Fennimore Vacations from $349

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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.
All Star Inn & Suites

All Star Inn & Suites

2 out of 5
Price was $410, price is now $349 per person
$349
per person
Jun 2 - Jun 6
found 9 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9/10 Wonderful! (739 reviews)
Impeccably clean. Maintained with staff who are always ready to help

Reviewed on Oct 26, 2025

Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $722, price is now $501 per person
$501
per person
Jun 2 - Jun 6
found 9 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9.2/10 Wonderful! (100 reviews)
Kitchen was stocked with pots, pans, silverware, plates, bowls, dishwasher, paper towels, rags, garbage can and bags. Parking was easy there is an overflow lot for extra cars. Room was clean and presentable no complaints, staff was decent. I did however add my extra guest as a person to check in for me through Expedia since they were arriving by before me and they told them their name wasn’t on the reservation when they arrived and could not check in for us so that was my only quarrel.

Reviewed on Mar 17, 2026

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

3 out of 5
Price was $769, price is now $556 per person
$556
per person
Jun 2 - Jun 6
found 9 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
8.2/10 Very Good! (132 reviews)
If looking for a peaceful place to get away this is yhe place.Is close to the dells and all the restaurant also walmart.

Reviewed on Mar 26, 2026

Dells Park Motel

Dells Park Motel

2 out of 5
Downtown Wisconsin Dells
Price was $538, price is now $454 per person
$454
per person
Jun 2 - Jun 6
found 9 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
7.6/10 Good! (95 reviews)
Very basic old school motel. Very 80’s but clean. No issues with the stay. If you’re looking for Great Wolf amenities, or even a modern motel, look elsewhere. That said, if you come to the Dells to enjoy the activities and only use the room to sleep, it’s a budget friendly choice

Reviewed on Jul 25, 2024

Amber's Inn & Suites

Amber's Inn & Suites

2 out of 5
Downtown Wisconsin Dells
Price was $446, price is now $388 per person
$388
per person
Jun 2 - Jun 6
found 9 hours ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9.4/10 Exceptional! (1,001 reviews)
Everything was great but no coffee at 7am, they were closed overnight. Hot tub was nice but you have to walk outside and thru office to get there.

Reviewed on Mar 28, 2026

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Discover the most popular places to visit in Fennimore

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
$106 nightly
The price is $112 total per night from Apr 2 to Apr 3
$112 total
Apr 2 - Apr 3
Total with taxes and fees
9.4/10 Exceptional! (81 reviews)
The doors were unlocked with everything cleaned and ready for guests. Once we closed our room door we unlocked it with the last 4 digits of our phone number. We never saw staff but we were well taken care of and enjoyed the ease of coming and going

Reviewed on Mar 27, 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 Apr 5 to Apr 6
$75 total
Apr 5 - Apr 6
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 118 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 $349 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.