Vacation rentals with a pool in Winchester

New Lakefront Luxury!Pool, Fire Pit, Marina, Boats

Escape to comfort and style in this brand-new home nestled in a serene, gated community on the shores of beautiful Tims Ford Lake. Take in breathtaking lake views, or stroll to the water’s edge for a day of lakeside fun. Minutes to fine dining. Exclusive guest access to the private community clubhouse featuring a spacious saltwater pool with stunning lake vistas. Located near Tims Ford Marina with easy access to daily boat and kayak rentals. In house boat and kayaks also available for rent.

The Old Fashioned @ Twin Creeks - FREE BOAT & POOL

*FREE BOAT - Any 2 or more nights booked and staying through October 31st, 2025 qualifies for one full day complimentary pontoon rental of your choosing, subject to terms & availability! This home offers a vintage vibe with a twist of sophistication. The Old Fashioned is equipped with a game room, poker tables & leather tufted sofas. Breathtaking views of Tims Ford Lake and Twin Creeks Marina right out your back door. Sit back and relax while you pour the bourbon here at the Old Fashioned.

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.

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

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Stylish 2BR Cabin C by MHM Luxury Properties

Discover the beauty of Jasper Highlands in this luxurious single-level cottage by Prairie School Craft. Thoughtfully designed with comfort and charm, it's perfectly located near top attractions and community amenities—ideal for both relaxation and adventure. - Just a 1-minute walk to Top of the Rock Brewery & Wedding Venue - A 7-minute drive to Sweetens Cove - Only 30 minutes from Downtown Chattanooga Come experience the best of Jasper with us!

Mountain High Cabin with hot tub, fire pit, & indo

Mountain High Cabin 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!

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Escape to luxury at your expansive 10,000 sq. ft. lakeview home, where every detail has been designed to create an unforgettable experience. Perfect for family reunions, large gatherings, or a lavish getaway with friends, our resort-style property comfortably sleeps 20 guests and offers a plethora of amenities that allow you to have your own private resort stay on 14 private acres.

Forest Retreat: Poolside Bliss Close to Campus

Get ready for an unforgettable stay in our fantastic 3 bedroom, 2 bath home! Its prime location and incredible outdoor spaces are perfect for university visits or weekend getaways. Plus, it's within walking distance to the campus and the trendiest eateries. But be warned, our property is so enticing, you might just end up spending all your time here!