Vacation rentals in Anna

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Top-rated vacation rentals in Anna

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Top guest favorite

A cabin with wooden exterior is surrounded by tall trees and shaded ground. A spacious porch is visible at the front entrance. A calm dog sits on the ground in the foreground, offering a glimpse of the natural tranquility of the setting.

Cabin in Alto Pass

Ma's Cabin, Alto Pass, IL. Fine country lodging.

Cute and country remodel done in 2019. Recent new appliances, furnishings, flooring, heat & A/C, washer & dryer. Cabin is secluded and quiet plus 1/2 mile from Alto Pass Lookout Point and right in the middle of many award-winning wineries. 15 miles from Carbondale 4 miles from Giant City 30 miles from Garden of the Gods 6 lakes within 10-mile radius Hundreds of miles of hiking trails in nearby Shawnee National Forest 6 miles from Bald Knob Cross Please, no dogs! No smoking in cabin!

4.99 out of 5 average rating, 337 reviews

Superhost

Camper/RV in Cobden

Kate’s Cozy Camper

Hello and welcome! Welcome to our cozy camper. Glamp it up with us April through Mid-November! We are close to trails, vineyards, mead, and cider! We are walkable distance to Cobden, but with the seclusion of our woods and your own fire pit that leads directly to a disc-golf course. Cozy, peaceful, great affordable get away. December adventurous guests! We usually close down for winter but we are opening up for a lower rate! We will have heat and power but no water. Less glamp, more “camp.”

4.95 out of 5 average rating, 106 reviews

Top guest favorite

A modern dome structure features large glass panels creating a bright and inviting environment. Surrounded by lush greenery, the architecture harmonizes with nature. A wooden deck with seating is visible in front, offering a space for relaxation and outdoor enjoyment.

Dome in Cobden

The Dome At Blueberry Hill

Escape to The Dome at Blueberry Hill, where comfort meets nature for a truly unforgettable glamping experience. Set on two private acres along the scenic Shawnee Hills Wine Trail and minutes from the charming village of Cobden- you’ll enjoy peaceful seclusion with easy access to local charm. The fully insulated dome offers cozy, climate-controlled comfort year-round. Sip wine under the stars or unwind in style indoors. Make lasting memories at The Dome- your luxury glamping retreat awaits.

5.0 out of 5 average rating, 231 reviews

Top guest favorite

A red barn with a peaked roof is set against a lush green landscape, reflecting softly in a calm pond nearby. Tall grasses frame the water’s edge, while trees provide a natural backdrop under a partly cloudy sky.

Cabin in Dongola

Charming Cabin Overlooking 5 Acre Lake

This cozy, newly remodeled, and inviting cabin offers you a relaxing, serene, and tranquil setting. During your stay you will see nature at its finest. Enjoy a drink on the large deck overlooking the picturesque landscape as well as the lake. If you enjoy fishing then this stocked lake is the place for you. Feel free to fish on the bank or the dock. This cabin is part of the original homestead that was established in 1855 by Valentine Kimber. Located close to wine trails and interstate 57.

5.0 out of 5 average rating, 104 reviews

Top guest favorite

The exterior of a charming lodge is surrounded by trees, featuring large windows and a wraparound deck. A wooden structure showcases a combination of stone and wood elements, while a spacious pool area is visible in the bottom left corner, framed by nature.

Cabin in Goreville

Secluded and Stunning Lodge - Hot Tub, Hiking

Hi, hello there, welcome! Bring your friends and family and get ready to relax. Our spacious lodge is the perfect getaway for those looking for some peace and privacy. Located adjacent to Ferne Clyffe State Park, you can lace up your hiking boots and wander straight onto the trails. The Southern Illinois Wine Trail and multiple state parks are a short drive away, but you'll soon find yourself back in the privacy of our 28 acre retreat. Come and enjoy all that our unique cabin has to offer!

4.98 out of 5 average rating, 106 reviews

Top guest favorite

A spacious porch is lined with wooden rocking chairs, offering a view of the surrounding greenery. An interior area features a cozy seating arrangement with a patterned rug and rustic decor. Outside, an inviting fire pit area with comfortable chairs is set amidst the natural landscape.

Cabin in Anna

Shawnee Hiking!Hot tub!Fire Pit!Wine Trail!

WELCOME TO LUXURY GLAMPING ON THE SHAWNEE WINE TRAIL OF BEAUTIFUL SOUTHERN ILLINOIS. You will be resting in an authentic oak timber cabin, built on the historical "Trail of Tears" in Union County - Anna, Illinois. This lodging offers the rustic appeal, a taste of Native America with the comforts of contemporary amenities including an outdoor hot tub all year long! *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #2.

4.91 out of 5 average rating, 181 reviews

Guest favorite

A charming exterior view of a blue house is presented, featuring white trim and multiple windows. A covered porch area includes two red chairs and a black barbecue grill. Flower beds with plants are positioned along the front, set against a gravel area and surrounding greenery.

Home in Cobden

Wine trail cozy cabin! Hot Tub!

Beautiful home on the wine trail. Explore the Shawnee National Forest, Little Grand Canyon and Panoma Natural Bridge. See Giant City State Park. Enjoy near by wineries/orchards Close to Cedar Lake where you can swim or fish. Then relax in the quiet, peaceful setting. This home has been completely renovated with two bedrooms both with queen beds. A full bathroom and a spacious kitchen with everything you will need! Deck over looks 20 wooded acres with a wonderful hot tub. Pet friendly

4.95 out of 5 average rating, 106 reviews

Top guest favorite

A rustic cottage is nestled among tall trees, showcasing a natural setting during autumn. Colorful fall foliage blends with the greenery, while fallen leaves cover the ground. The warm tones of the cottage complement the serene landscape.

Place to stay in Cobden

Cobden Retreat in the Woods

Eva’s Roost Retreat Cabin is located at Center For Lost Arts near Cobden, Illinois. Uniquely crafted rustic, zen-style cottage, designed to be close to the earth & nature. Extensive, curtainless windows facing the forest & pond allow for private views: sunrise, moonrise, forest & wildlife. Yoga mat, guitar & some art supplies. Personal outdoor space with firepit & comfy adirondack chairs. Entrance to wandering trails right outside your back door. Perfect place to retreat and renew.

4.95 out of 5 average rating, 344 reviews

Top guest favorite

An outdoor seating area features a round table surrounded by four chairs, set on a stone patio. Flowering plants line the edge of a grassy space, and a door leads into the house. The clear blue sky and greenery provide a serene backdrop.

Home in Alto Pass

The Farmhouse in Rhine Valley

Newly renovated Farmhouse in Alto Pass situated between Trail of Tears State Forest and just a hike or short drive away from Bald Knob Cross and wilderness. Minutes away from local wineries. Enjoy a peaceful pause from the hustle and bustle in our private little Farmhouse. Perfect for single family or small groups. Nearby venues and activities include: hiking, fishing, public hunting, wineries, restaurants, and many other local venues and events. Hunters are welcome.

4.99 out of 5 average rating, 157 reviews

Top guest favorite

A charming cabin is nestled among trees, featuring a welcoming front porch with seating. Flower pots are placed near the entrance, and a stone border outlines the landscaped area. The sloped roof and chimney enhance the rustic appeal of the structure.

Place to stay in Makanda

Wooded Cabin near Blue Sky & Shawnee Pet-Friendly

Secluded, yet convenient. Within 5 min of two wineries, ziplining, trail heads, & I-57. Your unforgettable romantic wine country retreat or comfortable rest after hiking or travel. No TV or Wi-Fi (good cell signal though) but that is not why you’re here! Explore the vineyards, walk the trails, and drink complementary on-farm roasted coffee! Pets welcome when you add them to the reservation. We have them too! Maple Ridge Cabin : Gateway to Shawnee Wine Country

4.95 out of 5 average rating, 306 reviews

Guest favorite

Apartment in Dongola

Earnhart Carriage House

Standalone, 2 BR, light, airy, upstairs apartment for 4 guests. Full kitchen, coffee bar, washer/dryer. In our small village, there is a bank, post office, Dollar Store, library, gas station, and a park are within walking distance. I-57 is one mile. We live near a railroad crossing. If you are a very light sleeper, they may wake you. Each bedroom has a desk and sitting area and the bedside table lamp bases have outlets to charge your phone or tablet.

4.91 out of 5 average rating, 129 reviews

Guest favorite

Home in Anna

Updated Farmhouse w/ King Suite

Cozy updated farmhouse near the Southern Illinois Wine Trail and Shawnee National Forest. This warm and comfortable home blends minimalist style with rustic charm and features a King Suite, family-friendly amenities, and a peaceful, rural feel—yet it's just minutes from town. Only 24 minutes from SIU Carbondale, it’s perfect for campus visits, hunters visiting during the season, wine trail adventures, or a weekend close to nature!

4.93 out of 5 average rating, 60 reviews