Holiday rentals in Sherwood

Whippoorwill Retreat Treehouse

“Escape, 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.

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.

Window Rock | Jackson Point · Modern Bluff Retreat

A design-led retreat on 7 private acres above the valley. Two bedrooms, 2.5 baths, panoramic views. Near Sewanee on Tennessee's Cumberland Plateau — close to MICHELIN-recognized dining, world-class hiking, and some of the darkest skies in the Southeast. Soak in the cedar tub. Put a record on the vinyl station. Sit on the deck at sunset and forget to check your phone. See more images and videos on our socials: @windowrockmodern and don't forget to check out our sister property, The A-Frame.

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.

Stayframe: a designer getaway with mountain views

Welcome to my custom-built Aframe in the forest just 90 mins from Nashville. This quiet retreat perched on the Cumberland Plateau was recently featured in Travel + Leisure and gives you access to the hikes and waterfalls the area is known for, while offering an elevated experience. Enjoy the soaking tub, gas fireplace, fast wifi, Smart TV, well-appointed kitchen, and bluff views. Sewanee University, Cumberland Caverns, Fiery Gizzard, and Sweetens Cove are all within a short drive.

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.

Creekside Nook in Sewanee

Get ready to relax in this 3-bedroom new built house in Sewanee. The space features a king bed, a queen bed, and fun bunk beds perfect for families or groups. With two bathrooms, getting ready is easy and convenient. A full kitchen offers ease with basic cooking needs. Whether you’re winding down after a day of exploring or enjoying a quiet morning, this terrific home offers a welcoming atmosphere. Fall in love with Sewanee and enjoy the magic it has to offer.

"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.

Waterfront Access | Lake Views | Dock | Pool Table

Indulge yourself with private waterfront access and stunning million dollar views in this sunny slice of paradise. Experience our waterfront lounge, on-site boat dock, outdoor fireplace, pool table, mini golf putting green, tiki lamps, luxurious jacuzzi tub with spa jets, outdoor dining, sleepy sunroom, charcoal grill, 4K smart TV's, and fully inspired gourmet chef's kitchen. Welcome to "Lakeside Paradise."

Cabin 111 - the best in location and comfort!

Cabin 111 has a queen bed, wifi, roku tv, small refrigerator, microwave, coffee maker, and full bath. A deck off the back gives additional space for relaxing. SUPER close to the campus of the University of the South and downtown Sewanee. Enjoy privacy while having access to most things within a short walk. Hiking trails, restaurants, campus! Or just enjoy the nature and deer from the side patio.

Airstream #97 at The Grove

Sleep in a vintage 1997 Airstream! Fully updated with modern comforts, #97 is nestled in our forest campground, the perfect spot for your laid back Mountain getaway. The Grove at Natural Bridge features 3 vintage Airstreams, a shared well appointed bathhouse and restrooms. Located just a short drive (2.2 miles) from The University of the South and walking distance to Natural Bridge State Park.