Holiday rentals in Anna

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Top-rated holiday rentals in Anna

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Guest favourite

Guest house in Carbondale

5 out of 5 average rating, 203 reviews

Homestead Cottage

Enjoy tiny farmhouse life in this adorable 375 sq. foot cottage. Loaded with everything you need this little cottage is nestled privately behind some trees on our 11 acre farm. You will soon forget how close you are to town with the beautiful view from your windows and the pasture fence just steps out the back door. Whether you’re here for the wineries, amazing hiking, an SIU event (3 miles) or to visit with family, the Homestead Cottage will provide a comfortable retreat from any adventure.

Guest favourite

Cabin in Alto Pass

4.99 out of 5 average rating, 248 reviews

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!

Guest favourite

Place to stay in Makanda

4.94 out of 5 average rating, 198 reviews

Maple Ridge Cabin at Panther’s Rest

Secluded, yet convenient, we’re within 5 min of two wineries, ziplining, trail heads, and I-57. This is your unforgettable romantic wine country retreat or comfortable rest after hiking or travel. There is 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! Your pet is welcome when you add them to the reservation. Maple Ridge Cabin is your gateway to the Shawnee Wine Country!

Guest favourite

Barn in Cape Girardeau

4.96 out of 5 average rating, 150 reviews

Under the Stars - Farmhouse

Enjoy the tranquility of this modern farmhouse charmer! Custom built minutes from downtown Cape. Relax outside around the fire pit, roast marshmallows and watch the sunset. Finish the night with a long soak in the hot tub. Start the morning on the front porch rocking chairs and take in a sunrise. Open concept, fully equipped kitchen, 3 Bd. including King master/full bath, 2 Queens with full guest bath. Near Trail of Tears and walking distance to classic dive bar/burger joint

Guest favourite

Farm stay in Makanda

4.87 out of 5 average rating, 132 reviews

Farmhouse Cellars @Feather Hills Vineyard & Winery

Located on the Shawnee Hills Wine Trail, Farmhouse Cellars is located within our working winery at Feather Hills Vineyard & Winery. You have the opportunity to look in on the wine making process while enjoying a quiet, comfortable place to rest your head. This is a large space with open kitchen, living and sleeping areas. The front porch offers a beautiful sunset while looking over the vineyards and you are but a short walk from our tasting room where you can enjoy a tasting.

Guest favourite

Home in Alto Pass

4.99 out of 5 average rating, 115 reviews

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.

Guest favourite

Treehouse in Makanda

4.97 out of 5 average rating, 247 reviews

Panthers Inn Treehouse

Come nestle amongst the leaves at Panthers Inn Treehouse. This secluded, well equipped, elevated cabin has the perfect combination of natural beauty and artful luxury. Isolated yet conveniently located 2 minutes from Blue Sky and Feather Hill wineries, within 5 minutes of Panthers Den hiking trail and the Shawnee Hills canopy tour and only 10 min from I-57 exit 40. Panthers Inn is the perfect starting and ending point to your Shawnee Hills Wine Country vacation!

Guest favourite

Place to stay in Cobden

4.94 out of 5 average rating, 294 reviews

Eva’s Roost Retreat -Center For Lost Arts

A private retreat space, Eva’s Roost 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.

Guest favourite

Cabin in Cape Girardeau

4.92 out of 5 average rating, 219 reviews

Log Cabin w/ Hot tub - Near Casino & Downtown Cape

THE BEST GETAWAY HERE IN CAPE! Have a relaxing staycation here in Cape Girardeau Perfect for a QUICK GETAWAY for couples, families or friends 5 MINS to the casino, country club and downtown cape Very unique log home with a private bedroom queen size bed, pull-out queen size futon in the living room and twin size hide away SLEEPS 6. Pool table, darts, and a hot tub.There is a large deck and fire pit which has the feel of being in the woods.

Guest favourite

Cabin in Anna

4.87 out of 5 average rating, 139 reviews

Contemporary Glamping with Native American Appeal!

Luxury Glamping with a taste of Native America! Stay in a hand-hewn oak timber cabin, on the historical "Trail of Tears" in Union County, Illinois. This lodging offers the rustic appeal of an authentic cabin in the woods, with the all the creature comforts and all year around outdoor hot tub. *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #1.

Guest favourite

Cabin in Alto Pass

4.91 out of 5 average rating, 147 reviews

Hutchins Creek Cabin -2br- Wine Trail & Wilderness

Hutchins Creek Cabin is located along spring-fed Hutchins Creek, surrounded by Shawnee National Forest Wilderness Areas, and at the south edge of the Shawnee Hills Wine Trail. Featuring an open floor plan with 2 bedrooms and 1 bath, it can comfortably sleep 4-6 adults. Regardless of weather conditions, our cabin offers multiple outdoor living spaces including a fire pit, multiple decks, and a screened-in porch.

Guest favourite

Home in Dongola

4.97 out of 5 average rating, 138 reviews

Spacious Home in Country Setting

READ ENTIRE DESCRIPTION BEFORE BOOKING!!! Retreat in this spacious home, tucked into a quiet natural setting. The second story deck extends the full length of the front of the house, giving a lovely view of the peaceful surroundings. With no television or other technological distractions on the premises, this home is perfectly suitable for quality time with your loved ones and can accommodate large families.