Places to stay near Chestnut Hill Winery

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Top-rated vacation rentals near Chestnut Hill Winery

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Top guest favorite
An inviting structure resembling a general store features wooden siding and a covered porch. Rustic benches and log seating circle a gravel area, with trees providing shade. Vintage signage and decor enhance the entrance, which is framed by natural greenery.
Cabin in Monterey
4.98 out of 5 average rating, 536 reviews

Little Cabin in the Woods

Bring your Kayak and enjoy the Mtn air in the comfort of our little Cabin on 5 wooded acres with a private Lake. Listen to the coyote's howl, campfires burn bright, and night sky's brindle with the twinkle of distant stars and fireflies. Daytime, pull on your hiking boots and enjoy the nearby state parks, lakes, and waterfalls. Just 3.5 miles off I-40, bounce in town or down the mtn for the perfect meal. Zipline, paddleboat, campfires & memories abound! Hosts live on property/avail 24/7.

Guest favorite
A log cabin with a green metal roof is surrounded by trees, featuring a welcoming front porch with rocking chairs. Soft light glows from the windows, inviting guests to explore the tranquil setting. A gravel pathway leads to the entrance, enhancing the natural ambiance.
Cabin in Crossville
4.9 out of 5 average rating, 138 reviews

Secluded Log Cabin 1 mi from Cumb Mtn State Park

Keep it simple at this peaceful and centrally-located genuine log cabin, once featured in Log Cabin Homes and Log Home Living. This beautiful log home creates a calm space by avoiding overhead lighting on the main floor. The window placement and lamps provide more than enough light without taking away from the natural aesthetic. Master bedroom has a tv, KNG bed, & a private bath with walk-in shower. 2nd FL has a QN bed, 3 TWN beds and full bathroom. *2 add’l TWN beds avail upon request.

Top guest favorite
A serene cottage stands next to a clear, turquoise pond, surrounded by lush greenery. The building features a light exterior with large windows. Two chairs are positioned near the water's edge, inviting relaxation and enjoyment of the natural surroundings.
Tiny home in Crossville
4.98 out of 5 average rating, 186 reviews

Nanny’s Cottage

Conveniently close to Fairfield Glade Golf courses, and other activities. Nanny’s Cottage is 300sqft with 1 full bed room w/ queen bed, full bath, washer and dryer, and WiFi. It has big picturesque windows for lots of natural lighting, but also blackout blinds to darken the inside. The outside of the property boasts a beautiful pond and dock to have a relaxing place to sit and enjoy the sunshine and fresh air. To enjoy the outside on those chilly nights we have a fire pit with outdoor sitting.

Top guest favorite
A rustic cabin is framed by autumn foliage, featuring wooden siding and a welcoming sign. A small porch extends from the front, supported by wooden beams. A stone fire pit is visible in the foreground, alongside a single black chair resting on the ground covered in fallen leaves.
Cabin in Jamestown
4.93 out of 5 average rating, 175 reviews

River cabin on waterfalls BRING YOUR PETS!

Beautiful OFF GRID pet friendly cabin located on the Clearfork River. Over a mile of secluded river frontage and 4 SEASONAL waterfalls. Huge bluffs to explore. Large gated deck with picnic table and gas grill. Great place for you and your furry friends to hang out. This is OFF GRID, OFF ROAD, needing off road capable vehicle and adveturous outdoors loving people. This is not a cabin to send grandma in the Camary. {PLEASE READ ALL INFORMATION AND PHOTOS} Totally away from society!!

Top guest favorite
An expansive wraparound deck features a dining table surrounded by chairs, with a stunning view of the mountains and a sunset in the background. The area is illuminated by string lights, highlighting the outdoor space's inviting atmosphere.
Tiny home in Pikeville
4.99 out of 5 average rating, 346 reviews

Romantic cliffside bungalow with amazing views

Perched on the side of a cliff with a spectacular view of the mountains of the Cumberland Plateau and Sequatchie Valley, Cliffside is a unique contemporary Scandinavian-style property. Whether you're on vacation or working remotely, enjoy coffee in front of the large picture windows, a soak in the hot tub, sunset on the large deck, a chat around the smokeless firepit, or kayaking on the nearby lake. Located on Dayton Mountain near many hiking trails, it is only a 20-minute drive to Dayton.

Top guest favorite
The exterior of a log home is shown, featuring a white door and a stone pathway leading to it. The rustic wooden siding highlights the natural textures. Surrounding greenery and trees frame the entrance, providing an inviting view of the property.
Farm stay in Lancing
4.96 out of 5 average rating, 171 reviews

Bunkroom at Fiat Farm

Tuck yourself into this cozy bunkroom attached to a custom-built log home. Situated on the site of a hundred-year-old homestead, this 67-acre property is now a regenerative farm. 10 minutes from Lilly Bluff overlook with hiking and rock climbing. A short drive to many Obed trailheads. Only 30 minutes to Frozen Head State Park. This space will be the basecamp for all your adventures. Or just enjoy the solitude as you explore the property and visit our farm animals. Welcome to Fiat Farm.

Guest favorite
A ranch-style brick home is depicted with a covered front porch featuring seating arrangements. Decorative plants are positioned at the entrance, and the lawn is well-maintained, adding to the home's appeal. A clear sky and sunlight create a serene atmosphere.
Home in Crossville
4.92 out of 5 average rating, 185 reviews

The Restful Retreat

This beautiful ranch style brick home sits on 24 acres of mostly wooded property. From the front porch you have a wonderful view of Hinch Mountain. There are 3 beds and 2 baths with a large open kitchen and dining room. There is a laundry room with washer and dryer and additional playroom and mud room. There is an additional outdoor space converted from an old barn into a hangout space with a porch swing, dining table, string lights, grill, and extra seating. A fantastic place to relax!

Top guest favorite
The cabin's entrance is highlighted by a welcoming front porch adorned with rocking chairs and potted yellow mums. A decorative wreath hangs on the door, while soft outdoor lighting enhances the space. The surrounding area features lush green grass and trees, visible in the background.
Cabin in Crossville
5 out of 5 average rating, 100 reviews

Cozy Country Cabin

We welcome you to our country cabin, a wonderful place for a couple’s getaway or quiet corner all to yourself. Enjoy the clean, country air and starry night skies away from city lights; on a quiet, low traffic road facing woods and farmland with field, pond, and forest behind. We are just across the field from a working dairy farm and less than a mile from the dairy farm store and creamery where you can find fresh meat, eggs, milk, and some of the country’s best hand-dipped ice cream!

Top guest favorite
The entrance features a handcrafted wooden door framed by natural stone, showcasing intricate carvings. Outside, a stone pathway leads to a seating area with metal chairs and a table, overlooking expansive valley views under a clear sky.
Home in Spring City
4.99 out of 5 average rating, 162 reviews

Handsculpted Nature Inspired Enchanting Horizons®

Come create memories at Enchanting Horizons®. Stay in a unique hand-sculpted story-book cottage with panoramic mountain and valley views. Take a break from the routine, and come to this creative space built to inspire adventure, promote relaxation and spark romance. Explore the worlds 2nd largest underground lake, Scuba dive with dinosaurs, fly tandem in a paraglider, go waterfall hunting, play golf in "the golf capital of Tennessee" and more...

Top guest favorite
A charming yellow farmhouse is nestled in a lush green landscape, flanked by mature trees. The sky is bright with scattered clouds, and sunlight filters through the leaves, casting a pattern on the grassy area in the foreground.
Home in Crossville
4.95 out of 5 average rating, 106 reviews

Dalton Farm-quiet, country setting w/ fishing pond

Welcome to the Dalton Farm! Located 1.5 miles from Peavine Road exit off of I-40 and 7 miles from Fairfield Glade Golf Resort in Crossville. Farm is very private and has been in the family for 50 years. Guests will have access to a pool room, laundry room, full size kitchen and fully stocked fishing pond (no swimming)! Near to many local restaurants, antique shops, hiking and golfing communites! Property is perfect for your next family getaway!

Top guest favorite
The elevated cabin features a wooden exterior nestled among trees, illuminated warmly from within. Large windows provide glimpses of the interior and surrounding natural landscape. Stone steps lead to the cabin entrance, enhancing its rustic charm.
Tiny home in Crossville
4.97 out of 5 average rating, 165 reviews

Cozy elevated cabin nestled in the woods.

This glass and wood elevated cabin sits beneath giant Oak trees and above mossy boulders. The small single room does not have a bathroom or kitchen. A common area with an outdoor kitchen and bathhouse is less than a minute walk away. The approximately 250 square foot cabin has Oak hard wood floors, ceiling fan, mini fridge and Bluetooth speaker. It is well insulated and stays comfortable even in mid summer without AC.

Guest favorite
A welcoming front porch features wooden posts supporting an overhang. American and Tennessee flags are displayed on either side, while potted plants add a touch of greenery. The pathway leads to a pair of double doors set within a beige exterior and surrounded by grass.
Home in Crossville
4.95 out of 5 average rating, 150 reviews

Downtown Crossville home, close to I-40

This three-bedroom home is located in the downtown area of Crossville. This property is perfect for exploring, passing through, or just relaxing. Interiors and furnishings are new, comfortable, and plentiful. You'll be close to the many golf courses, parks, and hiking trails in Cumberland County, in addition to the quaint downtown shops and attractions. *Please note this area is downtown where traffic can be heard.*

Popular amenities for vacation rentals near Chestnut Hill Winery