Fennimore Vacations from $173

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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.
Motel 6 Janesville, WI

Motel 6 Janesville, WI

2 out of 5
Price was $213, price is now $173 per person
$173
per person
Dec 8 - Dec 11
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
7/10 Good! (808 reviews)
Unsightly people. Drunk loud . Would not recommend it for even one night.

Reviewed on Oct 20, 2025

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $570, price is now $468 per person
$468
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
8.6/10 Excellent! (1,009 reviews)
Beautiful hotel, right on the lake and downtown Madison, near great restaurants!

Reviewed on Oct 12, 2025

Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

2.5 out of 5
Leopold
Price was $453, price is now $389 per person
$389
per person
Jan 16 - Jan 18
just found
Roundtrip non-stop flight included
Tampa (TPA) to Madison (MSN)
7.2/10 Good! (1,510 reviews)
the 2 king bed option was perfect, the bath room was alitttle small but everything else was fine need additional places to plug devices into that are not connected to the wall switch.

Reviewed on Oct 16, 2025

The Wisconsin Hotel & Conference Center

The Wisconsin Hotel & Conference Center

2.5 out of 5
Price was $724, price is now $633 per person
$633
per person
Nov 27 - Dec 1
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Madison (MSN)
9.4/10 Exceptional! (103 reviews)
We were given wrong room number and tried to get in at 11:15 pm. I felt terrible for family we woke up. The water never really got hot in shower- just luke warm. They have a few things they need to work out before bar and restaurant actually open.

Reviewed on Oct 19, 2025

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $645, price is now $566 per person
$566
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
9.2/10 Wonderful! (1,005 reviews)
Super friendly staff. Very high quality facilities. Fabulous view of the lake from my room and around the property.

Reviewed on Oct 20, 2025

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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

4.5/5(26 reviews)

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

4/5(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.

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
$110 nightly
The price is $116 total per night from Nov 2 to Nov 3
$116 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (73 reviews)
"Very cool old downtown hotel"

Reviewed on Oct 18, 2025

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
$71 nightly
The price is $75 total per night from Oct 22 to Oct 23
$75 total
Oct 22 - Oct 23
Total with taxes and fees
7.2/10 Good! (28 reviews)
"For the price it was a good place to lay down and sleep."

Reviewed on Sep 28, 2025

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
10/10 Exceptional! (108 reviews)
"Morning coffee on the deck was amazing with water run and sound of nature. The kids and husband loved playing with pool table and foosball. Kitchen had everything we needed. Loved having the garage space for dog kennels. Our dogs enjoyed the outside space too run and play. Plenty of seating areas ..."

Reviewed on Sep 29, 2025

Get rates
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
See all 118 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 $173 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.