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11 romantic getaways in southern Illinois

If you’re looking to spend a romantic getaway in southern Illinois, you’ve come to the right place.

Southern Illinois is known for its beautiful nature scenes, entertaining activities, and incredible wineries.

Read on to discover some of the best places to go with your special someone for a weekend retreat in southern Illinois.

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Blue Sky winery is a perfect destination for a romantic getaway in southern Illinois.
Blue Sky Winery (Photo credits: Blue Sky Winery)

Spend a romantic weekend getaway in Illinois at the Blue Sky Vineyard

  • Address: 3150 S Rocky Comfort Road, Makanda, IL 62958
  • Highlights: Romantic Tuscan-inspired winery and bed and breakfast

Enjoy breathtaking views of the Shawnee National Forest while you sip your wine in style at this Tuscan-inspired retreat.

Wondering where to stay in Shawnee National Forest? Check out these amazing cabins in and around Shawnee National Forest. 

Spend your couple’s retreat in Illinois the right way, by basking in the luxurious comfort of one of their on-site suites.

Wake up to the gorgeous ambiance of the winery and enjoy their traditional Portuguese breakfast, included with your stay. The café serves up appetizers, deli sandwiches, and fresh pizza daily.

Here is an overview of more couples resorts in Illinois or take a look at these cool hotels in Illinois.

Pouring wine in a glass during dinner
Enjoy a wine tasting tour

Experience the Shawnee Hills Wine Tour

  • Address: 2865 Hickory Ridge Road, Pomona, IL 62975
  • Highlights: Taste the flavors of the local vineyards with this shuttle bus tour of Shawnee Hills wineries

When it comes to romantic weekend getaways in southern Illinois, it doesn’t get any better than exploring the countryside with the one you love.

This shuttle bus wine tour will take you on a journey through the beautiful landscapes, charming small towns, and rich history that surround the best wineries in southern Illinois.

Featuring live music events year-round, this is a trip that is sure to keep you entertained all weekend long.

Take part in their passport program for exclusive deals and discounts at all the local wineries of Shawnee Hills Wine Trail.

Burden falls are one of the best waterfalls in Illinois
Beautiful Burden Falls in Shawnee National Forest

Explore Shawnee National Forest

  • Address: Herod, IL 62946
  • Highlights: Shawnee National Forest features plenty of outdoor activities for couples to enjoy such as horseback tours, hiking trails, fishing, camping, birdwatching, and rock climbing.

For an inexpensive weekend getaway in Illinois, you will want to check out Shawnee National Forest.

The lush greenery and rolling hills make this one of the most exquisite destinations in southern Illinois.

No matter what season you’re visiting in, the Shawnee National Forest will impress you with over 280,000 acres of unique ecosystems including streams, waterfalls, ponds, prairies, and more.

You and your partner can hike the trails on your own or participate in guided horseback tours with Giant City Stables. If you love hiking, check out the Pomona natural bridge trail.

There is plenty to see and enjoy at Shawnee National Forest.

If you love hiking, check out this list of epic state parks in southern Illinois.

Unique places to stay for a weekend getaway in southern Illinois

The Green Tree Inn

  • Address: 15 Mill Street, Elsah, IL 62028
  • Highlights: At the Green Tree Inn, you can enjoy a weekend retreat that features exciting activities, romantic accommodations, and exquisite views of Elsah, Illinois.
Romantic B&B in Southern Illinois

Nestled within the top-rated scenic town in Illinois, The Green Tree Inn is the perfect destination for a romantic weekend retreat in southern Illinois.

For the ultimate romantic experience, order their special occasion package which includes a fresh bouquet as well as a gift card to one of the most intimate dining experiences in the village of Elsah.

While you’re visiting, you’re going to want to experience all the local activities and attractions, such as bird watching, hiking, horseback riding, and even ziplining through the forest.

You and your sweetheart can also take a ride along the Mississippi on the multi-level, 49-passenger tour boat, The Hakuna Matata.

Check prices and availability:


Beall Mansion

  • Address: 407 East 12th Street, Alton, IL 62002
  • Highlights: Beall Mansion is one of the most elegant bed and breakfast boutique hotel experiences that you will find in southern Illinois. It features classic, luxury accommodations, and excellent service.

If you’re looking for a luxury experience at an affordable price, look no further than the Beall Mansion for your next romantic weekend getaway in southern Illinois.

This historic mansion was constructed in 1903. Since then, it has been fully restored to a hotel and museum, exquisitely encapsulating all of its original glory.

The Beall Mansion features a lavish experience that is truly one-of-a-kind.

Each stay includes access to a 24-hour all-you-can-eat chocolate buffet as well as complimentary breakfast daily and 24-hour hot beverage service.

Select a room with a whirlpool tub and a fireplace to set the mood for the perfect romantic getaway with the one you love.

Check prices and availability:


Davie School Inn

  • Address: 300 Freeman Street, Anna, IL 62906
  • Highlights: The Davie School Inn is a historic hotel that was exquisitely renovated from an old schoolhouse. It is conveniently nestled along the Shawnee Hills Wine Trail.

This unique bed and breakfast was converted from a schoolhouse.

Featuring eight unique, classroom-themed rooms, and three luxury suites, this is an ideal location for a couple’s retreat in southern Illinois.

Each room includes a kitchenette stocked with coffee and tea as well as a deluxe jacuzzi bathtub.

For the ultimate experience, indulge in their romance package which includes breakfast brought straight to your room each morning.

The Davie School Inn is conveniently located in Anna, IL just a few minutes away from the Shawnee National Forest and the Shawnee Hills Wine Trail.

If you are looking to have an outdoor lunch or dinner at one of the local attractions, they will lend you a fully outfitted picnic basket and blanket for the occasion.

They even have bikes available to borrow if you would like to explore the nearby area while enjoying the sunshine.

Inn at 835

  • Address: 835 South 2nd Street, Springfield, IL 62704
  • Highlights: The Inn at 835 is a boutique hotel with timeless luxury accommodations featuring antique furniture and décor.

Enjoy an opulent setting in a peaceful environment when you book your stay at the timelessly decorated Inn at 835 Boutique Hotel.

With its luxurious accommodations and vintage decor, this is one of the most beautiful destinations for a romantic getaway in southern Illinois.

Every day during your stay, you and your loved one can indulge in a complimentary glass of wine while relaxing in their exquisite guest sitting room.

Each unique room comes equipped with antique furnishings, hand-milled French soaps, free wi-fi, and much more.

During your stay, you and your partner can tour the historic town and Illinois state capital of Springfield, including many of the Abraham Lincoln historical sites which are located nearby.

Rent a romantic cabin with a hot tub

Cozy up to the one you love in a charming cabin with a hot tub.

No matter where you’re visiting, renting a cabin is certainly one of the most romantic weekend getaways that you will find.

The relaxing and intimate environment cannot be matched by any other vacation experience.

Better yet, there are plenty of romantic cabins available for rent in southern Illinois. Didn’t find what you were looking for? Check out our list of cabins in southern Il.

Top destinations for a romantic retreat in southern Illinois

Makanda boardwalk
The Makanda boardwalk with all kinds of quaint shops (photo credits: Paul Sableman)


  • Highlights: Explore the serene scenes of nature on display and visit quaint shops and eateries in Makanda, Illinois.

Known throughout southern Illinois as the gateway to the Shawnee National Forest, Makanda has all sorts of indoor and outdoor activities for you and your partner to enjoy on your weekend getaway in Illinois.

Visit the Makanda boardwalk, home to many of the downtown attractions in the area, including the Makanda Trading Company which features gifts and art sourced from various locations all over the world.

Another location to check out is the Makanda Country store which specializes in gourmet coffee, sandwiches, and delectable hand-scooped ice cream.

There are also plenty of artisan jewelry shops such as Allan Stuck’s world-renowned art and jewel studio so you can find a gift or two to commemorate your trip.

Another fun way to experience all Makanda has to offer is by zip-lining through 83 acres of the Shawnee National Forest on their brand-new zip line tour.

Other local activities include horseback riding, hiking, camping, and visiting the gorgeous wineries nearby.

The Oyster bar at Grafton Harbor
The Oyster bar at Grafton Harbor (photo credits: Great Rivers & Roads)


  • Highlights: Grafton is a beautiful small town along the Mississippi and Illinois rivers where you can explore nature, visit local wineries and eateries, and take part in exciting and unique activities.

Located just down the road from Elsah, Grafton is a small town in southern Illinois that stands out for its exquisite nature scenes, lush wineries, and its prime location along the Mississippi River.

There is no shortage of things to do in Grafton, Illinois.

Check out the local wineries and eateries, where they serve locally sourced blends, each inspired by their unique histories.

Cruise along the Grafton Harbor in style on the Grafton Harbor Floating Winery where you can experience unique flavors while you take in the beautiful river scenes.

On the weekends, you can frequently hear live music playing at many of the local venues such as the Grafton Loading Dock.

Riding the scenic aerial lift is a must-try activity while you are visiting Grafton. Here, you will experience an exclusive aerial view of the Mississippi and Illinois rivers that you will never forget.

Another exciting thing to do in Grafton is to explore Pere Marquette State Park which displays breathtaking natural stone formations that date back millions of years.

There are plenty of hiking trails to discover in addition to a plethora of fishing spots and rock-climbing destinations.

Since admission is free, this is the perfect activity to add to your schedule for an inexpensive romantic getaway in Illinois.

Lincoln theatre in Belleville, Illinois
The Lincoln Theatre in Belleville (photo credits: Daniel X. O’Neill)


  • Highlights: Belleville is a historic and lively town with a bustling downtown area. You can enjoy a variety of activities such as catching a movie in their local historic theaters, enjoying a bite to eat, or shopping in one of their many boutiques.

In the town of Belleville, Illinois you can experience the vivacious downtown scenes that are lined with elegant brick buildings.

In this historic district, you will find jewelers, collectible shops, florists, bakeries, and fashion boutiques.

There are also plenty of diverse restaurants to choose from including sushi, Chinese, Mexican, pizza, and even cheeseburger joints.

Located just 15 minutes away from St. Louis, Missouri, this is one of the busiest cities in southern Illinois.

Spend an afternoon exploring the historic Lincoln Theatre, which has been entertaining visitors and locals since it opened in 1921.

Another nearby entertainment option is the exciting Skyview drive-in theater, the only drive-in movie theater that remains in the St.Louis area.

Here, you can enjoy a romantic evening by catching a movie showing on their 115-foot movie screen from April to November.

For history lovers, the Scott field heritage airpark is a must-see attraction. Located on the outskirts of Belleville, this Air Force base is one of the oldest operating facilities in the United States.

You can explore the historic aircraft that were flown by the US Air Force dating back to World War 1.

There is no shortage of local markets in downtown Belleville. A seasonal farmer’s market graces the area every Saturday morning from May to October.

Here, you can find everything from fresh market produce to handmade arts and crafts.

Visit during the winter months to experience the German-style Christmas market known as Christkindlmarket which lights up the downtown Public Square from November to late December.

You can even find classic German treats and gifts to purchase for the one you love.

Here is an overview of more fun things to do in Illinois during winter.


When it comes to romantic getaways, southern Illinois has plenty of places for you to enjoy with the one you love.

Whether you plan to spend your romantic retreat experiencing the flavors of the countless wineries or exploring the serenity of the exquisite nature scenes on display in one of their many state parks, there is something for everyone to enjoy in southern Illinois.

Here is an overview of more southern Illinois attractions.