Holiday rentals in Pike County

Chestnut Street Retreat

A quaint and friendly neighborhood, with large backyard for kids playing, relaxing in the breeze way with morning coffee, or fun by the fire pit. Biking or walking around the neighborhood is safe and fun on a sunny day. Though you may feel in the country you are very close to downtown Huntingburg, 8 miles to Downtown Jasper. House is cozy and relaxing for a weekend away or if you're looking for activities Holiday World (18 Miles), Patoka Lake, French Lick Casino & West Baden Hotel (27 Miles).

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!

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.

The Castle

Bring the whole family to this great place with lots of room for fun! Located 15 miles from Holiday World & Splashin’ Safari. Five minute walk to the city pool, and League Stadium, where the movie “League Of Their Own” was filmed. Also home of the Dubois County Bombers. 4 bedrooms, 3.5 baths. 4000 square feet. Above ground pool, Hot Tub, 4 Sun loungers, outdoor furniture & enclosed outdoor dining area. Spacious kitchen, Movie room, inflatable outdoor projector screen with projector.

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

Cozy, 2 bdrm home. Weekly and monthly rates avail.

Our sparkling clean home is located in a great neighborhood in the heart of Washington, IN. Our small town boasts of 1) Multiple dining options, 2) Coffee shops, 3) Shopping and entertainment. Or if you are wanting something a little quieter and at home you will find a host of 4) Outdoor games, 5) Bikes, and more in the storage building out back. So whether you are here on vacation or business our goal is to make you comfortable and at home while you are in our area.

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines Cabin. We are 12 miles from Holiday World. The Cabin has its own private hot tub and also includes a private fire pit and we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. Our other rentals are Eagles Nest (3BR option) and Eagles Nest Plus (4BR option). Starting with the 2026 season check out will be at 10 am ON SUNDAYS ONLY, 11AM all other days.

Hoosier Homestead in scenic southern Indiana

The Hoosier Homestead is nestled in the gently rolling hills of southern Indiana on historic Hoosier farmland. The beauty of southern Indiana is right outside the Homestead doorstep with scenic drives to numerous points of interest just minutes away. The Hoosier Homestead provides a cozy gathering space for your family and friends. Whether relaxing inside or counting stars by the fire bowl at night, everyone loves our Homestead. It is a great place to come together!

Country escape with game room!

Very spacious with lots of space for the whole family to come and spend time together. Enjoy time by the fire in the unique patio grain bin, or in the basement game room playing board games, pool, or darts. Enjoy a meal in the large spacious kitchen with ample seating space for the whole family, 3 separate living areas with smart tvs. 4 full baths, Bedrooms include 2 king beds, 3 queens and 4 twin beds in the basement game room storage area.

The Getaway House

Welcome to our Get Away House. Located on the edge of Loogootee, it is a very peaceful area and yet close to the local stores and restaurants. Relax with the family and spend the evening on the back patio. With two bedrooms and one bathroom, this single level home is perfect for your night away. PLEASE READ! Due to a recent storm, the back fence was damaged and has been removed and we are waiting for the new fence to be installed.

Private Suite/Sleeps 3/Center Town/Pets OK!

Guests will have their own entrance and is closed off from the rest of the house. It is a 2 room space (250sf) Has a queen memory foam bed . A bathroom and a kitchenette in the next room (with microwave, coffee maker, mini fridge, panini press) fold down couch for 3rd guest You will get much more from us than a hotel room and much cheaper! Pet fees $20 per stay $5 guest fee per day after 2.

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.