
Vacation rentals with outdoor seating in Winchester
Find and book unique outdoor seating rentals on Airbnb
Quick stats about vacation rentals with outdoor seating in Winchester

Total vacation rentals
Explore 80 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$2,093 GYD per night before taxes and fees

Verified guest reviews
Over 2,710 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Winchester vacation rentals include wi-fi 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!
Top-rated outdoor seating rentals in Winchester
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Private Dock - Best Cabin Tims Ford Lake
Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

Private dock/gazebo on quiet cove. Tims Ford Lake!
Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

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.

Lakeside Retreat at The Reserve w/ Golf Cart
Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

2BR Nature Getaway in Tiny Home w/ Lake access
Nature's Nook is a charming two-bedroom cottage. Combining nature with cutting-edge design draws inspiration from all over. Providing a fairytale experience with a cozy interior amidst towering trees. Nature's Nook embraces the beauty of nature with the inside scent of a campfire-lit night to birds singing good morning. This provides the ideal getaway to relax but still includes hiking and adventure. Nature is calling you at the Nook. . . Follow us on our socials @NaturesNookTN

VACATION CABIN - Sunday Morning Rentals
We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

The Coalmont Cabin - Romantic Lakefront Escape
A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

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.

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

Lovely Lake View Home at Twin Creeks Marina
This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Catch & Release - Spacious Lakefront Getaway
Escape to this bright, spacious 2BR/2BA lakefront retreat—one of the largest homes in the Retreat at Water’s Edge. Sip coffee on the screened porch, kayak or fish from the semi-private dock, and gather by the firepit at sunset. Minutes from world-class hiking, including the nationally acclaimed Fiery Gizzard Trail, yet set on a calm, family-friendly lake perfect for kids to explore and unplug. Ideal for couples, families, or both.

Scandinavian Treetop Bliss @ Terralodge
Soar into our Scandinavian treehouse on Monteagle’s "bio-gem"! Luxuriate in king beds, a hot tub, and smokeless firepit. Swim or fish in the shared pond, hike to our cave, or play lawn games. With fiber WiFi, 4K TV, and full kitchen, it’s perfect for work or play. Near Monteagle (7 min), Sewanee (15), The Caverns (25), plus epic hikes and lakes. Chattanooga (45 min), Nashville (90). Book this luxe treetop escape!
Popular amenities for Winchester outdoor seating rentals
House rentals with outdoor seating

Sunset Cottage +Dock on Tims Ford Sleeps 12

The Hangout on Heath Lane

Lakeside Luxe | Lake + Pool Access

Meadow View Retreat

Basecamp Retreat TimsFordLake

Lakeside Manor Retreat

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Chalet 638 - state park, golf & The Caverns
Apartment rentals with outdoor seating

Boho Hideaway

The Snuggle Bus Skoolie

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

Mountain Retreat Overlook 7 min walk to Caverns
Other vacation rentals with outdoor seating

TC Easy Breeezee

Serene Lake House Retreat with New Golf Cart

Barefoot Dreams

Waterfront Cottage #7 - PET Friendly & Free Boat!

Lakeshore Modern- steps to water

Tennessee Barrel House

Lakefront Lodge

Cottage on Cedar
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$45,425 GYD | G$42,285 GYD | G$50,030 GYD | G$54,426 GYD | G$66,148 GYD | G$70,544 GYD | G$68,870 GYD | G$68,032 GYD | G$53,798 GYD | G$51,914 GYD | G$54,217 GYD | G$41,657 GYD |
| 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 |
Destinations to explore
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- Rentals with lake access Winchester
- Rentals with a fire pit Winchester
- Cabin rentals Winchester
- Rentals with a kayak Winchester
- Rentals with a washer and dryer Winchester
- Pet-friendly rentals Winchester
- Family-friendly rentals Winchester
- Rentals with a fireplace Winchester
- House rentals Winchester
- Rentals with pools Winchester
- Rentals with a patio 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
- Rock City
- Chattanooga Choo Choo
- Coolidge Park
- South Cumberland State Park
- Point Park
- Hunter Museum of American Art
- Von Braun Center, North Hall
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- Old Stone Fort State Archaeological Park
- Creative Discovery Museum
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Cumberland Caverns
- Cathedral Caverns State Park
- Short Mountain Distillery
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Barfield Crescent Park





