Holiday rentals with a pool in Winchester

Family Fun - Private Pool, Spa & Mountain Views

Welcome to a beautifully designed lower-level guest suite. From the moment you step inside, you’ll notice that every detail has been thoughtfully curated with your comfort in mind. Unwind in the hot tub, splash in the pool, end the day making s'mores with the kids as the sun sets. This property is perfect for 2-4 guests, 5 with a baby. "Paradise. We could not have asked for more. The suite was beautiful and stocked with everything we needed... The pool and hot tub were so relaxing." - Heidi

Wooded Writer's Retreat with Pool

Book NOW for family pool fun get-away. A peaceful health-conscious 3-bedroom tri-level at the ft. of Lookout Mtn. 2 fireplaces. Upper 2 levels are yours exclusively. Lower level office not accessible. Advanced air purification system. Bottled water NOT needed with reverse osmosis filter. Ideal for families, small retreats, or parents of students. Covenant College is visible from the kitchen & attractions minutes away. Plan ahead for Spring-Summer. Open pool season. No pets allowed.

Fish Tales Cabin – Spacious Retreat with Hot Tub

Perched atop a scenic bluff in Bryant, AL, Grant Summit Cabins offers nine charming cabins overlooking Nickajack Lake. Each cabin features panoramic mountain and water views. With a variety of layouts and sleeping capacities, there’s something perfect for romantic getaways, family vacations, or group retreats. Whether you're sipping coffee on the porch or exploring the nearby hiking trails, relaxation comes easily here. Grant Summit Cabins blends comfort & nature for an unforgettable stay.

Cozy home for up to 10 guests on LkMt GA

Welcome to our very quiet and lovely neighborhood, our cozy house is located on 5 acres off of a private road. Forest and pasture with plenty of space between neighbors. Our 4 BR house is a wonderful place for families. The pool is closed for the off season of OCT- MAY. Garage and apartment above garage are not included in the rental, occasionally this apartment is owner occupied, it has it's own deck and separate entrance, your privacy will be well respected during your stay.

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!

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.

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.

I Fly Cabin: Watch Hang Gliders /Paragliders Soar!

Welcome! The cabin is located at the base of Lookout Mountain Flight Park. Watch hang gliders take off and land from the front windows or deck. Have fun!! ~maybe even take a tandem flight yourself! There is also no better place to hang wait! Hang waiting is when you wait until the conditions are right to fly hang gliders or paragliders. Once the weather is flyable, enjoy a front row seat to the south side tandem takeoffs!

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!

Big Time Hill Cabin with an indoor pool, hot tub,

Big Time Hill is located in Paradise Pointe, a gated mountain retreat at the tri-state corner of AL/TN/GA. Hike the trail to stand in three states at once! Enjoy access to the huge indoor pool house with a communal hot tub, two indoor slides, an outdoor deck, seating, and more. All 19 rentals share these amenities. Plus, enjoy two small basketball courts, sand volleyball, horseshoes, and more for endless fun!

Latitude Adjustment - Lake Cottage

Enjoy the lake with all the amenities you could dream of! At Twin Creeks resort & Marina offers three resort style pools, marina, restaurant all golf cart accessible, designer decorated home with all the comforts of home. Enjoy sunsets on the lake, fires at the firepit, grilling on the patio, hiking around the resort. Family friendly with fold-a-away crib, toys, books and other things to entertain children.

Lookout Mountain Retro Pad

Peaceful, mid-century bluff home with valley, city, and Blue Ridge Mountain views from the East Brow of Lookout Mountain! An outdoor fire pit, two indoor wood burning fireplaces, a bluff side pool, and outdoor seating to enjoy the beautiful views & singing birds. Open kitchen floor plan, natural light, and four bedrooms to comfortably accommodate up to 6 guests (up to 8 guests for immediate family).