House vacation rentals 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

Near Caverns & Sewanee 2-bed/2-bath w/EV charger

2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped kitchen. The "Farm View" house offers country views with privacy. A serene place to relax, unwind and retreat while enjoying pastures and country views. "EV/Tesla wall charger", Starlink internet w/ YouTube TV and streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester. Easy drive less than 7-mi to University of the South, and just 10-miles/ 10-12 min to The Caverns Concert Hall.

Tims Ford *FreeUTV/kayaks/canoe*2.5 acres/private

Welcome to your retreat at Tims Ford Lake! Hidden away on 2.5 acres, surrounded by trees, complete privacy with no neighbors in sight! Enjoy peace and quiet, TVA land between you and the lake. Plenty to do..whiskey trail, fishing/kayaking Elk River, boating Tims Ford Lake to name a few! 16 minutes to Jack Daniel's Distillery Property is less than a mile from boat ramp! Ride the UTV down to the lake! ***IMPORTANT: For UTV & craft info, please see below in Other Things to Note for details.

Sunset Cottage +Dock on Tims Ford Sleeps 12

Welcome to Sunset Cottage, a spacious and serene lakeside escape nestled in the heart of Winchester. Located less than a mile from the town square, this charming cottage offers both the tranquility of lakefront living and the convenience of nearby dining and shopping. Relax as you take in breathtaking sunset views from the back covered porch. With a private boat dock, you can easily set out for a day on the water. Designed for comfort and relaxation, Sunset Cottage is the ideal getaway.

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

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!

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.

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

WHATAVIEW Lakehouse and Dock on Tims Ford Lake

WHATAVIEW Lakehouse is a 3-story, architect-designed house with uninterrupted views of Tims Ford Lake, Goose Island and Maple Island. It offers spacious, air-conditioned accommodations for one or multiple families. With its private dock, this quiet part of the lake offers safe swimming, boating, skiing or tubing, and fishing right off of the dock. Spectacular sunsets and the expansive views combine to make WHATAVIEW a memorable place to spend your vacation.