Fennimore Vacations from $386

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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.
Valued Stay Sun Prairie

Valued Stay Sun Prairie

2.5 out of 5
Price was $441, price is now $386 per person
$386
per person
Apr 23 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
7/10 Good! (542 reviews)
Parking was safe and easy parking.we got a king size bed

Reviewed on Dec 29, 2025

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Save 100% on your flight
Price was $842, price is now $642 per person
$642
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9/10 Wonderful! (1,002 reviews)
Clean and staff were great!

Reviewed on Feb 19, 2026

Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
Downtown Madison
Save 100% on your flight
Price was $645, price is now $500 per person
$500
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.6/10 Exceptional! (1,002 reviews)
Very nice hotel and in walking distance for a lot of things.

Reviewed on Mar 2, 2026

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $852, price is now $677 per person
$677
per person
Apr 23 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
8.6/10 Excellent! (1,003 reviews)
Great friendly staff, clean room.

Reviewed on Feb 27, 2026

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 $628, price is now $502 per person
$502
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Madison (MSN)
9.4/10 Exceptional! (3,519 reviews)
Governor’s club worth it - privacy

Reviewed on Mar 4, 2026

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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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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
$118 nightly
The price is $124 total per night from Mar 8 to Mar 9
$124 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (78 reviews)
Room was clean, property was unique with lots of history, bed was comfortable, tub was nice

Reviewed on Feb 16, 2026

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 Mar 9 to Mar 10
$75 total
Mar 9 - Mar 10
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 $386 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.