
Places to stay near Chestnut Hill Winery
Book unique vacation rentals, homes, and more on Airbnb
Top-rated vacation rentals near Chestnut Hill Winery
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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.

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!!

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.

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.

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!

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!

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...

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!

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.

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
Condo rentals with wifi

Fairfield Glade 1BR Dlx w/ Full Kitchen

Cozy Lakefront 4 bedroom condo w/indoor fireplace

Gem in the heart of Fairfield Glade

Cozy Country Club Condo

★Cozy 2B/1.5B ♥ of Fairfield Glade -KING BED, WIFI

14 Wilshire Retreat

Lovely 2-bedroom condo

Clean and convenient condo on 10th
Family-friendly house rentals

Cabin-Inspired Studio

Cabin by Bear Lake

Townside Nook | Downtown Sparta's Retro Retreat

New Modern Luxury Mountain Cottage

Hilltop Haven- Lakefront Private Walkout Apartment

Spacious 3BR home for your adventure getaway.

Welcome to the Old Farmhouse. 3 bedroom house.

BY FAIRFIELD GLADE ♥️ THE COUNTRY OASIS!🥂❤🥂
Apartment rentals with air conditioning

Comfy Retreat - 2 min to town

Dixie Lee Bed & Barn

Private Modern Apartment

Beach House

Big Bass Lake Rental

Big city loft with small town charm

Stay & Play GetAway- Suite A Cumberland Place

A Fixer-Upper Style Place
Other great vacation rentals near Chestnut Hill Winery

Luxury Cottage Escape Near Fall Creek Falls Park

Hannsz Hideaway

Big Bottom Bungalow: Park Views, Secluded, Hot Tub

Watermore Cottage

Original Cabin w/Fast Wi-Fi. Fire Pit. 10 to Town

Lilly Bluff Cabin Getaway

The Water’s Edge at Whites Creek

Cabin by the Creek




