Vacation rentals with a pool in Winchester

5 out of 5 average rating, 65 reviews

Treehouse in Sewanee

5 Acres! Cozy Nature Retreat

Imagine sipping your coffee while watching the deer pass through 5 acres of forest from our steam sauna. Imagine enjoying a private marked path on property or hopping in your car to hike a 9 mile, 5 hour trail just 15 min from home, then recovering in the hot tub. If you want a private city escape, our shipping container treehouse is for you! PRIVACY NOTE: There are ZERO shared spaces, no on else on property. While we live in a 'neighborhood' you cannot see another home from our treehouse.

5 out of 5 average rating, 40 reviews

Lakefront Haven on Tims Ford w/ Kayak and SUP

Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Spa Getaway • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, Paddleboard and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

5 out of 5 average rating, 14 reviews

Stunning Lakefront Escape! Fall Specials!

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.

5 out of 5 average rating, 11 reviews

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.

5 out of 5 average rating, 17 reviews

Townhouse in Winchester

Lovin Lake Life

Relax and unwind at this spacious 5BR/7-bed townhome just 1-2 minutes from Twin Creeks Marina & Dry Creek Beach! Take the complimentary golf cart and relax by the pool or head to the marina to rent a boat, shop at the store, or eat/drink at Drafts & Watercrafts Bar & Grill. Enjoy cozy furnishings, relax on the screened in porch, or challenge your group to a game of ping pong. This home is perfect for families, groups, and lake lovers looking for a fun and easy getaway in Winchester, TN.

5 out of 5 average rating, 32 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.

4.91 out of 5 average rating, 22 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

4.95 out of 5 average rating, 21 reviews

Barefoot Bungalow Bright airy lakeside home

Relax in this beautiful lakeside home in Barefoot Bay. Gated community with its own pool and kayak launch. Enjoy views of Tim’s Ford Lake while being conveniently located near downtown Winchester. Spacious open concept kitchen, living and dining area with fireplace. One bedroom and full bathroom downstairs. Three bedrooms and 2 full baths upstairs with bunks in one room. Fire pit, along with kayaks and paddle boards for your pleasure and 2.3 miles to Twin Creeks Marina.

4.93 out of 5 average rating, 128 reviews

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.

4.93 out of 5 average rating, 43 reviews

Cabin in Jasper

Cozy 2BR Cabin D by MHM Luxury Properties

Experience the scenic charm of Jasper Highlands in this luxurious single-level cottage, just 30 minutes from downtown Chattanooga. Perched on Jasper Mountain, it offers stunning mountain and river views—perfect for a peaceful and comfortable getaway. - A 1-minute walk to Top of the Rock Brewery & Wedding Venue - A 7-minute drive to Sweetens Cove - Just 30 minutes to Downtown Chattanooga Relax, unwind, and explore all that Jasper has to offer!

4.99 out of 5 average rating, 81 reviews

Cabin in Monteagle

Hundred Oaks

Clifftops cabin close to the front gate. Nearby lake, bluff view, waterfalls, hiking. Sewanee University 3-4 miles away. Chattanooga-30-45 min, Nashville-90 min. Important: the stairs leading to the loft are very steep so it’s probably not the best option for young children or the elderly. We do not allow for any pets on the property. During the winter months from Christmas to March, the washer/dryer will be unavailable due to freezing weather.