Anna Holidays

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    Find the right fit

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Your Anna Holiday

From its rural countryside to its welcoming locals and beyond, there's loads to love about Anna. Discover the delights of this awesome city with an Anna holiday package that's made for you. Every trip to Anna needs a well-crafted itinerary. Fill yours with famous sights like Shawnee Community College, Lincoln Heritage Winery and Anna City Park. Your perfect Anna holiday is clicks away. Explore flights, hotels and more on Expedia for a trip that's tailored just for you.

Anna Holiday

Anna Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Williamson County Regional Airport (MWA)
Population
4,300
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Giant City State Park, Blue Sky Vineyards and StarView Vineyards

Our pick of the best Anna Hotel Deals

Hotel 7 Inn Anna
Hotel 7 Inn Anna
2.5 out of 5
100 Richview Dr, Anna, IL
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 18 July to 19 July
AU$142
18 July - 19 July
includes taxes & fees
6.4/10 (206 reviews)
"Great pool"

Reviewed on 29 Jun. 2025

Hotel 7 Inn Anna
Rest, Relax and Renew. Our log cabin experience awaits your arrival.
Rest, Relax and Renew. Our log cabin experience awaits your arrival.
Anna
The price is AU$319 per night from 20 July to 21 July
AU$319
20 July - 21 July
includes taxes & fees
9.8/10 Exceptional! (388 reviews)
Wine trail
"Quiet cozy cabin with all the amenities needed to enjoy the wine trail or Shawnee forest trails. Very clean and well appointed for a nice relaxing weekend!"

Reviewed on 7 Jul. 2025

Rest, Relax and Renew. Our log cabin experience awaits your arrival.
Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery
Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery
Cobden
9.8/10 Exceptional! (133 reviews)
"Cabin and hot tub were nice. We loved how quiet and peaceful it was. No response from owner. There is a smart tv and dvd player. Dvds were scratched or dirty, no wifi so couldn't watch tv. A few deer were seen on the property everyday."

Reviewed on 17 Jun. 2025

Get rates
Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery
See all 411 properties in Anna
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an Anna holiday package cost?
You'll find cheap prices on Expedia for your Anna getaway. However, factors like the length of stay, hotel choice and season will determine how much your holiday to Anna costs.
What are the cheapest months to go to Anna?
January, August and December are great times to search for cheap Anna holiday packages. Opting to travel in quieter periods means you'll typically find reduced prices on flights and accommodation.
How many days is enough for Anna?
With a well-organised travel plan, you can easily hit the most popular Anna attractions in a few days. But if you want to discover hidden gems or take day trips, consider booking your Anna holiday for longer.
How to find the best Anna package deals?
Start your search for an Anna package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Anna package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Anna adventure underway.
Is it cheaper to book an Anna holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalised Anna holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Anna?
If you have your Anna travel dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Anna?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to escape to Anna.
  2. Plan your budget wisely: On top of the price of your hotel, you should consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Anna.
  3. Decide how long to go away for: Now that you're more familiar with Anna, you can work out the ideal length of your holiday. Put together a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find an Anna holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.