Holiday houses in Jennings

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

Artesian spring house Sleeps 4 Fire pit by creek

Completely renovated 1950s cottage! This home features 2 Bedrooms ,1 queen and one queen coil spring futon and full 2 baths. Guests can unwind with all of the amenities of home! Fire pit by the creek, bbg on the deck! Just minutes from Downtown Spencer, with several local destinations , Main Street Coffee, Civilian Brewery, and hiking at McCormicks Creek state park or Greens bluff nature preserve ! Finish it off at Owen Valley winery, with desert ! We look forward to hosting you at or home!

Maria’s Haven

Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

Cozy Lofted Cabin (#3) at Cataract Lake Getaway

This new cabin on a private road is a serene setting perfectly blending rustic charm and modern comfort. Only a half-mile from Cataract Lake, quick and easy access to boating, fishing, kayaking, etc. awaits! Numerous nearby attractions are sure to provide great experiences (Cataract Falls, C Bar C Event Center, Exotic Feline Rescue Center, state parks, brewery/winery, local shops/eateries, etc.) And of course, simply enjoying time in and around the cabin itself is a fulfilling getaway!

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

Cascade Cabin

Welcome to Cascade Cabin, our home away from home and yours! The charming log cabin is where a cozy rich wood aesthetic meets modern comforts. The beautiful remote cabin sits on 4 acres and is surrounded by mature trees and two glistening ponds. Enjoy your day exploring the nearby Cataract Falls and spend your evening around a bonfire. Enjoy the beautiful nature escapes that southern Indiana has to offer. We hope that you can enjoy this stunning getaway as much as we do!

Woodlands at Countryside Estates

Escape to nature in this charming tiny glamping cabin nestled near Cagles Mill Lake. This peaceful retreat sits near the end of a private lane in Countyside Estates, surrounded by a rustic woodland setting, perfect for those seeking solitude, camping with modern conveniences or a quiet getaway. It’s located near the public boat launch for Cagles Mill Lake to enjoy many water sport activities. (1.9 miles) The cabin is also close to Lieber State Rec Area and Cataract Falls.

Swans Nest

If you are looking for a place to get away from the stresses of life this is it. You can fish on our 10 acres lake, walk thru the woods or just relax on the porch swing. Only 5 minutes from the nearest town, 30 minutes from Terre Haute and 40 minutes from Indy. Front porch faces a walnut tree grove and back porch faces 10 acre lake. At least 3 State Parks are within 20 miles of this property. Also super close to the Parke County Covered Bridge Festival.

Red Cedar Log Cabin | Hot Tub! + Pet-Friendly!

Cozy, secluded, and full of charm, Red Cedar Log Cabin is the perfect Brown County getaway for couples. Soak in the private hot tub, unwind by the wood-burning fireplace, and enjoy the peaceful wooded setting. With rustic character, modern comforts, and easy access to Nashville, trails, shops, and local dining, this cabin is made for quiet mornings, cozy nights, and unforgettable weekend escapes. Book your stay and experience Brown County at its coziest.

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

Captain Bill’s Lake House Heated Salt Water Pool

Captain Bill’s Lake House. This majestic A-frame is at the entrance to the Cataract Lake boat ramp. The house will accommodate up to 7 guests, with three bedrooms and two full baths. All guests have full access to Captain Bill’s shared heated salt water pool and surrounding gardens. Boat parking is available on the property, inquire for details. Heated Salt Water Pool is seasonal beginning May 1, through September 30th.

Carriage House 1 bedroom loft suite w/ fireplace.

Keep it simple at this peaceful and centrally-located loft. Carriage House Guest Suite is located in a quiet neighborhood just five blocks from the courthouse square. Spencer's historic downtown offers the restored Tivoli theater, restaurants, art galleries & shops. Two miles from beautiful McCormick's Creek State Park and 3 miles to Owen Valley Winery. A convenient 20 miles to downtown Bloomington & Indiana University.