Fennimore Vacations from $326

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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.
Super 8 by Wyndham Madison South

Super 8 by Wyndham Madison South

2.5 out of 5
Price was $380, price is now $326 per person
$326
per person
Oct 30 - Nov 2
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
7/10 Good! (1,003 reviews)
Friendly staff, clean. Decorations outdated

Reviewed on Aug 28, 2025

Bluegreen Christmas Mountain Village, an Ascend Resort

Bluegreen Christmas Mountain Village, an Ascend Resort

3 out of 5
Price was $758, price is now $635 per person
$635
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
8.4/10 Very Good! (118 reviews)
We had stayed in this property before, and again this trip did not disappoint!

Reviewed on Jul 22, 2025

Bluegreen Odyssey Dells

Bluegreen Odyssey Dells

3.5 out of 5
Price was $726, price is now $619 per person
$619
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
9.4/10 Exceptional! (150 reviews)
Great accommodations for a family vacation. Large rooms that have two bedrooms, living area and a small kitchen area with a full size refrigerator. There is almost no need to go out to eat as kitchen is stocked with most cookware. It is within walking distance to the water park and easy to come and go between the two.

Reviewed on Aug 25, 2025

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $1,125, price is now $980 per person
$980
per person
Oct 6 - Oct 10
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
9.2/10 Wonderful! (1,005 reviews)
Just loved the lake view from our room

Reviewed on Sep 2, 2025

1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $539, price is now $477 per person
$477
per person
Nov 21 - Nov 23
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
9.6/10 Exceptional! (11 reviews)
The hosts were gracious and thorough with amenities. The property was lovely and comfortable. The food was delicious.

Reviewed on Jul 11, 2024

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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

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

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 Sep 7 to Sep 8
$124 total
Sep 7 - Sep 8
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
$71 nightly
The price is $75 total per night from Sep 4 to Sep 5
$75 total
Sep 4 - Sep 5
Total with taxes and fees
Napps Motel
Quaint & Quiet 2 bed 1 bath

Quaint & Quiet 2 bed 1 bath

Fennimore
$145 nightly
The price is $153 total per night from Sep 4 to Sep 5
$153 total
Sep 4 - Sep 5
Total with taxes and fees
Quaint & Quiet 2 bed 1 bath
See all 119 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.

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Frequently asked questions

How much does a Fennimore vacation package cost?
You'll find cheap prices from $326 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.