
Holiday rentals with outdoor seating in Winchester
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Top-rated rentals with outdoor seating in Winchester
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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.

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.

Waterfall Log Cabin
Cozy Log Cabin just feet away from the top of our 2 magnificent private waterfalls. The Falls at Sewanee Creek is located in America’s most biodiverse area on Tennessee's Eco-Rich Cumberland Plateau. Walk to the observation bench at the top of the biggest 50 ft waterfall. Follow the trail behind the falls. Adventure awaits on a rugged, bouldering hike, past cascades and the second big waterfall to two private caves. Disclaimer: Flow of all Waterfalls is subject to weather fluctuations.

Tennessee’s ONLY Luxury Safari Tent Getaway
Soak in sweeping mountain and valley views from your private hot tub at this remote, luxury safari tent. Unwind on a plush king bed, sip wine beside the glowing fire feature, and bask in unforgettable sunrises and sunsets. Surrounded by nature, peace, and starry skies, this hidden gem is the perfect escape. Just minutes from waterfalls and hiking, it’s glamping at its most magical—serene, stylish, and tucked far away from it all. Reconnect with what matters: nature, stillness, and yourself.

Holliday Hide Away
1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

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.

The Coalmont Cove - Romantic Lakefront Escape
The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. The Coalmont Cove is a tiny home that sits in the cove of a private lake. The definition of relaxation with adventure only minutes away, you'll find elevated decor, an inviting outdoor space, and beautiful scenery. The perfect retreat if you’re looking for a romantic getaway or a quiet place to disconnect or work remotely (1 GB fiber optic internet).

Mac's Lodge Tiny Home
FEATURES A HOT TUB! Relax in style at Mac's Lodge (formerly listed as The Seashore), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

"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/ YouTube TV and streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Cozy Cabin close to Tims Ford Lake & Jack Daniels
A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

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, 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 home on the same property you can rent listed as New Tiny Home in the Mountains. See the last picture.

Owl’s Nest Treehouse Getaway w/ Hot Tub & Fire Pit
Reconnect with nature at this unforgettable treehouse escape. One of the few treehouse cabins in Tracy City, located on 2 acres of beautiful wooded land. We are less than 1 mile from South Cumberland State Park with access to hiking trails, creeks, and Mountain views. Enjoy the sounds of the woods on our elevated deck, or relax in the private hot tub down below. The newly renovated outdoor space includes a grill, fire pit, pond & hanging egg chairs.
Popular amenities for outdoor seating rentals in Winchester
House rentals with outdoor seating

The Hangout on Heath Lane

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

Little Green Cottage

Meadow View Retreat

Sisters Point Cabin

3-BR Luxury Home with Hot Tub & Arcade Games

Relax & Unwind in Cozy Farm Stay 7 mins from I-24

The FOX Tiny Home @ The Retreat at Water's Edge
Apartment rentals with outdoor seating

Boho Hideaway

Cozy and Adorable

TN Honey new construction two bedroom apartment

Cozy Up in Monteagle

Newly Renovated Cozy Place Minutes From The Lake

Russell and Beckys place

Adorable & Stylish Studio in Monteagle, TN!

Goat Pen Hostel - Overlook
Other holiday rentals with outdoor seating

Lakeside Retreat at The Reserve w/ Golf Cart

Sunset Cottage +Dock on Tims Ford Sleeps 12

Granny's Guest House

The Lakefront Getaway! Pool, Fire Pit, Marina!

Barefoot Dreams Waterfront w/Flat Lot, Pool, SUPs

Whitetail Creek Lodge Close to Campus

Serene Lake House Retreat with New Golf Cart

Waterfront Cottage #7 - "Dog Daze" PET friendly!
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $309 SGD | $284 SGD | $357 SGD | $340 SGD | $413 SGD | $441 SGD | $430 SGD | $425 SGD | $336 SGD | $356 SGD | $369 SGD | $327 SGD |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
Quick stats about holiday rentals with outdoor seating in Winchester

Total holiday rentals
Explore 80 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 2,510 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
80 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Winchester
- Rentals with lake access Winchester
- Rentals with a firepit Winchester
- Cabin rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a kayak Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with a fireplace Winchester
- House rentals Winchester
- Rentals with a patio Winchester
- Rentals with pools Winchester
- Rentals with outdoor seating Franklin County
- Rentals with outdoor seating Tennessee
- Rentals with outdoor seating United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- The Ledges
- Coolidge Park
- Chattanooga Golf and Country Club
- Chattanooga Choo Choo
- Old Fort Golf Course
- Hunter Museum of American Art
- Creative Discovery Museum
- National Medal of Honor Heritage Center
- Kyujo-mae Station




