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.

%{current} / %{total}1 / 1
Top guest favourite
A rustic cabin is situated on a lush green lawn, surrounded by tall trees. The two-story structure features a spacious deck with wooden railings, and steps that lead to the entrance. Play equipment is positioned nearby, enhancing the outdoor space.
Cabin in Lancing
4.93 out of 5 average rating, 120 reviews

Lilly Bluff Cabin Getaway

This beautiful cabin nestled in the heart of East Tennessee offers incredible access to the Obed Wild & Scenic River and surrounding areas. With all the amenities you need and a breathtaking view, this cabin won't disappoint! Lilly Bluff Cabin is ideally located for outdoor adventure or a quiet private getaway. If you're looking for outdoor adventure Lilly Bluff cabin is in close proximity to canoeing, kayaking, rock climbing or hiking. Come explore the natural beauty of the Tennessee mountains!

Top guest favourite
A newly built treehouse is perched among trees on a forested property. It features large windows, a covered deck with a railing, and sturdy wooden support beams. The surrounding greenery enhances the natural setting, offering a sense of seclusion and tranquility.
Treehouse in Spring City
5 out of 5 average rating, 114 reviews

Spring City Treehouses

This is a unique, newly built Treehouse (‘23) on 10 wooded acres near Watts Bar Lake. Nearby marinas, restaurants, hiking, waterfalls & a short drive to whitewater rafting & Gatlinburg! Enjoy the peace & quiet of your private deck overlooking a small Holly grove, lush forest & seasonal creek! Fire pit w/ sitting area, outdoor kitchen & BBQ. Comfy space upstairs w/queen memory foam bed, futon loveseat, full bath, fireplace & mini kitchen. Free kayaks to use at own risk. No pets or kids under 12!

Guest favourite
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, 136 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 favourite
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 homes in Crossville
4.98 out of 5 average rating, 179 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 favourite
A modern cabin is nestled among tall trees, showcasing large windows that reflect the warm glow of interior lighting. The exterior deck extends towards the lush greenery, providing a seamless connection to the surrounding nature. Hills are visible in the background, enhancing the serene atmosphere.
Cabin in Sparta
4.98 out of 5 average rating, 108 reviews

Big Bottom Bungalow: Park Views, Secluded, Hot Tub

You can soak in tranquility at this modern cabin with a hot tub, indoor fireplace and outdoor living space. The Caney Fork River borders the 63 acre farm, which connects directly to over 60,000 acres of protected wilderness where you have free access to miles of hiking trails, magical waterfalls, historic homesteads and impressive caves. At the cabin, you can listen to the sounds of nature as you take in the scenic valley views of Big Bottom and the mountain views of Scott’s Gulf State Park.

Top guest favourite
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 homes in Pikeville
4.99 out of 5 average rating, 338 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 favourite
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, 169 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.

Top guest favourite
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, 153 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...

Guest favourite
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, 103 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 favourite
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 homes in Crossville
4.97 out of 5 average rating, 157 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 favourite
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, 144 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.*

Top guest favourite
The charming farmhouse exterior features a stone facade, gabled roof, and welcoming front porch. A well-maintained yard with green grass and a large tree provides shade. A paved driveway leads to the entrance, while the scenic countryside is visible in the background.
Home in Crossville
5 out of 5 average rating, 127 reviews

Charming Historic Farmhouse

Relax in a beautiful and historic farmhouse located in the Cumberland Homesteads Historic District. The 1800 square foot home is situated on working cattle and hay producing farm. It is surrounded by countryside consisting of neighboring small farms with rolling pastures and a mountain view. Unwind and enjoy a bit of history in a scenic rural setting. The 2026 calving season begins in March.

Popular amenities for vacation rentals near Chestnut Hill Winery