Holiday rentals in Oakdale

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Top-rated holiday rentals in Oakdale

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

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Top guest favourite
Home in Ava
4.93 out of 5 average rating, 139 reviews

JGB’s Farm and Getaway

We are in the country next to a blacktop road.This is a very laidback place , there are farm animals across the road at our farm. This was my moms farm house and I just want people to enjoy it as much as she did. We are close to Kincaid Lake, the local winerie, the World Shooting Complex, and hiking trails (Piney Creek Revenue). Come and enjoy a day fishing or just sitting on the back deck enjoying the peaceful surroundings. Later build a fire and sit back and relax. Come and enjoy the country.

Guest favourite
The geodesic dome is positioned among tall trees, illuminated by the glow of a fire pit in the foreground. A staircase leads up to the entrance, under a darkening sky with early stars becoming visible.
Dome in Perryville
4.94 out of 5 average rating, 169 reviews

The Snow Globe*OffGrid DomeGLAMP*Adventurers Only

EXPERIENCE The Dome in the Woods • IMMERSE in complete silence with the absence of electricity: no hum or vibrations from this completely solar/propane fueled geodesic dome. NoAC • GLAMP in this OFF GRID ADVENTURE. 430 sq ft floor plan. 14 ft ceiling. 20 ft bay window with endless nature view at the foot of your bed. Lofted 7ft. • STARGAZE from the deck or fire pit • NESTLE in the romantic wooded nature of southeast MO. S of St Louis.N of Memphis • UNPLUG, UNWIND, RELAX. Adventure seekers only!

Guest favourite
Tiny home in Whittington
4.91 out of 5 average rating, 321 reviews

Tiny Home of Whittington

This cozy tiny home is located a little over one mile off of Interstate 57 and within two miles of Rend Lake. Whether traveling through and needing an easy one night stay or a weekend getaway, this is the place for you. Located in the quiet village of Whittington, the property has great access to the area while providing a peaceful stay on the edge of the country. Our property has multiple rental buildings, but there is plenty of parking space for anyone traveling with a pickup and trailer.

Superhost
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Fairview Heights
4.86 out of 5 average rating, 129 reviews

Wooded Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Top guest favourite
Barn in Cutler
4.85 out of 5 average rating, 26 reviews

Private, peaceful lakefront home

Enjoy a breathtaking sunrise while you relax on a private lake. This barndominium is fully equipped with modern amenities, while offering a serene experience with access to kayaks & paddle boards, as well as a mile-long hiking trail. While you are tucked away on this private oasis, you are just a short 15 minute drive to local restaurants, and grocery stores. You are also just steps away from beautiful Pyramid State Park. Perfect for couples, small friend groups, small families & pets!

Top guest favourite
The treehouse structure is elevated, supported by stilts, with large windows that reflect the surrounding greenery. The exterior features a combination of wood finishes, and warm lighting casts a welcoming glow in the evening. The pathway leads through the natural landscape to the entrance.
Treehouse in Perryville
5 out of 5 average rating, 695 reviews

Private Treehouse Retreat | Hot tub

The TreeLoft is the first of two treehouses at BaseCamp—designed for cozy seclusion, romance, and rest. Nestled in a private forest just 1 hour from St. Louis, it blends upscale comfort with immersive nature, while still being 20–35 minutes from hiking, wineries, and dining. ✨Our NEW treehouse, The TreeRise, offers an even more elevated, spacious experience at BaseCamp. Perfect for romantic getaways, anniversaries, personal retreats, and intentional escapes to unplug and reconnect.

Top guest favourite
Home in Mascoutah
4.96 out of 5 average rating, 481 reviews

The Doll House

Not suitable for work groups. Our Victorian doll house is Listed on the National Register of Historic Places, it maintains its original features yet is updated with modern conveniences. The kitchen is fully equipped. Wifi is available and the home is within walking distance of restaurants and shopping. Enjoy the peaceful backyard while you sit on the porch & relax. An easy drive 4 miles south of I-64. No third party bookings. Use of property to registered guests only.

Guest favourite
Home in Nashville
4.96 out of 5 average rating, 75 reviews

Little Nashville

Relax with the whole family at this peaceful place to stay. Stay for a night or longer in comfort of this newly remodeled home located near town. Two bedrooms with queen memory foam mattresses, high thread count sheets, with room to unpack. One bathroom with a deep soaking tub and all linens provided. Enjoy the full kitchen and eat in dining. Laundry room accessible to guests. Cozy up to the fireplace while you sink in to the deep plush couches.

Top guest favourite
Home in Pinckneyville
4.96 out of 5 average rating, 268 reviews

The Walnut House

Thank you for checking out The Walnut House. It’s a roomy and comfortable 2 bed 1 bath house in the middle of town. Within walking distance are several restaurants, many local shops, two grocery stores - one with a great deli! The city park has a walking trail, shady picnic areas, a public pool, and tennis and paddleball courts will be completed soon. Come settle in and enjoy a quiet safe small town get-away!

Superhost
Flat in Du Quoin
4.88 out of 5 average rating, 112 reviews

30 West·The View·Scenic Escape near Fairground

Step into 30 West · The View, a bright and stylish suite overlooking downtown Du Quoin. Wake up to sunlight streaming through large windows and enjoy being just blocks away from the Fairgrounds, cafés, and shops. Whether you’re here for the State Fair, exploring the wine trail, working remotely, or a quiet getaway, The View offers a light-filled space designed for comfort and convenience.

Top guest favourite
A living area features a stone fireplace against a contrasting wall. Two tall stools flank a bar space, providing a place to gather. The floor is covered in wide, wooden planks, contributing to a modern yet rustic design.
Cabin in Coulterville
5 out of 5 average rating, 13 reviews

Paradise Corner

You’ll enjoy a very secluded and peaceful relaxing setting. Perfect for a get away from busy everyday life with family or friends (or not) Canoe or Kayak on the lake. Go for a hike on the hiking trail thru the property’s 136 acres. Nap on the hammocks. Fish the 7 acre stocked lake. Your adventure awaits. Depending on your interests, this place is so much more than just a place to stay.

Top guest favourite
A serene private lake is surrounded by lush trees, reflecting a blue sky. A kayak is on the water, while a small wooden ladder leads to the water's edge. Smooth stones line the shore, creating a peaceful setting for relaxation or water activities.
Cabin in Du Quoin
4.98 out of 5 average rating, 162 reviews

H & B's...Come experience the magic of nature!

The Cabin is nestled in the woods, a few hundred feet from a beautiful private lake. If it's total solitude you are looking for, this is the place. Keyless entry makes it perfect if you want total privacy. If you want lake access, come down and have coffee with us for orientation. Our pantry items, coffee, granola, half & half, and spices are perfect for your full-service kitchen.

Popular amenities for Oakdale holiday rentals

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  2. United States
  3. Illinois
  4. Washington County
  5. Oakdale