
Holiday rentals in Sherwood
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Top-rated holiday rentals in Sherwood
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Luxury tiny cottage with deck hammock and hot tub!
Welcome to the beautiful Highland Cottages at Lake Guntersville! Each cottage has a built-in King bed with memory foam mattress, a kitchenette with a coffee maker, tea kettle, dishes, glasses, and cutlery, and even a small refrigerator. Pamper yourself at the beautiful vanity with all the items needed to make you look and feel your best. Included are a hair dryer, makeup mirror, complimentary soaps and lotions, and the softest towels we could find. The deck and hot tub complete the experience!

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.

The Coalmont Cove - Romantic Lakefront Escape
The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. The Coalmont Cove is a tiny home that sits in the cove of a private lake. The definition of relaxation with adventure only minutes away, you'll find elevated decor, an inviting outdoor space, and beautiful scenery. The perfect retreat if you’re looking for a romantic getaway or a quiet place to disconnect or work remotely (1 GB fiber optic internet).

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.

"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.

Cabin 222: the best in comfort, location, & value
Cabin 222 was a tiny house before they were cool! This small single room accommodation has a queen bed, wifi, roku tv, small refrigerator, microwave, coffee maker, and full bath. 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.

Scandinavian Treetop Bliss @ Terralodge
Soar into our Scandinavian treehouse on Monteagle’s "bio-gem"! Luxuriate in king beds, a hot tub, and smokeless firepit. Swim or fish in the shared pond, hike to our cave, or play lawn games. With fiber WiFi, 4K TV, and full kitchen, it’s perfect for work or play. Near Monteagle (7 min), Sewanee (15), The Caverns (25), plus epic hikes and lakes. Chattanooga (45 min), Nashville (90). Book this luxe treetop escape!
Popular amenities for Sherwood holiday rentals
Other great holiday rentals in Sherwood

Spring Sewanee Lakehouse

Endless View - Crisp & Cozy Lower Cottage

Haven Forest House

"A Modern Vue"-Luxury-Hot Tub-Arcade

Forest Retreat: Poolside Bliss Close to Campus

Lakefront Tiny Home/Pet Friendly/ Private Dock

Nature lovers dream retreat/the Square Root

Fully remodeled cabin, next to Walls of Jericho
Destinations to explore
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Lake Winnepesaukah Amusement Park
- Coolidge Park
- Chattanooga Choo Choo
- Hamilton Place
- Rock City
- Hunter Museum of American Art
- Point Park
- South Cumberland State Park
- Chattanooga Zoo
- Creative Discovery Museum
- Old Stone Fort State Archaeological Park
- Raccoon Mountain Caverns & Campground
- Chickamauga Battlefield Visitor Center
- Lowe Mill Arts And Entertainment
- Von Braun Center, North Hall
- Cathedral Caverns State Park
- Huntsville Botanical Garden
- Tennessee Valley Railroad Museum
- U.S. Space & Rocket Center
- Cumberland Caverns
- Burritt on the Mountain





