Fennimore Vacations from $428

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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.
Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $551, price is now $428 per person
$428
per person
Jan 14 - Jan 17
found 17 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Madison (MSN)
8.6/10 Excellent! (1,004 reviews)
Location was very convenient and close to downtown restaurants. Room was very clean and amenities provided were perfect for our four night stay. Will definitely come back when I return to Madison.

Reviewed on Dec 1, 2025

Comfort Inn & Suites Madison East Interstate I-90

Comfort Inn & Suites Madison East Interstate I-90

2.5 out of 5
Price was $642, price is now $518 per person
$518
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Madison (MSN)
8.8/10 Excellent! (580 reviews)
Fresh remodel- nice, clean and comfortable bed-

Reviewed on Nov 27, 2025

Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $620, price is now $505 per person
$505
per person
Jan 14 - Jan 17
found 17 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Madison (MSN)
9/10 Wonderful! (524 reviews)
Great location along the lake and trails

Reviewed on Aug 10, 2025

Country Inn & Suites by Radisson, Madison, WI

Country Inn & Suites by Radisson, Madison, WI

3 out of 5
Monona
Price was $584, price is now $478 per person
$478
per person
Jan 14 - Jan 18
found 17 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Madison (MSN)
8.6/10 Excellent! (1,001 reviews)
We had a great stay! This hotel is perfectly located, right off the belt line. The lobby is warm and inviting, check-in was quick and easy, rooms are very clean, beds are comfy, rooms are well laid-out with a microwave, mini-fridge, coffee pot and extra pillows and blankets. The entire staff was super helpful, accommodating and friendly (shout-out to Douglas at the front desk—he was just GREAT!) We will definitely be back, thanks for a wonderful stay

Reviewed on Dec 1, 2025

Sleep Inn & Suites Madison - Monona

Sleep Inn & Suites Madison - Monona

2.5 out of 5
Price was $661, price is now $546 per person
$546
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Madison (MSN)
9.2/10 Wonderful! (1,003 reviews)
Everything was super!! Staff was very nice, friendly and helpful, the room was very clean, updated and comfortable, the included breakfast was super and the location was perfect for us!

Reviewed on Nov 13, 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

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

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 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
$95 nightly
The price is $100 total per night from Dec 8 to Dec 9
$100 total
Dec 8 - Dec 9
Total with taxes and fees
9.2/10 Wonderful! (74 reviews)
Clean room. Friendly staff.

Reviewed on Nov 16, 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 Dec 8 to Dec 9
$75 total
Dec 8 - Dec 9
Total with taxes and fees
7.2/10 Good! (34 reviews)
Clean room but tiny. 4 cup coffee maker with individual cup packs of coffee.

Reviewed on Oct 19, 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 WI
10/10 Exceptional! (109 reviews)
We've been here multiple times, and this stay won't be our last. We can always count on a well-stocked kitchen and more than comfortable accomodations. The whole family enjoys the pool table and other games and of course the great lovely country setting. Thanks again so much.

Reviewed on Nov 3, 2025

Get rates
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
See all 112 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 $428 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.