Holiday rentals in Sherwood

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm from the peaceful, serene back yard. We have a 72 acre farm and a family business located walking distance from the airbnb where you can grab a coffee, a bite to eat + stroll around the greenhouses! This 2 BDR house is the perfect stay for families, couples getaway or business trips. Conveniently located in Winchester, a short drive to the beautiful historic downtown Winchester, Tim’s ford Lake and Sewanee University.

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.

Forest Retreat: Poolside Bliss Close to Campus

Welcome to your spring getaway in Sewanee. This inviting 3-bedroom home offers spacious living areas, serene outdoor spaces, and a convenient location near the University of the South. Walk to campus events, local restaurants, and nearby scenic trails while enjoying the fresh mountain air and blooming landscapes of the season. Whether you’re visiting family, exploring the Domain, or planning a peaceful weekend retreat, this comfortable home provides the perfect place to relax and recharge.

Whitetail Creek Lodge Close to Campus

Escape to Sewanee this spring at a private 34-acre mountain retreat just minutes from campus. Surrounded by peaceful forest scenery, this redesigned home offers expansive covered patios, a private pond dock, and inviting outdoor spaces perfect for relaxing in the fresh mountain air. Gather around the outdoor fireplace after days spent exploring campus events and nearby trails. With spacious accommodations and comfortable amenities throughout, this retreat is ideal for seasonal getaways.

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.

Cozy Bluff View Cabin w/ Hot tub in Monteagle

Welcome to "In The Pines", a charming bluff-view cabin nestled in the heart of Monteagle, TN! Whether you're seeking a peaceful retreat, catching a show at The Caverns, or exploring the scenic trails of South Cumberland State Park, this is the perfect getaway. Relax and unwind with family and friends in this cozy mountain escape, featuring 3 bedrooms, 2 full bathrooms, and a loft with a full-size fold-out futon. Enjoy breathtaking bluff views from the patio or soak in the jacuzzi!

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.

Long Weekend

Tranquility and beauty surround this home located on campus and close to The Cross. Long Weekend can comfortably house 10 people. The main floor has one bedroom and bathroom, a full eat -in kitchen with new dishwasher, a cozy den with fireplace, a dining room, two porches, and a garage. Upstairs are 3 more bedrooms and two full baths. Enjoy hiking, cooking, Sewanee events, or just gazing out the windows over the pond. We hope you enjoy our family home as much as we do.

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.

Sewanee Mountain Lake House

Escape to the natural beauty of Sewanee this spring at a secluded lakefront retreat set on 30 wooded acres. Featuring updated interiors, peaceful surroundings, and private hiking trails, the home offers a relaxing setting for outdoor enthusiasts. Explore forest paths, enjoy views of the hidden lake below the dam, or simply unwind in the quiet atmosphere of the South Cumberland Plateau just minutes from the University of the South.

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."