Fennimore Vacations from $316

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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.
Baymont by Wyndham Whitewater

Baymont by Wyndham Whitewater

2.5 out of 5
Price was $380, price is now $316 per person
$316
per person
Sep 14 - Sep 19
found 2 hours ago
Roundtrip flight included
Minneapolis (MSP) to Madison (MSN)
7.4/10 Good! (767 reviews)

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $1,408, price is now $1,083 per person
$1,083
per person
Oct 2 - Oct 4
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (1,002 reviews)

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $1,306, price is now $1,087 per person
$1,087
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
9.2/10 Wonderful! (1,001 reviews)
Great hotel. I highly recommend it.

Reviewed on Jul 21, 2026

Hilton Garden Inn Madison West/Middleton

Hilton Garden Inn Madison West/Middleton

3 out of 5
Price was $750, price is now $630 per person
$630
per person
Oct 2 - Oct 4
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
8.8/10 Excellent! (1,000 reviews)

The Speckled Hen Inn B&B

The Speckled Hen Inn B&B

4 out of 5
Price was $812, price is now $687 per person
$687
per person
Oct 2 - Oct 4
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
9.8/10 Exceptional! (9 reviews)
Beautiful, quiet, spacious property close to Madison.

Reviewed on Oct 17, 2022

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Stay near popular Fennimore attractions

Fennimore Doll and Toy Museum

8.0/10 (7 reviews)
Step back in time at this charming museum showcasing dolls and toys from the 1800s through 2000s. Explore over 80 display cases of nostalgic treasures, from bisque dolls to cast iron cars.
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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
$122 nightly
The price is $129 total per night from Jul 23 to Jul 24
$129 total
Jul 23 - Jul 24
Total with taxes and fees
9.4/10 Exceptional! (87 reviews)
"If you want a quiet clean room, then this is the place for rest and relaxation. We will stay here again the next time we are in town."

Reviewed on Jul 21, 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 Jul 23 to Jul 24
$75 total
Jul 23 - Jul 24
Total with taxes and fees
7.2/10 Good! (44 reviews)
"We last-minute booked this motel during our roadtrip and it was great. The front desk was closed but we called the number on the door and they picked up and got us into our room without any issues. Room checked all of our boxes"

Reviewed on Jul 10, 2026

Napps Motel
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Fennimore WI
$166 nightly
The price is $175 total per night from Jul 23 to Jul 24
$175 total
Jul 23 - Jul 24
Total with taxes and fees
9/10 Wonderful! (4 reviews)
"The property was exactly as described. The decor was super cute and the beds were very comfortable! Highly recommend this property!"

Reviewed on Jul 11, 2026

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
See all 116 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 $316 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.