Fennimore Vacations from $341

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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.
Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $406, price is now $341 per person
$341
per person
Apr 17 - Apr 19
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9.2/10 Wonderful! (100 reviews)
We got in late and it was hard to find our villa, staff were not very accommodating to help us find it.

Reviewed on Mar 14, 2026

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $1,568, price is now $1,271 per person
$1,271
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Madison (MSN)
9/10 Wonderful! (1,000 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 It seems very outdated.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

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $2,205, price is now $1,834 per person
$1,834
per person
May 7 - May 11
found 9 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
8.6/10 Excellent! (1,003 reviews)
Great friendly staff, clean room.

Reviewed on Feb 27, 2026

Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
Price was $1,068, price is now $894 per person
$894
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Madison (MSN)
9/10 Wonderful! (1,015 reviews)
It is a beautiful place , My only complaint would be that the pool area is very loud when the kid splash area is on So not relaxing in the hottub

Reviewed on Mar 13, 2026

Comfort Suites Madison West - Middleton

Comfort Suites Madison West - Middleton

2.5 out of 5
Junction Ridge
Price was $1,073, price is now $917 per person
$917
per person
May 7 - May 11
found 9 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
8/10 Very Good! (478 reviews)
Staff was great. Rooms nice and spacious! Good location.

Reviewed on Mar 7, 2026

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Discover the most popular places to visit in Fennimore

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

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

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 Apr 12 to Apr 13
$112 total
Apr 12 - Apr 13
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
$68 nightly
The price is $71 total per night from Mar 17 to Mar 18
$71 total
Mar 17 - Mar 18
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 117 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 $341 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.