
Vacation rentals with a pool in Winchester
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Winchester

Total vacation rentals
Explore 40 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at €78 per night before taxes and fees

Verified guest reviews
Over 1,400 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Winchester
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Private Treehouse Retreat! Sauna|Hot Tub|Pool
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.
5.0 out of 5 average rating, 108 reviews
Lakefront Haven | Hot Tub | Kayaks, Firepit
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 • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards 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
4.97 out of 5 average rating, 64 reviews
Private indoor pool & sauna
Forget your worries in this spacious and serene space. Enjoy your own private indoor pool and sauna. Relax on the porch, grill up some great grub and enjoy time with family and friends. Only 3.2 miles to Jack Daniel Distillery and 13 minutes to Tims Ford State Park. Situated close to Tullahoma, Lynchburg and Shelbyville, TN. Lots to see and do. There are nearby hiking trails, waterfalls to explore, rent or bring your kayaks and float the Duck River. Tour several distilleries nearby.
4.91 out of 5 average rating, 32 reviews
Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath
Fully furnished - a unique Tim’s Ford 3 level house! 4 bedrooms LakeHouse with 3 decks, theatre room, 2 furnished kitchens. Free Kayaks with jackets. Soak in the Sun or feel the breeze from the three decks - with breathtaking views. Next door Swimming pool n boat ramp. Twin creek Marina n restaurant - 5 mins drive. Downtown Winchester restaurants - 5 min drive. 3 cars parking + guests parking. Wheel chair ramp access. Family n friends celebrate lake life at Lakehouse! Pls declare your pets
4.88 out of 5 average rating, 49 reviews
Forest Retreat: Poolside Bliss Close to Campus
Welcome to your spring getaway in Sewanee. This inviting 3-bedroom home offers spacious living areas, serene outdoor spaces, and a convenient location near the University of the South. Walk to campus events, local restaurants, and nearby scenic trails while enjoying the fresh mountain air and blooming landscapes of the season. Whether you’re visiting family, exploring the Domain, or planning a peaceful weekend retreat, this comfortable home provides the perfect place to relax and recharge.
4.82 out of 5 average rating, 61 reviews
Private lakefront log cabin w/dock & hot tub
Be one with nature at this unique, tranquil getaway on Tim’s Ford Lake. Enjoy the two fireplaces in a “rustic” meets “modern” log cabin on 10 acres of privacy that is adjoined to over 2000 acres of park land. There is 450 ft of lake front & private dock to store your boat/toys, but the dock is not usable Nov 1 to April 1. Enjoy nature walks, spend lake time with friends or just relax taking in the amazingly beautiful views, hot tub and amenities. This truly is our happy place.
4.93 out of 5 average rating, 132 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.
5.0 out of 5 average rating, 51 reviews
Lakeside Luxe | Lake + Pool Access
Lakeside Luxe is a 3-bedroom, 2.5-bath retreat nestled in the gated Barefoot Bay community right on Tim’s Ford Lake. Enjoy lake views, access to a waterfront community pool, community kayak launch and firepit, and a private fenced backyard with a cozy outdoor fireplace. Only a two minute walk to the community lake access and pool and just one mile from charming downtown Winchester, you'll be minutes from great dining, shopping, and entertainment.
4.79 out of 5 average rating, 28 reviews
Basecamp Retreat TimsFordLake
Welcome to Basecamp Retreat! Modern lake luxury on Tims Ford Lake. This 3-bedroom, 2.5 bath cozy retreat, located in the gated community of Barefoot Bay, is the perfect home base for your visit. Offering modern comforts and convenience in a prime location with picturesque lake views, Basecamp provides a comfortable and inviting space to relax and recharge. Located 2 miles from Twin Creeks Marina & Resort and 1 mile from downtown Winchester.
4.95 out of 5 average rating, 74 reviews
Lakeside Retreat Marina/Pool, Golf Cart, Game Room
Discover luxury living at your lakeside retreat in the prestigious Twin Creeks Marina subdivision on Tims Ford Lake. This exquisite home features indoor and outdoor fireplaces, a game area with foosball and arcade, plus a 6-seater golf cart for exploring. Just minutes away, enjoy a pool and the convenience of Twin Creeks Marina's amenities, including a restaurant, boat rentals, snacks, and gas. Your ultimate vacation experience awaits!
4.94 out of 5 average rating, 69 reviews
EASY PEASY on Tim's Ford Lake, golf cart, pool
Custom designer home built by Legacy Lake Homes on Tim’s Ford Lake! Located in the gated community of Twin Creeks. Steps to the Marina and restaurant, this is a lake front home. Beautiful lake view from 3 bedrooms with upper and lower back decks. Plenty of space for 2 or more families/ multiple couples. Beautiful neighborhood pool, fire pit, and cute little putt-putt golf area. Golf cart (six seater) included with signed waiver.
4.88 out of 5 average rating, 41 reviews
Luxury 3BR lakeside escape
Discover serenity at New Latitude in Twin Creeks Village! Nestled near the picturesque shores of Tim’s Ford Lake, our 3-bedroom, 3-bathroom retreat offers a haven for relaxation and rejuvenation. Enjoy the scenic charm of Twin Creeks Village, where tranquility meets luxury just moments from Twin Creeks Marina. Indulge in lakeside living at New Latitude. Book your getaway now and experience the beauty and calm of Tim’s Ford Lake!
4.88 out of 5 average rating, 43 reviewsPopular amenities for Winchester rentals with a pool
House rentals with a pool

Secluded Luxury Farm Home, TN Whiskey Trail nearby
5.0 out of 5 average rating, 28 reviews
Waterfront Oasis On Tims Ford Lake: Pool/Kayak!
4.98 out of 5 average rating, 85 reviews
Barefoot Bungalow Bright airy lakeside home
4.9 out of 5 average rating, 29 reviews
By the pool
4.86 out of 5 average rating, 14 reviews
4-bedroom Lake house in Twin Creeks Winchester TN
5.0 out of 5 average rating, 7 reviews
Lake House Dreams
4.91 out of 5 average rating, 11 reviews
The Curlin House, Lakeside Getaway Tim’s Ford Lake
5.0 out of 5 average rating, 13 reviews
Salsa Lido@Twin Creeks Resort, The lake is calling
4.95 out of 5 average rating, 20 reviewsOther vacation rentals with a pool

Chic 2BR Cabin D by MHM Luxury Properties
4.84 out of 5 average rating, 77 reviews
Luxurious Cabin in Jasper Highlands - Blackberry
4.98 out of 5 average rating, 55 reviews
Spacious Home in “Tiny Home” Lake Community
4.96 out of 5 average rating, 69 reviews
Monteagle/Sewanee forest cottage with amenities
5.0 out of 5 average rating, 87 reviews
Hundred Oaks
4.98 out of 5 average rating, 94 reviews
Lakeside Laurel | HOT TUB • Firepit • Walk to Town
4.97 out of 5 average rating, 39 reviews
~New~ Spacious Lake House w/ Heated Pool & Hot Tub
4.93 out of 5 average rating, 28 reviews
Charming Barefoot Bay Bungalow
5.0 out of 5 average rating, 11 reviewsWhen is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €157 | €150 | €168 | €176 | €227 | €267 | €262 | €213 | €190 | €173 | €165 | €157 |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
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