Holiday rentals in Sherwood

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Top-rated holiday rentals in Sherwood

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Guest favourite
A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.
Home in South Pittsburg
4.89 out of 5 average rating, 473 reviews

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. New Hot Tub and all new Tuft & Needle mattresses for 2022! Basic amenities provided. Includes Wi-Fi and DVD player.

Top guest favourite
The exterior of the property features a unique sloped roof with a combination of stone and wood materials. Surrounded by greenery, the entrance is approached via a paved path that leads to a welcoming entrance area. Outdoor seating is visible on the balcony, nestled among the trees.
Home in Manchester
4.94 out of 5 average rating, 207 reviews

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

Top guest favourite
An aerial view of Twin Oaks reveals the tiny house surrounded by a winding pathway lined with warm outdoor lights. A cozy fire pit area is set with stone seating, inviting relaxation in the tranquil wooded setting.
Tiny home in Tracy City
4.97 out of 5 average rating, 180 reviews

Twin Oaks tiny house at The Retreat at Waters Edge

Nestled among the oak trees on Monteagle mountain with amazing views of the Fiery Gizzard reservoir, Twin Oaks tiny house is the perfect getaway! Explore the outdoors on hiking trails that lead to waterfalls, see concerts and enjoy eateries, and it's all so easy to get to! Lots of glass that brings the outdoors in if you just want to relax. Each season brings its own unique perspective. Twin Oaks is truly a one-of-a-kind experience. Stay one night or stay a month, you'll love your time here!

Top guest favourite
The exterior of a modern A-frame home features a sleek black façade and a pointed roof. A welcoming front porch is adorned with a planter, while the driveway provides ample parking space. Scenic mountains are visible in the background under a clear blue sky.
Home in Trenton
5 out of 5 average rating, 164 reviews

Mountain's Edge

Mountain's Edge by AAF, built in 2024, is right where you want to be! A cozy, stylish home overlooking the gorgeous views of the valley. While being just far enough away to enjoy the benefits of a quiet mountainous getaway, you're also 25 minutes from downtown Chattanooga, TN, where there is an abundance of amazing activities to partake in! It features a comfortable living space, stunning view with a double decker porch, hot tub, fire pit, and plenty of peace and quiet to relax and enjoy!

Top guest favourite
A well-lit living area features large windows allowing natural light to flood the space. A comfortable brown sofa is complemented by patterned cushions. Glass doors open to a deck, and a small table with decorative items sits nearby.
Tiny home in Tracy City
4.98 out of 5 average rating, 158 reviews

Cozy Tiny Home w/large deck, hot tub and firepit

The Trail House is perfectly placed among the trees with many tall windows to take advantage of the gorgeous views. The large 2-tiered deck has two separate sitting areas. Hike, rock climb, bike, cave, kayak, fish, swim at the base of the waterfalls or sit and relax. Do it all, do absolutely nothing, or a little of both here at the Trail House. There is a second larger home on the same property that can be rented separately listed as New Tiny Home in the Mountains. Shown in last photo.

Guest favourite
A charming cottage is nestled among tall trees in a wooded area. The building features large windows that invite natural light, while a gravel pathway leads to the entrance. Dense greenery surrounds the cottage, creating a tranquil atmosphere.
Tiny home in Monteagle
4.9 out of 5 average rating, 293 reviews

The Nest at The Retreat @ Deer Lick Falls

The Retreat offers a cozy cottage for down time & you have the option to hike trails down to falls area, socialize with other guests or sit and have your own Fire in our fire pit on the property and just relax! Local Restaurants minutes away, lake access 10 minutes away with beautiful woodsy setting perfect for getting away from the hustle of everyday life! Covered patio for relaxing and you can eat outdoors with a grill guests can use and a fully equipped kitchen if you choose to cook.

Top guest favourite
An A-frame cabin is nestled among tall trees, showcasing a modern design with large glass windows. A wooden deck surrounds the entrance, featuring a seating area with chairs and a fire pit. The outdoor area is partially landscaped with natural ground cover.
Cabin in Monteagle
4.98 out of 5 average rating, 124 reviews

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.

Guest favourite
A serene cabin is surrounded by colorful autumn foliage, reflecting beautifully on the calm water. The warm glow from large front windows invites guests to experience the cozy atmosphere inside, while a small dock is visible along the shoreline.
Cabin in Coalmont
4.98 out of 5 average rating, 343 reviews

The Coalmont Cabin – Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

Top guest favourite
The cottage exterior displays a charming entrance with a light blue door framed by a wreath. A cozy seating area is present with two chairs and a small table. A wooden fence adds privacy, and flowering plants are planted along the stone pathway.
Cottage in Village of Pelham
5 out of 5 average rating, 522 reviews

The Milk Barn Cottage

Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about an 8 minute drive away. Pelham has quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

Top guest favourite
A gravel driveway leads to a green cabin nestled among tall trees and vibrant foliage. The surrounding landscape showcases natural greenery, enhancing the cabin's rustic charm. Sunlight filters through the leaves, creating dappled light on the ground.
Cabin in Sewanee
4.96 out of 5 average rating, 290 reviews

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.

Guest favourite
A spacious living area features large windows that let in natural light and provide views of the surrounding trees. A comfortable dark leather sofa is arranged with a rustic wooden coffee table. A wooden rocking chair adds to the cozy atmosphere, beside a staircase made of light-colored wood.
Home in Sewanee
4.9 out of 5 average rating, 194 reviews

Return Guest House and Writers’ Retreat

Welcome to our custom built home on the Cumberland Plateau near Sewanee. This house has been loved by all who visit. The forest setting and the many uniques spaces in the house make it an unforgettable accommodation. Michael shares the property, downstairs on the garden level, unobtrusively. So a host is readily available if you need something.

Top guest favourite
The spacious rooftop deck provides a scenic view of a sunset over rolling hills, framed by trees. A spiral staircase leads to the deck, which is made from wood and offers ample space for relaxation.
Home in Rising Fawn
4.98 out of 5 average rating, 463 reviews

The Cloud 9 Rooftop Deck at On The Rocks Tiny Home

Welcome to Cloud 9 at On The Rocks, a unique repurposed cargo container getaway atop Lookout Mountain, Georgia. The Cloud 9 Rooftop Deck is a true place to relax and meditate, therefore there is no access television. There are 2 shared fire pits located at each end of the property. Firewood is provided along with ingredients to make s'mores.

Popular amenities for Sherwood holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Franklin County
  5. Sherwood