Fennimore Vacations from $624

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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.
Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $743, price is now $624 per person
$624
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (568 reviews)
We were just there for a Saturday night and enjoyed our stay. After a busy day, we enjoyed a few cocktails at the bar and the server was engaging (while busy) Bobcats off to her. A++ stay, thank you!

Reviewed on Jun 15, 2026

1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $1,019, price is now $815 per person
$815
per person
Aug 9 - Aug 14
found 15 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Madison (MSN)
9.6/10 Exceptional! (13 reviews)
Simply the BEST stay! Tony and Beth are the kindest hosts! The space is cozy and intimate; perfect for special occasions. My husband and I have had the privilege of staying here 3 times, and this will always be one of our favorite spots for a getaway! We highly recommend this gem!

Reviewed on Mar 22, 2026

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $997, price is now $809 per person
$809
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9.2/10 Wonderful! (1,000 reviews)
Did not know about a fee for parking until time of checkout.

Reviewed on Jun 22, 2026

Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

3 out of 5
Price was $773, price is now $640 per person
$640
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
9/10 Wonderful! (150 reviews)
The room was fine. Our issue was we were there 5 days and housekeeping did not come in one time to clean our room. We took our trash out ourselves. We had kids so lot of trash. I had to go get towels from front desk and put my used ones in the hallway. We had girls. We ran out of shampoo and toilets paper. Again we had girls. They swam every day. I ask why our room was not clean and the desk clerk said he had no idea….. This was an expensive week due to the USTA national trampoline and tumble event. I did see housekeeping doing other rooms but it was when weree leaving for the event.

Reviewed on Jun 23, 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 $1,091, price is now $909 per person
$909
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
9.4/10 Exceptional! (3,888 reviews)
Great location in Madison.

Reviewed on Jun 24, 2026

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Stay near popular Fennimore attractions

Fennimore Railroad Historical Society Museum

8.6/5 (4 reviews)
Step back in time at this museum showcasing the narrow gauge "Dinky" train that ran from 1878-1926. Take a ride on the operational miniature train, a weekend highlight for families.
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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
$114 nightly
The price is $121 total per night from Jul 3 to Jul 4
$121 total
Jul 3 - Jul 4
Total with taxes and fees
9.4/10 Exceptional! (85 reviews)
"Room was clean, staff was friendly, plenty of parking and air conditioning was 🙂 👍"

Reviewed on May 17, 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 Jun 28 to Jun 29
$75 total
Jun 28 - Jun 29
Total with taxes and fees
7.2/10 Good! (41 reviews)
"Woke up with bug bites on my body and there was visible dog hair on the carpet. I didn't expect much more then a clean room and a bed. I wont stay there again"

Reviewed on Jun 14, 2026

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! (114 reviews)
"No complaints. Great stay."

Reviewed on May 25, 2026

Get rates
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
See all 122 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 $624 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.