Holiday rentals with a pool in Trenton

Sunset Haven 4BR + Pool + Hot Tub + Fireplace

Nestled on historic Missionary Ridge (10 mins from downtown), this cozy home offers panoramic views of Lookout Mountain, downtown Chattanooga, and the Tennessee river. This spacious 4 bedroom home @ 3300sq ft holds stunning views from every room of the house. MAIN FLOOR: Master w/full bath + Screened in porch, Living + Dining + Kitchen (open layout), gas fireplace + half bath DOWNSTAIRS: Queen Suite, Queen Bedroom, Bunk room, Full Bath, Laundry Room OUTDOOR: Large deck, Pool, Hot Tub, Garden

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.

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

Lookout Mountain Retro Pad - last booking Nov ‘26

📅 Last date to book: November 2026 as we are wrapping up our “hosting career”! It’s been a pleasure to meet & host others, and we look forward to our last couple months! 🏡 Mid Century bluff home with views of the rolling Georgia and Tennessee mountains. Open kitchen floor plan, natural light, and four bedrooms to comfortably accommodate up to 6 guests (up to 8 for immediate family). We are best suited as a QUIET & peaceful retreat. We are located in a full time residential neighborhood.

Riverwalk Retreat• Spacious• Pool • 5 min>Downtown

Centrally located near Chattanooga's most popular attractions, this newly decorated, Riverwalk Retreat has everything you’re looking for! -Community Pool -Neighborhood Riverwalk access (16 miles of paved trailhead along the Tennessee River) -5 minute drive to the Incline Railway, Ruby Falls and Southside Eateries -8 minute drive to the Aquarium -10 minute drive to Rock City Additionally, your retreat is conveniently located near local coffee shops, hiking, boutiques, breweries, and Publix!

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.

15 Acre Group Retreat•Full Size Pool•Hot Tub•Sauna

Luxury farmhouse on 15 private acres, custom built for the trip your family will never forget! Peaceful, and ideal for reunions or a weekend escape. • 6BR / 6BA, sleeps 12 (extra beds available upon request) • Full-size pool, hot tub & sauna • Fire pit & BBQ grill • Fast Wi-Fi • Near Rome Tennis Center & Jarrod’s Place Bike Park • Pet friendly • Convenient to Atlanta & Chattanooga • Small weddings up to 50 guests welcome (There is an additional cost for weddings, inquire for details)

Scenic A-Frame | Pool, Hot Tub & Panoramic Views

Bella Vista A-Frame offers a peaceful getaway on Lookout Mountain in Menlo, GA. Relax on the spacious deck with mountain and pool views, enjoy the hot tub, or take a dip in the seasonal pool. This cozy A-frame is the perfect blend of comfort and serenity. ➤ Sunset/Sunrise Views ➤ Large Deck w/ Overlooks ➤ Full Kitchen ➤ BBQ Grill ➤ Hot Tub ➤ Firepit ➤ Seasonal Pool (May 1st–Oct 1st) ➤ WiFi ➤ In-Unit Laundry Escape to Bella Vista for a tranquil mountain getaway!

Quiet A-frame cabin w/pool ~ perfect for families!

This NEWLY RENOVATED, Modern A-frame Mountain Cabin is only 7 minutes from I-75 with beautiful views! 5 bedrooms, 3 bathrooms, and currently sleeps up to 12. The outdoor pool is perfect to relax by during the summer! Amenities Include: o Fully stocked kitchen with appliances o 9 beds o Over 2700 sq ft o Washer + Dryer o 6 decks with seating throughout and gorgeous views o Smart 65” TV o Pool Table o Outdoor Pool: Open May-Oct o Quiet area surrounded by nature

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|5mtoTN|PoolDeckBBQFirePit

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!