Holiday rentals with a pool in Winchester

4.97 out of 5 average rating, 150 reviews

Home in Trenton

Suite Retreat: Pool & Spa | Minutes to Chattanooga

Nestled in the heart of nature's grandeur, this beautiful suite offers comfort and awe-inspiring views. It's a sanctuary where modern luxury meets the tranquility of the great outdoors. Relax in the hot tub, and enjoy morning coffee in the cabana surrounded by mountain views. Make s'mores with the kids while enjoying a gorgeous sunset. This property is perfect for 2-4 guests, 5 with baby. The hot tub is open year-round & ready to melt your cares away! The pool is now closed for the season.

5 out of 5 average rating, 33 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, 3 reviews

SPF 44 Suntan @ Twin Creeks

Beautuful home located the ultimate family friendly lake community. This home is fully furnished and located in a beautiful, gated community. The Twin Creeks Lake Community offers a private dock with lake access, kayaking and rentals. Coded entry, garage, community pool and dock. Private lake access with dock Kayaking and rentals available Community pool Gated community with secure entry Garage and coded entry for added security Family vacations 🏠 Couples getaways ❤️ Outdoor enthusiasts 🌳

4.93 out of 5 average rating, 29 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. 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. On-site Parking 1 car garage + 2 cars driveway. Wheel chair n ramp access for ADA compatible! Bring your family n friends n celebrate lake life at our abode!

4.97 out of 5 average rating, 37 reviews

Barefoot Retreat w/kayaks/SUP/Game Room/Pool

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 sits close to the lake. 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 boasts indoor/outdoor fireplaces & fire pit for your family to enjoy! You are also centrally located and only 5 minutes from Twin Creeks Marina and downtown!

5 out of 5 average rating, 23 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.

4.88 out of 5 average rating, 16 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

5 out of 5 average rating, 12 reviews

Gorgeous Lakefront! Pool, Games, Fire Pit, Marina!

Relax with the whole family at this peaceful and stylish new construction home in a beautiful gated community. Gorgeous lake views abound! Simply walk outside your front door to enjoy beautiful Tims Ford Lake. Private community pool club with spacious saltwater pool overlooking the lake. Pamper yourself and relax in this spacious and stylish home made for the ultimate getaway! Next to Tims Ford Marina with boat and kayak rentals 7 days a week. Relax and unwind!!

4.93 out of 5 average rating, 122 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, 55 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.

4.86 out of 5 average rating, 115 reviews

Cabin in Bryant

Cloud 9 Cabin with an indoor pool, hot tub, & fire

SUNDAY check in ALLOWED. Cloud 9 Cabin is located inside Paradise Pointe which is gated & on a mountain at tristate corner of AL/TN/GA. Walk HIKING TRAIL to tristate corner. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck. 19 rentals has access to pool house. Cabin has WIFI, TV, electric fireplace, hot tub, charcoal grill & fire pit! Premises has basketball courts. ENJOY VIEW FROM BLUFF & POOL DECKS!

Home in Chattanooga Valley

4.91 out of 5 average rating, 115 reviews

Chatt Vistas Oasis-3bdrm-5m to TN-PoolDeckBBQFireP

Welcome to your charming country retreat! This fully furnished home offers a cozy and relaxing atmosphere with its inviting pool, fire-pit area, and a spacious, fully fenced backyard. Centrally located just 4-6 minutes from TN/St. Elmo and Lookout Mountain, it's perfect for exploring Chattanooga. The home features 3 bedrooms and 1 bathroom. Enjoy your peaceful getaway in this delightful and convenient destination!

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House rentals with a pool

4.91 out of 5 average rating, 44 reviews

Home in Walker County

Pickleball | Pool | Hot Tub | Gym | BBQ

BethRating, 5 stars1 week ago

The house had plenty of space for everyone and had tons of stuff to do. We used the hot tub, pool, pickle ball court, ping pong and poker table. We used the grill and ate on the balcony a number of times. Quiet neighborhood and close to everything. Had issues with connecting a portable camera with existing wifi but reached out to host and quick response for alternative wifi resolved the issue. Main floor beds were very comfortable. Enjoyed our stay; would come back again.

4.8 out of 5 average rating, 5 reviews

Home in Chattanooga

Quail Run Farm House, 15 Mins to Chattanooga

SarahRating, 5 stars1 week ago

We had an issue arrive that was outside anyone’s control. We lost power at check in. The host was amazing, and quickly made alternative arrangements for us. And got us back to our initial booking spot as quick as possible. Keeping us in the loop every step. They handled the situation perfectly. The power issue was not their fault. They did take immediate action, and assured we were taken care of every step of the way. Highly recommend any of the Timber Root locations. We will be back in the fall for a wedding, and will definitely use this host again. Thank you for a beautiful, and peaceful vacation home!

5 out of 5 average rating, 8 reviews

The Old Fashioned @ Twin Creeks - FREE BOAT & POOL

RichardRating, 5 stars5 months ago

Enjoyed time with friends and our little ones over new years. This was a great spot. Especially loved how many rooms had their own restroom and the upstairs area.

4.95 out of 5 average rating, 20 reviews

Home in Gruetli-Laager

Pool, Huge Backyard - Near Hiking & The Caverns

CariRating, 5 stars5 months ago

House was beautiful! Kevin was super accommodating & quick in responding to any questions we had. Would definitely recommend!

5 out of 5 average rating, 11 reviews

Charming Barefoot Bay Bungalow

JenniferRating, 5 stars10 months ago

Beautiful place looks like brand new construction, great location, everything was done with excellence!

5 out of 5 average rating, 12 reviews

Barefoot Dreams

JohnRating, 5 stars3 weeks ago

I’ve probably stayed at over 100 Airbnb’s over the years and this one is definitely in the top three overall. Fully stocked, spotless, convenient, responsive host, and just a wonderful property. Right across the street from the community pool and the lake. Literally couldn’t ask for a better place for a relaxing weekend with families.

4.79 out of 5 average rating, 19 reviews

Home in Sewanee

Forest Retreat: Poolside Bliss Close to Campus

SamanthaRating, 5 stars1 month ago

A lovely stay, beautiful, peaceful, perfect