Holiday rentals with outdoor seating in Winchester

Time Well Wasted at The Retreat at Water's Edge

Trendy yet traditional, Time Well Wasted offers a space that is as cozy as it gets. Rain or shine, host an exceptional evening on the screened deck, which overlooks private, wooded scenery and features two super comfy egg chairs, a dining set, plus an outdoor sofa. Prefer a night under the stars? The property also offers a firepit area situated on a spacious, stone patio for roasting marshmallows and campfire meals. So, pull your shoes off and stay a while. Here at The Retreat at Water's

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.

Serene Mountain Retreat: Hot Tub & Pizza Oven

Embark on a serene escape to the picturesque Serene Mountain Retreat, just a brief 20-minute drive from downtown. Delight in amenities such as a hot tub and a newly installed Italian pizza oven, perfect for cozy evenings. With two bedrooms, two bathrooms, and a fully equipped kitchen, this cabin offers comfort and convenience. Nestled amidst nature's embrace, the cabin's wrap-around porch invites you to unwind and soak in the tranquil mountain ambiance. Note: No Kids Allowed in Hot Tub

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.

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

Serenity By The Falls - Monteagle Tiny Home

Welcome to Serenity by the Falls! Located in the Retreat at Deer Lick Falls in beautiful Monteagle, Tennessee on the Cumberland Plateau. This tiny home features rustic decor and is set into a wooded lot. You'll enjoy: Coffee (Keurig), TVs for evening movies, Wi-Fi, washer/dryer, single use bathroom amenities, charging stations for electronics, firepit with Adirondack chairs, hammocks, a huge deck with bluetooth speakers, porch swing, dining table and gas grill!

Cabin in the Sky with an outdoor kitchen!

Cabin in the Sky/Treehouse is located in Paradise Pointe, a gated mountain retreat at the tri-state corner of AL/TN/GA. Hike the trail to stand in three states at once! Enjoy access to the huge indoor pool house with a communal hot tub, two indoor slides, an outdoor deck, seating, and more. All 19 rentals share these amenities. Plus, enjoy two small basketball courts, sand volleyball, horseshoes, and more for endless fun!

Private upstairs studio with quiet deck.

Keep it simple at this peaceful and centrally-located space.Has microwave and coffee maker and medium size refrigerator. There is a small dining table. The bath has a full tub and shower. Private entrance with concrete driveway and accommodating parking. Secure environment. There are stairs leading up to the space. The front window gets morning sun and the rear deck is mostly shaded.