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Vacation rentals in Olmsted

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Top-rated vacation rentals in Olmsted

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of a charming house is displayed, featuring a red and white color scheme. A covered porch with a swinging bench is visible, along with a flag pole supporting an American flag. Two windows allow natural light to enter the home.
Bungalow in Karnak
4.99 out of 5 average rating, 153 reviews

Trails End Tunnel Hill Bike Trail Overnight Stay

Located at the end of the 58 mile Tunnel Hill Bike Trail. Fully furnished with full size kitchen, bathroom with shower, bedroom and pool table. No need to pack, all the basic essentials are provided including, but not limited to, bottled water, paper plates, utensils, towels, soap, shampoo, toothpaste, coffee, juice, milk, bread, etc. If it's not there, the Dollar General Store is located 5 blocks away. Full size bed, room for 2 additional people, inflatable mattress available upon request.

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
5.0 out of 5 average rating, 103 reviews

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.

Guest favorite
The custom-built treehouse is elevated on stilts, surrounded by greenery. A spacious deck features a railing, offering access to the entrance. Steps lead to the ground below, while large glass doors enhance the connection to nature.
Treehouse in Cape Girardeau
5.0 out of 5 average rating, 209 reviews

Twisted Sassafras Treehouse

A custom-built treehouse located on 10 acres with a water view that you can take in from the hot tub on the deck! It is nestled high in the trees and is the perfect romantic getaway for two! Feel like you are away from it all without being away from it all! This treehouse is located on a county road just minutes from Cape Girardeau. Enjoy catch and release fishing on site, local wineries, shopping in historic downtown Cape Girardeau, local restaurants, gambling, historical sites & more!

Top guest favorite
Cottage in Vienna
4.96 out of 5 average rating, 167 reviews

Peaceful Cottage Retreat

Contactless Check-in. This cottage has everything you need for a relaxing getaway. It's private, tranquil setting is surrounded by nature. A King bed with luxury bedding ensures a peaceful stay. The cottage comfortably accommodates 4 adults with the additional sleeper sofa. The kitchen includes a mini-fridge, microwave, toaster and coffeemaker. Also enjoy the cozy gas fireplace inside the cottage. Outside you'll find a large patio, gas grill, wood burning firepit, and a shady hammock .

Top guest favorite
A living room features wooden accent walls and large windows that frame views of the surrounding woods. Comfortable reclining chairs are positioned with a soft throw blanket draped over one. A small table with a lamp adds warmth, inviting relaxation. Natural light fills the space.
Cabin in Dongola
4.98 out of 5 average rating, 45 reviews

Edgewood Retreat

Perfect country retreat for a small family or two couples! Cabin living room and patio space overlooks the edge of the woods. Two comfortable bedrooms with queen beds. Master bedroom has attached full bath with tub / shower. Guest bedroom has access to second full bath with corner shower just outside bedroom door. Closets in both bedrooms! The living room has a beautiful working gas Mendota Hearth fireplace. Rustic hickory kitchen with built in laundry unit! Relax, enjoy, unwind!

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
4.91 out of 5 average rating, 171 reviews

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.

Top guest favorite
A cozy living area features a white fireplace with a wooden mantel. A television sits atop the mantel, framed by a floral arrangement. A patterned armchair is positioned nearby, complementing the neutral tones of the walls and flooring.
Home in Kevil
5.0 out of 5 average rating, 98 reviews

Hosta House

Enjoy an adult stay in this private cozy getaway. This entire space is single level, quiet and just minutes from Paducah. (Outdoor kenneling accepted no indoor pets.) The country setting is ideal for a quiet weekend or longer stay. The private patio is a perfect place to have your morning coffee and evening wine while enjoying the flowers and sunsets. You will enjoy the roomy space and French touches no matter the reason for your visit. Summer grounds boast over 100 hosta varieties.

Top guest favorite
A modern farmhouse is depicted at sunset, featuring a welcoming entrance with a covered porch. A stone pathway leads to the front door, bordered by a grassy lawn that extends to fields and trees in the background.
Barn in Cape Girardeau
4.94 out of 5 average rating, 272 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

Top guest favorite
Dome in Stonefort
4.99 out of 5 average rating, 145 reviews

Modern Dome in Shawnee Forest with Hot Tub

Old Colorado Glamping Dome is nestled deep into the woods surrounded by beautiful tall pines. It is heated and cooled and has all the necessities as a typical house. We also packed as many amenities as we could into this property including an oversized 6-Person hot tub, 500 MBPS fiber internet, outdoor tv, fire pit table, Weber grill, hammock swings, custom bathroom with rainfall shower, full kitchen, coffee bar, king & queen sized beds, bean bag toss, board games and much more!

Top guest favorite
The treehouse is elevated on wooden stilts, surrounded by lush greenery. A wooden deck with a railing extends from the entrance, creating a welcoming outdoor space. Large windows brighten the upper level, while a sun art piece adorns the side of the structure.
Treehouse in Makanda
4.96 out of 5 average rating, 448 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!

Top guest favorite
A serene cabin sits amidst lush greenery, surrounded by trees that reflect in a tranquil pond. A well-kept lawn leads up to the entrance, enhancing the peaceful setting. Blossoming branches frame the scene, adding a touch of nature’s elegance.
Cabin in Cobden
4.96 out of 5 average rating, 141 reviews

Unique luxury cabin with fireplace and pond view

Shawnee Pond Retreat is a two-bedroom countryside haven that sits on a ridge in the Shawnee National Forest. Located just outside Alto Pass near numerous vineyards, lakes and hiking trails, it is a perfect destination for friends, couples, or families. Shawnee Hills Wine Trail has 11 wineries nearby. With its impressive bluffs and spectacular trailways, Giant City State Park is just a 15-minute drive.

Guest favorite
A charming exterior is presented, featuring a vibrant blue facade and white trim. A welcoming porch is highlighted by steps leading to the front door, with an American flag displayed proudly. Lush greenery surrounds the entrance, adding to the inviting appearance.
Home in La Center
4.96 out of 5 average rating, 24 reviews

La Center country house

This is our vacation home from busy lives. It has been completelly renovated. Your family will be enjoying 4 bedroom 2 bathroom house with amazing fully stock kitchen and fenced in backyard with patio. Grocery 2 min walking distance. Also couple local restaurants within walking distance. This is trully amazing house with everything you need!!

Popular amenities for Olmsted vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Pulaski County
  5. Olmsted