Holiday rentals with outdoor seating in Winchester

Hip in The TreeTops 10 wooded acres /King Size Bed

A truly unique inviting one of a kind mountain retreat in a quiet rural spot on 10 acres. This private home features a wonderful kitchen with 2 bedrooms & 2 baths on secluded wooded acreage for a peaceful getaway. The interior features a beautifully modern & open floor plan flooded with natural light with high ceilings and floor to ceiling oversized windows. The 2 large decks with a luxurious hot-tub will leave you feeling your hanging out in the treetops. Enjoy & Chattanooga only 11 miles away

Top-of-the-Falls Glamper

Stunnningly located on the bluff above a huge waterfall. Miles of trails and hundreds of acres to explore right here on the property. Eight State Parks within a half hour drive. World Famous Fiery Gizzard Trail Head is just 10 minutes away. Disclaimer: Waterfall flow is subject to fluctuations in temperature, seasonal droughts, & rainfall. Optimal waterfall flow seasons are fall, winter & spring". Camp shower closed in winter. Propane heater/fireplace & propane provided at extra charge.

The Jade | HotTub & Pool, Family Friendly Stay

Located in the heart of Historic Saint Elmo, 10 mins from Downtown Chattanooga (Tennessee Aquarium), the trendy Southside (Chattanooga Choo Choo), Ruby Falls, Rock City, & Incline Railway. Unwind and connect with friends and family in our insta-worthy, beautifully designed home. Easily walkable to food & drinks or coffee & ice cream. Over 2250 sq ft, comfortably sleeps 10 adults in 4 bedrooms/ 3.5 bath. A 5 person hot tub, 30 ft pool, ping pong table, yard games, a private bar, and fire pit!

Fiery Gizzard Homeplace & Cottage

A private cottage located close to area restaurants and outdoor activities. Approximately 5 minutes to FIERY GIZZARD trailhead as well as dining in Monteagle and Tracy City. Our cottage has a private courtyard where you can grill, chill, and make a fire! A large custom walk-in shower with great water pressure and endless hot water. A large smart tv with excellent internet. Very comfortable bedding and a nice leather recliner. Snacks and drinks in the refrigerator are complementary.

Sweet Dee's Tiny Home

FEATURES A HOT TUB! Relax in style at Sweet Dee's (formerly listed as The Alexander), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

Cozy tiny home ☆Sleeps 4 w/ great outdoor space

Relax & unwind at our tiny home located in Tracy City Sleeps 4-Queen bed in private bedroom & upstairs loft Covered deck w/ gas firepit Campfire in backyard Electric fireplace inside Outdoor obstacle course for kids Fully stocked kitchen 3 Tv's, DVD players & DVD's Fishing poles Great restaurants and shops Bike and hiking trails nearby Kayak & canoe rentals Gas grill 90 min from Nashville, 45 min from Chattanooga, & 15 min from the University of the South in Sewanee.

The Roost, Glamping at large, Up! with the trees.

This luxury glamping site is nestled on the west skirt of Signal Mtn, TN. Sitting atop the hill is The Roost - an eco friendly camping site with the comforts of a hotel: A/C, attached shower & bathroom, private driveway & parking, and breathtaking views! Only ten minutes from downtown Chattanooga. Kayak rentals available within a mile, and endless hiking trails nearby. If disconnecting for a couple of days is your goal, you've found your private oasis!

Creekside at Rutledge Falls

Cozy nest right on the creek. Lots of privacy. Hiking trails and Waterfalls nearby. Listen to the water from a porch swing overlooking the creek. We have a double recliner for movies and popcorn. This efficiency apartment has a private entrance with private covered porch and a full kitchen. Work area with Wi-Fi. Pets are welcome - must be free of fleas and ticks.

Spectacular Mountain Top Cabin Getaway

Overlooking four mountain ranges, with a private lake,this executive cabin offers serenity and privacy like none other. If you enjoy cooking, friends and family...this is the place! Enjoy a huge deck with a hot tub and outdoor fireplace. Inside and outside dining with spectacular sunrise and sunsets. Fifteen minutes from Dunlap and an hour from Chattanooga Tn