House holiday rentals in Winchester

Dog/Family Friendly Mountain Gem near Attractions

Looking for a family and pet-friendly getaway? Look no further than The Sweet Retreat! Your cozy and comfortable vacation rental is located just off Scenic Highway and close to popular attractions, including Ruby Falls, Covenant College, Rock City, and 8 miles to Chattanooga. You'll love our high-speed internet, comfortable beds, multiple TVs, stocked kitchen, fenced yard and outdoor fire pit. With so much to see and do in the area, you'll love making The Sweet Retreat your home away from home.

Open concept, peaceful porches, quiet, clean !

Quiet, wooded, peaceful, spacious home on Lookout Mountain. Open concept floor plan with full laundry. Fully furnished kitchen for those that like to cook with a large refrigerator and dishwasher as well as an island with extra seating. Each bedroom has at least one large bed and TV. Large screen TV in family room.All TV's include Netflix.There is an outdoor basketball hoop, grill and lots of parking. Chattanooga is only 10-12 miles away. Near hiking, hang gliding, rock climbing and Rock City.

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!

Star Cottage 2

Cute Modern- Rustic pet friendly home close to all Chattanooga has to offer! Places to eat and Walmart just down the road. The house is 5 minutes from Lookout Mountain attractions, downtown, TVA (Raccoon Mtn.), hiking, biking trails, and boat ramp. Newly remodeled and furnished with most everything you might need! Has a fire pit and electric fire place. Pets welcomed but must be approved before booking. Please message me if you plan to bring your pet before you book. Hope to see you soon!

Hilltop Hideaway

Enjoy a unique blend of nature and city life in this newly renovated home surrounded by Conservancy land and quietly perched overlooking the highly sought after and historic St Elmo neighborhood. This home is minutes from downtown Chattanooga and a short stroll to the Greenway and trailheads on Lookout Mountain. The light, airy design of the home blends a smart style and natural elements to create a clean and inviting space for relaxing, adventuring, or reconnecting with friends and family.

Fire Lake Estate *NEW* Hi Speed Internet!

All fresh, new and ready for guests, this completely renovated lake home with gorgeous water and sunset views will amaze you and leave you breathless as you watch the famous Fire Lake sunset from almost every room in the house. Located conveniently just minutes off interstate I-24, centered 1 hr from Nashville and 1 hr from Chattanooga and Only 8 miles from Bonnaroo Music festival. Bring your boat or kayak as the small neighborhood is located right next to a boat ramp and swimming area.

Southern Comfort Lakehouse on Tims Ford Lake

Tims Ford Lake is the best family vacation all year and we have the best view on the lake. We're on Lost Creek with 4 bedrooms, a bunk room, 3 full baths, game room, 2 large decks, a dock with a Hydrohoist and Jet Ski lift. Our cove is off the main channel so no direct boat traffic. It's 10 minutes from Jack Daniels Distillery and the State Park with hiking/biking trails and the fabulous Bear Trace Golf Course. We're on a cul-de-sac in a secluded neighborhood with the best sunsets.

Boutique St Elmo Farmhouse 7 min from Downtown

Beautifully remodeled Farmhouse originally built in 1887. Experience a piece of local Chattanooga history while letting your stress melt away in this tranquil house. Only a 5 min walk to the incline, excellent coffee shops and restaurants. This amazing home has tall ceilings, huge windows and stunning light filled spaces. Hang out in the huge kitchen/dining area while the rest of your group relaxes in the adjoining living room. Only a 7 min drive or Uber to downtown Chattanooga.

Swallow's Nest with a Hot Tub!

The Swallow's Nest on Lookout Mtn is just 8 minutes to Covenant College, 12 mins to Rock City, 15 to St Elmo, and 25 to downtown Chattanooga. Set on a large tract of land with beautiful 270 degree views, our house is beautifully set up for couples, families with kids, or family gatherings. We're just moments from Mtn Biking, Hang Gliding, Lula Lake Land Trust, and Cloudland Canyon. Take the short drive to Chattanooga, TN for many other activities and great food scene.