Holiday houses in Chester County

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Top-rated holiday rentals in Chester County

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Top Guest favourite

Home in Lexington

4.91 out of 5 average rating, 174 reviews

Pine Lake Lodge (Country Lake Home)

Great 2 story lakefront home on 500 acre lake located in West Tennessee in a private subdivision 5 miles from town on a 2 acre lot . Home is 2500 sq. ft. with 3 bedrooms , 2 bathrooms , living room open to kitchen with large fireplace, enclosed porch and large open patio (40'x30') on second story overlooking lake. Large sun room extends the entire length of the back of the house upstairs for a beautiful view of the lake. Relax with a cold beer and watch sunset from dock over lake. Home is conveniently located half way between Memphis and Nashville (about an 1.5 hours from each). The house is perfect for special events such as family reunions.Or just come out for the weekend with that special someone and spend some quality time together. Bring the family pet , they are welcome too!!

Top Guest favourite

Cabin in Henderson

4.98 out of 5 average rating, 116 reviews

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.

Top Guest favourite

Guesthouse in Henderson

4.95 out of 5 average rating, 522 reviews

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!**

Top Guest favourite

Tiny home in Henderson

4.97 out of 5 average rating, 113 reviews

“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

Top Guest favourite

Home in Finger

4.98 out of 5 average rating, 64 reviews

Harvey House

20% off of stays 8-28 days! Enjoy this newly built spacious space in a country setting. We are located 15 minutes from the TN River (any boaters out there?) and Kentucky Lake and Pickwick Dam are close by as well. Boat/trailer parking is available on site. We are also a short drive from Chickasaw and Pinson Mounds State Parks, Shiloh National Park and K&M Shooting Complex. For guests with pets, we have a small, medium, and large crate for your use if/when pets must stay in the cabin alone.

Guest favourite

Home in Henderson

4.89 out of 5 average rating, 89 reviews

Nice mid-century brick home near FHU, shopping

Safe and convenient 1960's brick ranch style home is located 3/10 mile from Freed-Hardeman University. Large yard with off-street parking in back. Spacious and quality built with hardwood floors and tile baths. Located on a main street, so there is the possibility of some traffic noise. It is also near shopping, groceries and an easy walk to the downtown area. Guests will have access to the entire house with the exception of the owner's storage bedroom. There are no shared spaces.

Top Guest favourite

Home in Finger

4.98 out of 5 average rating, 88 reviews

Grannies Country Farm House

We are 12 miles from FreedHardman College, 4.2 K n M shooting range , Chickasaw State Park 18 miles, Buford Pusser museum 16 miles,Piney Lake 20 miles.Grannies house sits on a 300 acre farm nice and cozy !!!! Lots of room to park if u have a trailer or trucks ,air conditioners in each room nice brand new beds king,2 twins,2 double. 1 queen blow up mattress.If you make reservations for 4 and 6 comes you will be charged 60.00 a head . So come and enjoy ur self in Granny’s Country Farm House.

Top Guest favourite

Home in Finger

5 out of 5 average rating, 120 reviews

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!

Top Guest favourite

Home in Henderson

5 out of 5 average rating, 129 reviews

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!

Top Guest favourite

Home in Henderson

5 out of 5 average rating, 37 reviews

Rhodes Home of Henderson

Feel like you're relaxing at grandma's house with a peaceful stay in the country — only 1.5 miles from downtown Henderson. This completely renovated home retains its 1944 charm, while providing you with modern comforts, spacious walk-in tile showers, all new appliances, great mattresses, washer, dryer, fast WiFi and an open floor plan. Reserve this home at a cost comparable to two hotel rooms, and enjoy privacy, space to gather and cozy areas to relax or nap alone.

Guest favourite

Home in Henderson

4.91 out of 5 average rating, 108 reviews

Peaceful Sears, Roebuck and Co. Mail Order Home.

Come and stay at a freshly remodeled cozy home built in the 1940’s. The home has two bedrooms with living room with pull out couch, a galley style kitchen, dining room and bathroom with large walk in glass shower and soaker tub. Two Smart 55” TV’s in the home and WiFi access for your work. We are centrally located to Freed Hardeman University and downtown Henderson. Only 20 minutes from Jackson. Follow us @kenzley holdings

Guest favourite

Home in Henderson

4.96 out of 5 average rating, 25 reviews

Carole’s Cozy Cottage

Welcome to Carole’s Cozy Cottage! Only 3 miles away from Freed-Hardeman University and downtown Henderson, this home is very close to all restaurants, shops, boutiques, and other things that Henderson and Chester County have to offer. It is also 15 minutes away from downtown Jackson and 25 minutes off of I-40. This 1,000 sq foot inviting house, built in 2021, is a 1-bedroom, 1.5 bathroom home with an open floor plan.