Holiday rentals in Chester County

4.91 out of 5 average rating, 177 reviews

A two-story lakefront home is surrounded by lush greenery and well-maintained landscaping. A paved path leads toward the house, which features a large deck on the upper level and vibrant trees nearby. The serene lake is visible in the background, enhancing the peaceful setting.

Home in Lexington

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!!

4.98 out of 5 average rating, 124 reviews

The cabin is set in a secluded wooded area, surrounded by tall trees and colorful foliage. Its exterior features a combination of wood and stone, with a sloped blue metal roof. Sunlight filters through the trees, casting dappled shadows on the ground.

Cabin in Henderson

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.

5 out of 5 average rating, 12 reviews

The entrance of a quaint guest house is depicted, featuring a wooden door with decorative glass panels. Flanking lights provide illumination, and a wooden deck leads up to the entry. Lush greenery is visible in the surrounding area.

Guest house in Henderson

Hillside Haven

Relaxation is calling at Hillside Haven. From the moment you walk in the door you will feel rejuvenated in this quaint guest house. Favorite features include a comfortable king size bed, smart TV with Netflix guest access, luxuriously soft towels, fully stocked coffee bar, and a beautiful view. You’ll feel as if you’re away from it all, but are only a ten-minute drive from downtown Henderson and Freed-Hardeman University. Ideal for one couple or a small family (Max of two adults and two kids).

4.95 out of 5 average rating, 526 reviews

The studio features a comfortable queen size bed covered with a grey quilt and decorative pillows. A small desk with a chair is positioned next to the bed. Warm lighting enhances the cozy atmosphere, while a kitchenette is visible in the background.

Guest house in Henderson

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!**

4.97 out of 5 average rating, 125 reviews

The exterior of the house is displayed, featuring a modern design with an extended roof and large front windows. A stone pathway leads to the entrance, bordered by a landscaped grassy area and scattered trees in the background.

Tiny home in Henderson

“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

4.99 out of 5 average rating, 71 reviews

A charming red cottage features a wide front porch with two white chairs and potted plants. The entrance is highlighted by a decorative oval door, flanked by large windows. Surrounding trees with autumn foliage add a vibrant natural backdrop.

Home in Finger

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.

A brick ranch-style home is visible, featuring a wide porch and evenly spaced windows. The front yard displays a manicured lawn with shrubs, and the street runs closely alongside the property, providing a glimpse of the nearby commercial area.

4.89 out of 5 average rating, 90 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.

4.98 out of 5 average rating, 91 reviews

A light blue house is situated on a grassy area, surrounded by lush trees. A covered porch is visible, along with a welcoming wreath on the front door. The flat lawn offers ample space for outdoor activities, enhancing the peaceful rural environment.

Home in Finger

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.

5 out of 5 average rating, 128 reviews

Double glass doors framed in a vibrant yellow provide access to the space. A wooden chair complements a dining area adorned with a soft table setting. Exposed brick walls and natural light enhance the warm, welcoming atmosphere.

Home in Finger

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!

A serene lake is framed by vibrant autumn foliage and tall trees, reflecting the colorful surroundings. A white fence runs along the edge, enhancing the natural beauty of this tranquil scene, inviting peace and relaxation.

5 out of 5 average rating, 134 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!

A renovated single-story home with a white exterior is framed by blossoming pink magnolia flowers in the foreground. The entrance is marked by a small set of steps leading to a welcoming door, surrounded by grassy areas and mature trees.

5 out of 5 average rating, 41 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.

The front view of a remodeled home showcases a two-story structure with a metal roof and white exterior. Large windows are framed by wooden accents. A pathway leads to the entrance, with a small pumpkin placed on the porch, surrounded by bare trees in the background.