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Holiday rentals in Evansville

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Top-rated holiday rentals in Evansville

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

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Guest favourite
A single-story home is set on a green lawn, featuring a light brown exterior and a neatly maintained pathway leading to the front door. Windows with red and white accents provide a welcoming touch, while trees line the background, offering a sense of privacy.
Home in Bloomsdale
4.91 out of 5 average rating, 250 reviews

Hop off the highway, Relax!

Relax with the whole family at this peaceful place to stay. We are located only 4 miles off of highway 55! There are two bedrooms and two COMFY couches if you have more than 4 staying the night! This is located on a secluded road with two other homes occupied nearby by with quite, but very friendly, residents. This home is 25 minutes away from the historical town of Ste Genevieve, take a look! The host is will be able to assist you almost immediately, whether it be over the app or in person!

Guest favourite
A charming street scene captures the historic architecture of Ste. Genevieve. Colorful storefronts line the sidewalk, featuring a gallery and residences, while seasonal flowers add vibrancy. Trees with remaining leaves provide a natural canopy over the pavement, leading to parked vehicles in the distance.
Home in Ste. Genevieve
4.94 out of 5 average rating, 197 reviews

"Little Brick House" (Hael House built in 1865)

Best downtown location!! Take a trip back in time at this cozy, centrally-located brick cottage in historic Ste. Genevieve. The original home of John and Francesca Hael in the 1860's, you won't find a more authentic old town experience than you will get at "the little brick house" on Main Street. Enjoy mornings at the local coffee shops and bakeries (right across the street) and evenings on the back porch with a glass of wine. The Little Brick House has all the amenities with old world charm!

Top guest favourite
A modern kitchen features a spacious granite countertop and light cabinetry. Natural light from a nearby window brightens the space. An inset view displays a vibrant arcade area with several vintage arcade games, creating a playful contrast to the kitchen's sleek design.
Home in Ste. Genevieve
4.97 out of 5 average rating, 199 reviews

Downtown home + Arcade 1980's experience!

If you’re looking for a unique experience to enjoy with your friends and family you have found the right place! Peaceful and centrally-located place with a front porch view of the Gabouri creek and train trestle. Downtown shops and restaurants within walking distance. 1 King, 1 Queen, 1 Full bed. 1 bath with shower + 1 bath with tub. Arcade with 11 vintage games, pinball, and Shooting Gallery! Most games set to free play! *some take coin* *No parties - access limited to guest only*

Top guest favourite
The charming exterior of a light blue house is framed by lush greenery. A welcoming porch adorned with decorative flags, potted plants, and a sign greets visitors. The well-maintained lawn features manicured bushes, enhancing the inviting atmosphere of this peaceful setting.
Bungalow in Ste. Genevieve
4.98 out of 5 average rating, 136 reviews

Dove’s Nest: Serenity & Comfort Sleeps 6

Check in at 3pm. Check out 11am Code upon arrival High speed AT&T 18MBS Family friendly, couples, girls trip. Owners of the Cozy Haven tiny house rental Airbnb. next door. And Wrens Landing found on Airbnb to rent Downtown. Shops, wineries, restaurants,bars. People travel all over to experience town and french culture. Oldest settlement west Mississippi river. Coffee bar and teas. 65 inch smart tv. Each bedroom has Roku smart tv. Outside firepit & dining area. No pets.

Top guest favourite
The historic stone farmhouse features a traditional design with multiple windows and a pitched roof. The exterior is complemented by grassy areas and a pathway leading to the front porch. Surrounding trees provide a natural backdrop, enhancing the rural setting.
Farm stay in Bloomsdale
4.96 out of 5 average rating, 165 reviews

FUNKS INN-no extra guest fees or cleaning fee

This house was built in 1870, it is a stone structure and was used as a family farm home. It has been remodeled for its use today. It is historically correct, which includes antiques of the time. Post Civil War era, furniture including the beds of this period. Another interesting aspect, is that the floors are all original. Mattresses, blankets pillows, bedding and towels are all new. The wine cellar that we have added, made on location. I always leave some out for guests. No fee.

Top guest favourite
A cozy sitting area is surrounded by wooden walls, featuring a large window that offers views of the forest. A red chair stands next to a small side table, while a gray couch is positioned against the wall. Decorative art pieces adorn the space.
Tiny home in Cobden
4.95 out of 5 average rating, 123 reviews

Tiny House of Paul - Center For Lost Arts

Perfect if you're working or spending time exploring Southern Illinois. Great discount for longer stays. Tiny House of Paul house has a cozy & spacious feel. A large west-facing window looks out onto the forest. Windows in the loft open to tree tops & stars. Private inside. Centrally located on the property of Center For Lost Arts near Cobden, Illinois. Wander the trails at the end of a work day, or relax on the deck after hiking or exploring. Enjoy your time in Southernmost Illinois.

Top guest favourite
The exterior of a chalet is illuminated at night by warm string lights. Large windows reflect soft interior light, revealing a cozy atmosphere. The wooden deck is accessed by a railing, creating a welcoming entry. Trees are visible in the background, adding natural charm.
Home in Dittmer
4.96 out of 5 average rating, 579 reviews

Honeymoon Suite at Camp Skullbone In The Woods

Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

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, 682 reviews

Romantic Treehouse Retreat w/ Hot Tub

The TreeLoft is a secluded luxury treehouse designed for rest, romance, and reconnection. Nestled in a private forest just 1 hour from St. Louis in Southeast Missouri, it blends upscale comfort with immersive nature. Located 20–35 minutes from hiking, wineries, and dining, this peaceful retreat invites you to unplug, slow down, and reconnect in intentional privacy. Making the TreeLoft perfect for romantic getaways, personal retreats, anniversaries, or creative escapes.

Top guest favourite
A charming brick cottage is situated along a brick-lined street, adorned with vibrant greenery and flowering plants. The entrance features a light green door framed by lush plants, while large windows provide a glimpse of the inviting interior.
Cottage in Belleville
4.96 out of 5 average rating, 549 reviews

The Historic Garfield Inn

Welcome to the Garfield Inn. A cozy cottage off a brick-lined street in an historic Belleville neighborhood. Coffee, tea, hot cider and chocolate are provided. We are in walking distance to downtown Belleville, and free parking is available. The neighborhood is quiet and peaceful. There is a barbeque grill, covered back patio, gazebo and lovely gardens. Small well-behaved dogs are welcome. Enjoy your privacy The light is always on. We can't wait to see you.

Top guest favourite
The historic log cabin features a traditional wood exterior, accented by a sloped roof and a welcoming front porch. Two rocking chairs and vibrant flower pots are positioned at the entrance, set against a tranquil landscape. Soft lighting enhances the inviting appearance as dusk approaches.
Cabin in Ste. Genevieve
4.98 out of 5 average rating, 217 reviews

Sassafras Creek Cabin

Historic log cabin circa 1840 moved to property June 2020. Take a step back in time with furniture and decor to match the cabin’s time period. Located between two houses in newly formed Ste. Genevieve National Historical Park. It is a 10 minute walk to the main part of downtown and other historic tour sites. Adjoins Early American gift shop called Sassafras Creek Originals which is housed in the circa 1850 Brooks house. Close to wineries, biking and hiking.

Top guest favourite
The rock cottage is set amidst trees and autumn foliage, featuring large windows that glow warmly in the evening light. A chimney rises from the side, and natural vines adorn the exterior, blending the structure with its serene surroundings.
Cottage in De Soto
4.97 out of 5 average rating, 144 reviews

Rock House Retreat

Unplug and enjoy a slower pace of life at this picturesque rock cottage. The 1920’s former hunting lodge was built from stone sourced from the property, and is as charming as ever. Enjoy an early morning stroll on one of the many hiking trails, or just relax on the porch while sipping coffee. There are many great hiking opportunities within a short drive, however, once you get settled in you may not find a reason to leave.

Guest favourite
The charming exterior of Nora's Nest features a blue facade with black shutters and large windows. A modest tree stands in front, with outdoor seating arranged on a gravel path, allowing guests to enjoy views of the surrounding area.
Flat in Ste. Genevieve
4.83 out of 5 average rating, 247 reviews

Norah’s Nest

Nora’s Nest is nestled Beside and Upstairs, over Stella and Me Cafe. The space has a 2nd bedroom upon request, see full description. There is a tiny courtyard in front, for enjoying a bit of the outdoors and the activity on N. Main St. We are walking distance to many historical homes, gift shops, and other restaurants. The space has a bohemian charm with lots of personal touches you’re sure to enjoy!!!

Popular amenities for Evansville holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Randolph County
  5. Evansville