Vacation rentals in Sherwood

The Historic Gipson House Caverns Favorite!

135 guests, 135 five star reviews! This is an historic house. Completely remodeled with modern convenances. Book now for 2026 caverns dates ! Top shelf accommodations ?You’ve found them ! See our reviews ! Guests love the Gipson House ! Private home and property ! Caverns 4 miles/10 mins away. Circa 1930, beautifully appointed Gipson House in scenic Pelham Valley between Chattanooga/Nashville, area has world class hiking , also near Sewanee Recognized super host and guest favorite

Whippoorwill Retreat Treehouse

“Come, Relax, & Write Your Own Story” **NO SERVICE FEES** Whippoorwill Retreat is a romantic, family-friendly real treehouse in the treetops 20 minutes from Chattanooga. This peaceful escape offers floor-to-ceiling views, a sunrise perch, outdoor fireplace, fire pit for lazy nights, and outdoor soaking tubs with Whippoorwill-scented salts, Alexa for music, and a chandelier. Sleep in a suspended bed or the Canopy Suite, a view of the stars awaits. Write your fairytale at Whippoorwill Retreat.

The Laurel Zome - Wood Fired Japanese Hot Tub

Acres of nature surround and insulate your moment of rest here at the Laurel Zome. With intriguing geometry drawn directly from the architecture of mountain laurel blossoms, pangolin scales, and pinecones—the simplicity and focus of the zome allows a lofty experience. Wake to natural light spilling in from expansive faceted windows and skylights. Enjoy the ritual of stoking a fire to prime your body to slip into downy sheets for sleep, or into to the waters of your Koto Elements spa tub.

Modern Monteagle A-frame with Hot Tub

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

Maple Yurt Lookout Mountain Chattanooga Glamping

Take advantage of all the activities Lookout Mountain has to offer, from breathtaking hikes and scenic drives to a variety of local attractions. From the Rock City Gardens to the Incline Railway, you’ll find plenty of ways to explore and enjoy the natural beauty of the area. With our yurts, you can relax in comfort and style with all the comforts of home. Enjoy a romantic dinner on the deck overlooking the breathtaking view or just relax and make the most of your time together.

Martin Springs Cabin.

This country cabin is a great base for exploring the nearby South Cumberland Park and surrounding area. Convenient to Sweetons Cove Gulf, The Caverns, Adventure Offroad Park, Sewanee, Monteagle, South Pittsburg/Cornbread Festival, Jasper Highlands. right next to I-24. You can't see any other homes from the cabin and adjacent meadow. Year round creek in the property. Meadow trail. Hot tub and Tuft & Needle mattresses. Basic amenities provided. Includes Wi-Fi and DVD player.

The Coalmont Cabin - Romantic Lakefront Escape

A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

"Near Caverns and Sewanee 2-bedro/2-bath w/EV char

2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped modern kitchen. Easy drive less than 7-mi to Sewanee, and just 10-miles/ 10-12 min to The Caverns. 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/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

CABIN w/ AMAZING VIEWS, HOT TUB, FIRE PIT

Welcome to Monteagle Cabin! Relax, unwind and enjoy the view! Monteagle Cabin has three bedrooms and loft all featuring queen beds, two full bathrooms, kitchen with seating for 10, a fire pit, large deck, a hot tub, and best of all- amazing views! 10 Minutes to South Cumberland State Park 14 Minutes to The University of the South 20 Minutes to The Caverns 30 Minutes to Sweetens Cove Golf Club 50 Minutes to Chattanooga 90 Minutes to Nashville

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH indoor/outdoor CATS*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.

Catch & Release - Spacious Lakefront Getaway

Escape to this bright, spacious 2BR/2BA lakefront retreat—one of the largest homes in the Retreat at Water’s Edge. Sip coffee on the screened porch, kayak or fish from the semi-private dock, and gather by the firepit at sunset. Minutes from world-class hiking, including the nationally acclaimed Fiery Gizzard Trail, yet set on a calm, family-friendly lake perfect for kids to explore and unplug. Ideal for couples, families, or both.

The Sundowner

Come find serenity at The Sundowner where the view drops layers of stress, the sunsets connect you with wonder, and the deer, coyotes, owls, and other denizens reconnect you to nature. The kitchen is well stocked. Fiber internet. Grill, firepit, washer/dryer. 20 min to The Caverns & Fiery Gizzard Trl w Foster Falls; 15 min to Perimeter Trl, Sewanee; 5 to Monteagle. 3bd/2ba includes open master in loft. Toxin free.