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Holiday rentals in Oakland City

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Top-rated holiday rentals in Oakland City

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Cabin in Winslow

4.9 out of 5 average rating, 256 reviews

Primitive Historical Escape with Modern Amenities

If you desire an escape from the bigger city life and want to slow things down a bit with a place that makes you feel like you have went back in time to a simpler time, while still being close to it all, then this cabin getaway is your destination. Our cabin is perfect for a family weekend retreat, anniversary celebrations, and hunters. We are excited to be able to continue to maintain this historical building and still be able to offer it as a place for people to enjoy and stay in to this day.

Guest favourite

Home in Winslow

5.0 out of 5 average rating, 19 reviews

Twin Lakes

Twin Lakes has a unique location on 60 acres in between 2 wildlife filled lakes stock with fish and wild geese flying in and out. A habitat for deer, squires and rabbits. The house is located down a long drive off the county road in a rural area. Very peaceful to sit on the back deck in the morning and enjoy a cup of coffee and watch the wildlife. Fishermen are invited to enjoy the lake from lakeside or small boat. The home is very comfortable with 2 queen size beds and a futon. Enjoy & relax!

Guest favourite

Loft in Huntingburg

4.93 out of 5 average rating, 130 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Guest favourite

Flat in Evansville

4.99 out of 5 average rating, 345 reviews

Historic Home Apt B: 3 Blks to Haynie's Corner

Location, location! This private 1BR/1BA luxury apartment is located in downtown Evansville on coveted First Street. Guests will have the privilege of experiencing a unique atmosphere whether they are in town for business or leisure. This architecturally diverse street is filled with historic mansions, giving it character that is unmatched in any other neighborhood in Evansville. Our 1850 home is nestled in this quiet residential historic district with local bars/restaurants blocks away.

Guest favourite

Home in Newburgh

4.96 out of 5 average rating, 116 reviews

The Cottage on W Main

Family friendly 2 bed 2 bath! Charming and convenient space in downtown historic Newburgh. Easy walk to the scenic riverfront and downtown area which includes ice cream shops, restaurants, shopping and hair salon. Short walk to beautiful Rivertown Trail! Come explore downtown Newburgh and with easy access to multiple sites in Evansville the location is fantastic! So many family amenities with no stairs inside house, stroller, pack-n-play, outlet covers, kids books, and highchair provided!

Guest favourite

Home in New Harmony

5.0 out of 5 average rating, 119 reviews

The Angel Carriage House in New Harmony

Cozy and elegant, located in the heart of historic New Harmony, this 1920's carriage house was reimagined, expanded, and tastefully furnished as a stand-alone guest house in 2016. It includes a fully equipped kitchen, roomy bedroom plus queen-sized sofa bed in the living room, two full baths, hi-speed WIFI, three HD TVs, a private back porch with one of the best views in New Harmony, and heated & A/Ced garage. Relax and recharge, just one or two blocks from the town's key attractions.

Guest favourite

Cabin in Derby

4.95 out of 5 average rating, 249 reviews

Derby Escape

Welcome to the rolling hills of Southern Indiana. Your escape from the day to day grind awaits. Our cabin was built in the 1800's and reassembled (with modern conveniences) in 1996. Ideal for the hunter, hiker, boater or fisherman. Thousands of acres of Hoosier National Forest, the Ohio River and it's tributaries all provide a one of a kind outdoor recreation experience. Or you can just sit next to the fire, enjoy the night sky and relax! Either way... Welcome to Derby.

Guest favourite

Farm stay in Paoli

4.97 out of 5 average rating, 155 reviews

Brambleberry Farm Off-Grid Cabin

Our non-electric cabin in the woods is the perfect glamping opportunity. This rustic retreat is a 5-8 minute walk from our house and parking lot. The 270 square foot tiny house has a queen mattress in the loft, a wood stove for heat, cooking facilities including a propane cook top and gravity fed rain water (non-potable). Large windows look out over a beautiful southern Indiana holler. Camp shower & composting toilet. Experience comfortable, tent - free camping!

Guest favourite

Cottage in New Harmony

4.99 out of 5 average rating, 305 reviews

New Harmony Cottage

Open concept cottage w lots of space for one or two located in the Historic District of New Harmony. Free street parking, a sitting area and comfortable queen bed. Washer/Dryer and a small kitchenette (no stove or cooktop.) WiFi and and a Smart TV for your convenience. Bring your Netflix or Hulu passwords. Be our guest in your own space. Easy no contact checkin & checkout. Coffee/Tea bar or Black Lodge Coffee! *FYI check Winter hours for shops & restaurants.

Guest favourite

Cabin in West Salem

4.99 out of 5 average rating, 102 reviews

Lake Cabin in the Woods

Looking for a relaxing getaway? Passing through the area and need a place to stay? Seeking peace and quiet in a remote area? Then look no further, Lake Cabin in the Woods is the place for you! Located approximately 60 miles from both Effingham, IL and Evansville, IN, our cabin is off the beaten path but is still accessible to highways and interstates to guide your midwestern travels.

Guest favourite

Loft in Newburgh

4.98 out of 5 average rating, 154 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. 2 complimentary drip coffees are included with your stay.

Guest favourite

Cabin in Gentryville

4.96 out of 5 average rating, 124 reviews

The Cabin - Near Holiday World & Splashin' Safari

If you'd like a true log cabin feel while staying on a beautiful, serene wooded 10 acre plot of land, this is the place for you and your friends/family! This small cabin has been reconstructed after being transferred to this location by the owner and his son. All of the decor and fixings are antique in style to fit the log cabin feel, to bring you back to the good ole days.

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Other great holiday rentals in Oakland City

Guest favourite

Home in Vincennes

4.96 out of 5 average rating, 82 reviews

Cheerful 3-bedroom home with huge yard

Guest favourite

Home in Vincennes

5.0 out of 5 average rating, 35 reviews

Ernie's Place

Guest favourite

Guest house in Tennyson

4.96 out of 5 average rating, 67 reviews

Guest House with acreage to explore.

Guest favourite

Home in Vincennes

4.95 out of 5 average rating, 83 reviews

Cozy Two Bedroom Home

Guest favourite

Flat in Fort Branch

5.0 out of 5 average rating, 8 reviews

Corporate Cottage "B"

Guest favourite

Cabin in French Lick Township

4.99 out of 5 average rating, 77 reviews

Serenity Acres

Guest favourite

Home in Olney

4.94 out of 5 average rating, 36 reviews

Lakeside Lodge with Private Dock and Kids' Kayaks

Guest favourite

Cabin in Eckerty

4.93 out of 5 average rating, 76 reviews

Stairway to Heaven

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