Holiday rentals with a pool in Winchester

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

Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs

Enjoy lake living at one of the newest lakefront neighborhoods on Tim's Ford Lake. This cozy cottage is in a beautiful gated community and has lake views from the front porch. It is only a 1 min walk to the community pool overlooking the lake and direct lake access for kayaks and paddleboards that we include for you! This beautiful home also boasts a hot tub, fire pit, and game room for your family to enjoy! You are also centrally located and only 5 min from Twin Creeks Marina and downtown!

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.

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.

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.

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!

Tennessee Pearl: lakefront-amazing views-lake toys

Welcome to The Tennessee Pearl, a newly constructed 4 bedroom, 3.5 bath two-story home, with breathaking views, that sits directly lakefront on Tims Ford Lake. Restaurants and shopping are 1 mile away in historic downtown Winchester, TN. Twin Creeks Marina with restaurant and boat rental is just minutes away.

Beautiful Tim's Ford Lake House (Sleeps 20)

A beautiful southern farmhouse design with modern conveniences, our 2019 built home will be the perfect house for groups both large and small. With the ability to sleep up to 20 people, each of the 6 bedrooms offer en-suite bathrooms with a large room perfect for kids.