Vacation rentals in Bolivar

The Natchez

Surround yourself with style in this standout space. Conveniently located close to Natchez Trace State Park and 7 recreational lakes. Our charming home is 9 miles from I-40, Parker’s Crossroads Battlefield, Veterans Cemetery, 39 miles from Shiloh National Park and 30 minutes to TN River. If you are wanting to see Memphis Legendary BBQ & Blues or Nashville Hot Chicken & Country Music, we are half way between the 2 cities. This home is near local industries and minutes from restaurants/shopping.

Cox Cabin “Cabin in the Woods”

Relax in this large, secluded multi-family cabin nestled on the outskirts of Chickasaw State Park on Cagle Trail. 2 King, 1 Queen, 2 Twin beds, Futon and plenty of space for personal air mattress for extra sleeping. Ride in/ride out to miles of trails in Chickasaw State Forest. Very secluded and private cabin with plenty of parking and trailers accessible. Minutes to Chickasaw Golf course, State Park amenities, and Henderson the home of Freed Hardeman Uni. We are pet friendly for a FEE per pet.

Romantic Cottage at JP Coleman * Pickwick * Iuka

New Build Tiny Home just minutes from the lake. Newly added hot tub!!! Nestled in nearly two acres of scattered hardwoods, enjoy this taste of heaven in peaceful bliss. This cabin would be a great place for a romantic getaway weekend. Located just 0.8 miles from the famous JP Coleman State Park, it would also serve as a great place for fishermen. The circle drive provides room for spacious boat parking without maneuvering in tight spaces. Enjoy your next lake stay in our little taste of heaven.

Peaceful Getaway In Charming Tiny House

Welcome to a truly extraordinary accommodation option—an unforgettable stay in a charming tiny house on wheels! Nestled amidst a serene and peaceful landscape, this unique space boasts a remarkable foundation enveloped by lush greenery. Take a walk through the wildflower gardens and enjoy the nature! In the area: 26 min to Chickasaw State Park 37 min to Shiloh National Military Park 33 min to Cogan's Farm 27 min to Big Hill Pond State Park 52 min to Pickwick Landing State Park 45 min to I-40

Studio Apt on 5th

The Studio on 5th in Henderson, TN is close to Freed-Hardeman University (3/4 mile) & 25 min. from Jackson. This studio w/ 1 queen size bed, 1 bath & kitchenette guesthouse is good for couples & solo adventurers. It is located in a quiet neighborhood next to the host's family home. Includes: Off-street parking, complementary coffee & snacks, Wi-Fi, soaps, shampoo, fresh towels & linens, & outdoor seating. **Simple Check in & Check Out! No "to do" lists!** **Super hosts for over 6 years!**

“The Casita Bonita”

Welcome to “The Casita Bonita” The pretty little house on 130 acres of pure bliss. My wonderful husband Jeremy and I bought 130 acres a few years back and is what we call “our farm” we have had countless picnics and bonfires, Just dreaming of doing something special on our land one day. That is where “The casita bonita” dream came true & it is our pleasure to be able to host guest just like you. I hope you enjoy your stay and the views of our land. Come back to see us soon. Love,Jeremy & Missy

The Outskirts

Take a break and unwind at this peaceful oasis. Quiet country studio cabin located on the outskirts of Ripley. Conveniently located 5 miles from The Red Barn event venue, 8 miles from Ripley's First Monday Flea Market and 15 miles from Blue Mountain Christian College. Only minutes away from Bennet Lake Hunting club and Dumas Lake. For dining: Enjoy a delicious meal at Simmer on Down Steak house 3.5 miles away. For Essentials: Dollar General and Clarks Country Store are only 3 miles away.

La Banque Stylish and comfy stay

Historic bank built in the 1920's restored to it original beauty. Located 5 min from Hwy 45, 8 min from K&M shooting complex and 15 min from Henderson. This is a perfect location for anyone wanting a weekend getaway or a place to rest and reset. Our space reflects peace and quiet, plenty of books to leaf through, a fireplace to warm your feet and a fully stocked kitchen. Spacious bathroom with a beautiful clawfoot tub to soak in. Come get the unique experience of sleeping in bank vault!

The Oliver Lakehouse

Nestled in the rolling hills of Chickasaw State Forest, the Oliver House is located on 38 acres with 2 lakes, 2 kayaks, 2 canoes and the sweetest muscovy ducks you will ever meet. Oliver is the oldest duck the inspiration behind our name! Our place is the perfect place to unwind, unplug and to just be in nature. Whether you prefer fishing, napping on the swing or reading a good book out on the deck, we are sure you’ll find it all here. Take a deep breath, relax and enjoy. We welcome you!

The Shiloh Retreat

Love being outside but don't love tents to sleep in at night? Come to The Shiloh Retreat for a relaxing place to stay on over 12 acres only 2 minutes from Shiloh National Military Park, 18 minutes from Pickwick Lake, 12 minutes to the Tennessee River, and 13 minutes from Adamsville, Tn home of Bufford Pusser. - Plenty of space to park your boat or trailer. - Smal kitchenette with refrigerator, sink, and a microwave oven/air fryer combo.

Tiny treehouse

The tiny treehouse is located on a family family. There is a lake for fishing. It is a short hike from the property through open trails. Bring your fishing poles and tackle for a fun trip on the lake. Sit by the fire pit and have s'mores and enjoy the peace and serenity of the outdoors. This is a quiet , private place to get away from the noise and rush of the city.

The Bedroom in the Barn

Welcome to Smith’s Farm Horseshoe Haven. A wonderful place to step back to the times of days gone by, where life is a little slower and simpler and enjoy a stay in our rare little gem "The Bedroom in the Barn" Lose yourself in the country, unwind and smell the fresh air and listen to the sounds of horses around you. A sweet experience you won't forget!