Holiday rentals in Pickens

The Point at the Rez | Spacious Waterfront Getaway

Welcome to your lakeside escape perfect for families, friends, and unforgettable memories! Nestled on a serene half-acre peninsula just steps from the water, you’ll enjoy panoramic views and endless opportunities for fishing, kayaking, and bird watching The main level includes a King primary suite and additional Queen bedroom. Upstairs, each bedroom has both a Queen bed and a Twin-over-Full bunk Whether a weekend getaway or a longer vacation, this is the kind of place you won’t want to leave!

“Paradise”

This beautiful, cozy, secluded, 2 bed/2 bath home gives you the feeling of being in the mountains! It features a fully equipped kitchen, plunge pool, hot tub, 2 outdoor bars, cooking area with a charcoal grill. It is surrounded by over 2,000 sq ft. of outdoor deck!! This property also has a mother in law suite with 1 bedroom, 1 bath, kitchen and sitting area that can be added for an additional $100/night. The property is located behind a private gate. Come relax and enjoy “PARADISE” today!

The Loft, A Little Bluestem Farm-stay

The Loft at Little Bluestem is located on a family-owned working flower farm. Our farm is located just off the historic Natchez Trace Parkway, approximately 45 minutes north of Jackson. We love this place -- from the bluestem grass that grows in our pastures, to the egrets and herons that call our little ponds home -- and we are excited to be able to share these little wonders with you, so that you too can wake up to the sounds of sheep, walk among our flowers, and fish in our pond.

Relax in Architecture! Secluded, Safe, and Serene.

Welcome to the Falk House! Listed on the National Register of Historic Places by the US Department of the Interior, the Falk House is a treasure of mid-century modern design. We've transformed the original art studio into a stylish, private oasis, with expansive views of nature and Eastover’s Upper Twin Lake. You will be central to all metro destinations, including amazing restaurants, bars, and shopping, as well as area hospitals, courts, and businesses. Long stays ideal.

The Betterton Place - 3 Bed 2 Bath Cozy Cottage

Located in the heart of Kosciusko, MS on E Jefferson St, this 50’s era house has been completely remodeled with newly tiled kitchen floors and bathrooms, granite, exposed tongue and groove ceiling, new furniture and appliances throughout! King bed in master suite. King and Queen in the guest bedrooms. If you’re coming to Kosciusko, stay in the comfort of a clean, SMOKE-FREE, home that is centrally located to everything! Have a better stay… at The Betterton Place!

The Craftsman Cabin

Take it easy at this unique and tranquil getaway. The Craftman's cabin is a large rustic cabin on over a 100 acre homestead bordering the Natchez Trace Parkway. Overlooking a pond it has front and back porches with a private setting. Enjoy a quiet getaway with Historic French Camp's local coffee shop and dining within a mile. Nestled among hardwoods this scenic spot is a hideaway from the bustle. Come experience it for yourself. Book your getaway today!

The Lazy Wolf

Welcome to The Lazy Wolf! This family-friendly 3-bedroom, 2-bath cabin is perfect for weekend getaways or long, relaxing stays. Enjoy lake views from the screened-in patio, ideal for morning coffee or evening gatherings. The back yard offers, a grill, swing set, fire pit and pier. The property is located near a public boat ramp. Whether you’re looking to unwind or make memories on the water, this cabin has everything you need for a perfect stay.

Mrs. Lillie’s Summer House

Mrs. Lillie’s Summer House is a spacious, up-to-date home that’s perfect for families and groups looking for comfort and room to spread out. Inside, you’ll find a welcoming space with modern touches and cozy furnishings. Outside, enjoy plenty of open space for relaxing, playing, and gathering around the fire pit for memorable evenings. Thoughtfully designed for comfort, this home is ideal for making lasting memories together.

The Riff House, 2 bedroom guest suite with balcony

The Riff House is a modern luxury guest house above The Guitar Academy in historic downtown Kosciusko. Originally built in 1880 as a hardware store, this building housed Hammond's Hardware for 80 years. This unit is a 2 bedroom one bath suite with a large balcony overlooking the court square. Amenities include refrigerator, microwave, coffee pot, and washer and dryer. This is an upstairs unit without elevator

Lindsay's Cottage

Relax with the whole family at this peaceful place to stay. This is a newly remodeled home. Three bedroom, 1200 square ft., 1.5 bath, plus two car garage. Has a fenced in back yard for your privacy. Has one queen bed in the Master bedroom, a full in the second and a twin in the small bedroom. It’s 2.5 miles from the nearest Dollar General and 4.5 miles from Walmart.

TreeLoft

Beautiful fully restored studio loft with 360° views of treetops, minutes from Natchez Trace and Reservoir, located in Madison County. Access to 100 acres including 2 ponds for fishing. Minutes from the Natchez Trace and Reservoir. Also, return to the classics with a record player and album collection, CD player with CDs and VCR player with tons of old classic movies.

Private Cabin• Fish • Firepit• Ponds •Nature walks

Escape to 50 private acres of peace and quiet. Fish two private ponds, enjoy nature walks, birdwatch from the porch, and unwind around the fire pit under the stars. Inside, you’ll find a beautifully remodeled cabin, coffee bar, and homemade sourdough cinnamon buns ready to bake. Just 6 miles from the Natchez Trace—perfect for a romantic getaway or peaceful reset.