive club level. Our room was very clean and comfortable with a gorgeous Capitol view. Your staff is very friendly and the location is perfect. We will be back!!

Reviewed on Mar 10, 2026

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $972, price is now $809 per person
$809
per person
Apr 23 - Apr 26
found 23 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Madison (MSN)
9/10 Wonderful! (1,002 reviews)
Meh. I had much higher hopes for this property. It seems very outdated. No access to online streaming services. We had to watch cable television with endless commercial commercials. On the plus side, the lady that checked us in and the valet guy was very friendly. I also found the valet prices to be a bit steep.

Reviewed on Mar 8, 2026

Ironworks Hotel

Ironworks Hotel

3.5 out of 5
Price was $562, price is now $474 per person
$474
per person
May 16 - May 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Madison (MSN)
9.4/10 Exceptional! (630 reviews)
Georgeous place. Fantastic. Uniq expirience.

Reviewed on Mar 4, 2026

The Saddlery Madison Downtown

The Saddlery Madison Downtown

2 out of 5
Downtown Madison
Price was $1,113, price is now $947 per person
$947
per person
Apr 10 - Apr 14
found 18 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Madison (MSN)
9.2/10 Wonderful! (80 reviews)
Clean space, easy check in.

Reviewed on Mar 8, 2026

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Discover the most popular places to visit in Fennimore

Whispering Winds Winery

You can enjoy a tasting or tour at Whispering Winds Winery during your travels to Fennimore. Discover the area's museums and shops.

Whispering Winds Winery

Carr Valley Cheese

Enjoy a stop at Carr Valley Cheese, an entertaining place to visit in Fennimore. Experience the area's live music and theater scene.

Carr Valley Cheese

Fennimore Doll and Toy Museum

You can spend time browsing the exhibits at Fennimore Doll and Toy Museum in Fennimore. Discover the area's live music and monuments.

Fennimore Doll and Toy Museum

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
$106 nightly
The price is $112 total per night from Mar 15 to Mar 16
$112 total
Mar 15 - Mar 16
Total with taxes and fees
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
$64 nightly
The price is $68 total per night from Mar 15 to Mar 16
$68 total
Mar 15 - Mar 16
Total with taxes and 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! (112 reviews)
The house was spacious, clean, and had everything we needed for our weekend stay! We loved our experience!

Reviewed on Feb 22, 2026

Get rates
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
See all 115 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.

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 $382 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.