Holiday rentals in Winchester

4.95 out of 5 average rating, 394 reviews

Tiny home in Chattanooga

La Cabaña You have to climb it to get the wooness!

Pets welcome with a $35 per pet fee to a maximum of 2. Quiet mountainside tiny house on 2.5 acres in the Tennessee River Gorge will provide you with the best nights sleep. Spectacular bluff view hikes are within a few miles of the cottage. Enjoy kayaking or stand up paddle boarding along the Tennessee River with 2 rental locations within a 3 minute drive of the house. With the convenience of downtown Chattanooga only a 15 minute drive you can't miss out on everything this rental has to offer.

4.93 out of 5 average rating, 167 reviews

Cabin in Monteagle

Monteagle Mountain Serenity Nashville Chattanooga

"FAMILY CABIN" WITH SPECTACULAR VIEWS NO EVENTS OR LOUD PARTIES ARE ALLOWED. NEAR MUSIC CITY USA AND CHATTANOOGA MILES HIKING TRAILS AND NINE NEARBY WATERFALLS After a day of exploring relax on the OVER SIZED DECK PANORAMIC MOUNTAIN VISTA'S GAS FIRE PLACE , FIRE PIT & GRILL FULLY STOCKED KITCHEN KING SUITE w/CUSTOM SHOWER QUEEN BEDROOM & 3 bed BUNK ROOM ADDITIONAL FULL CUSTOM BATH 4 TV's INTERNET & cable All the beauty of The SMOKEY'S without the crowds.

Top guest favourite

Home in Lookout Mountain

4.99 out of 5 average rating, 119 reviews

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.

4.9 out of 5 average rating, 122 reviews

Home in Chattanooga

Get Away And Relax, In Private Chattanooga Home

Situated close to Chattanooga sites and adventures, guests can enjoy an afternoon of museums, shopping and dining. Things to Do in Chattanooga: Tennessee Aquarium Duck Tours Chattanooga Zoo Coolidge Park Walnut Street Bridge Creative Discovery Museum Hunter Museum of American Art Lookout Mountain Tennessee Riverpark Raccoon Mountain Caverns Ruby Falls Chattanooga Whiskey Experimental Distillery **The pet fee for this listing is $100/pet. $250 if evidence of pet without notice**

4.9 out of 5 average rating, 103 reviews

Tiny home in Monteagle

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.

5 out of 5 average rating, 3 reviews

Rare Flat Lot w/Beautiful Views, Dock, Hot Tub

Escape to this charming lakeside retreat, where stunning sunsets and unbeatable water views await! Sitting right on the water, this cozy home offers a dock with a slip, two paddleboards, two kayaks, and a hot tub for ultimate relaxation. Dine outdoors by the lake, gather around the fire pit table, or enjoy the kid's game room with foosball and an arcade. With its vintage charm and unbeatable location, this is the perfect getaway for families and friends looking for lakefront fun!

Top guest favourite

5 out of 5 average rating, 21 reviews

The Modern Mainstay at Barefoot Bay

Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.

4.82 out of 5 average rating, 157 reviews

Cabin in Winchester

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.

4.86 out of 5 average rating, 14 reviews

TC Easy Breeezee

Your home away from home a place to enjoy friends and family together under one roof, relax and enjoy, kick back and forget all your worries! We have you covered, awning for protection of sun and rain! Warm cozy beds and sofas! New furnishing throughout entire house!! Sip coffee, on our cozy outdoor furniture while listening to the pool bubblers take all your daily worries away!! Unplug, sit back and find your happy place Close to shopping, marina, dining and much more

4.6 out of 5 average rating, 5 reviews

The Mimosa @ Twin Creeks Resort w/ FREE BOAT*

*FREE BOAT - Any 2 or more nights booked and staying through May 31st, 2025 qualifies for one full day complimentary pontoon rental of your choosing, subject to terms & availability! This stylish place to stay is perfect for group trips, family reunions, or family vacations. With plenty of bedrooms, everyone will have plenty of space during their stay as well as large family rooms to get together for activities and fun!