Dickeyville Vacations from $362

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Your Dickeyville Vacation

With one of our vacation packages to Dickeyville, you'll discover infinite opportunities for relaxation and adventure. There's loads to enjoy, including its rich history and spectacular views. Dickeyville Grotto is one of the big-ticket attractions to check off your to-do list during a trip to Dickeyville. Don't put off exploring this destination any longer. Your perfect Dickeyville vacation is only a few clicks away with Expedia.

The Latest Dickeyville vacation packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Dubuque

Baymont by Wyndham Dubuque

2.5 out of 5
Price was $394, price is now $362 per person
$362
per person
Nov 22 - Nov 25
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
6.4/10 (1,008 reviews)
Breakfast was without a protein option.

Reviewed on Oct 11, 2025

Cobblestone Inn & Suites – Manchester

Cobblestone Inn & Suites – Manchester

3.5 out of 5
Price was $454, price is now $397 per person
$397
per person
Nov 22 - Nov 25
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9/10 Wonderful! (306 reviews)
The hotel was easy to find off and on. Room was clean and staff were friendly.

Reviewed on Oct 22, 2025

Hotel Julien Dubuque

Hotel Julien Dubuque

3.5 out of 5
Downtown Dubuque
Price was $523, price is now $464 per person
$464
per person
Nov 22 - Nov 25
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9.2/10 Wonderful! (1,650 reviews)
No window in our room? Is that even legal?

Reviewed on Oct 22, 2025

Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
Price was $489, price is now $434 per person
$434
per person
Nov 22 - Nov 25
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
8.4/10 Very Good! (1,012 reviews)
We had a nice stay for the weekend with friends. The property could use a refresh with some updating. The outdoor patio area with views were beautiful.

Reviewed on Oct 22, 2025

Hotel Galena

Hotel Galena

2 out of 5
Price was $583, price is now $543 per person
$543
per person
Nov 22 - Nov 25
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9.6/10 Exceptional! (216 reviews)
Very personable and attentive. The hotel was clean and updated. We really enjoyed our stay there and will be staying again.

Reviewed on Oct 14, 2025

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Discover the most popular places to visit in Dickeyville

Dickeyville Grotto

You can find out about the history of Dickeyville with a trip to Dickeyville Grotto. Stroll along the riverfront in this family-friendly area, or check out its lively bars.

Dickeyville Grotto

Dickeyville Hotel Deals

The Wisconsin Wood Inn

The Wisconsin Wood Inn

2 out of 5
224 S Main St, Dickeyville, WI
6.4/10 (213 reviews)
Javier was really helpful for our unplanned late check in. This is a no-frills clean, safe place to sleep (the bed was actually one of the better ones I've found and I've traveled alot). The furniture is not hotel-standard-generic, the carpet is clean but not new, the tables, counters and wall decorations ...

Reviewed on Oct 13, 2025

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The Wisconsin Wood Inn
Tri-States Wood Inn

Tri-States Wood Inn

2.5 out of 5
203 S Main St, Dickeyville, WI
Fully refundableReserve now, pay when you stay
$48 nightly
The price is $51 total per night from Nov 12 to Nov 13
$51 total
Nov 12 - Nov 13
Total with taxes and fees
6.6/10 (68 reviews)
I didn’t know that there were rooms on both sides of the Main Street. The staff was not very specific about where the room was and I could not find it at first because I didn’t realize I had to cross the street to find my room . Staff was very friendly but weak with English.

Reviewed on Oct 19, 2025

Tri-States Wood Inn
Grand Harbor Resort and Waterpark

Grand Harbor Resort and Waterpark

3.5 out of 5
350 Bell St, Dubuque, IA
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $115 total per night from Oct 30 to Oct 31
$115 total
Oct 30 - Oct 31
Total with taxes and fees
7.8/10 Good! (1,035 reviews)
Yes

Reviewed on Oct 18, 2025

Grand Harbor Resort and Waterpark
See all 312 properties in Dickeyville
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 Dickeyville Vacation Packages

Dickeyville Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Whispering Bluffs Winery, University of Wisconsin-Platteville and Dickeyville Grotto

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Frequently asked questions

How much does a Dickeyville vacation package cost?
You can snap up a vacation package to this top destination from $362 on Expedia. But how much your vacation to Dickeyville costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Dickeyville?
You can generally find reduced prices and better availability in November, December and January. Explore our cheap Dickeyville vacation packages and you could land some great off-season discounts.
How many days is enough for Dickeyville?
The ideal duration for your Dickeyville vacation depends on what you'd like to see. Usually, a few days to a week will give you time to check out all the leading sights and discover some hidden spots along the way.
How to find the best Dickeyville package deals?
Landing a cheap Dickeyville package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Dickeyville package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Dickeyville vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Dickeyville vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Dickeyville?
If you're planning a spur-of-the-moment Dickeyville getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Dickeyville vacation packages?
If you're like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Dickeyville vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.