
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.

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)

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.

Twin Oaks tiny house at The Retreat at Waters Edge
Nestled among the oak trees on Monteagle mountain with amazing views of the Fiery Gizzard reservoir, Twin Oaks tiny house is the perfect getaway! Explore the outdoors on hiking trails that lead to waterfalls, see concerts and enjoy eateries, and it's all so easy to get to! Lots of glass that brings the outdoors in if you just want to relax. Each season brings its own unique perspective. Twin Oaks is truly a one-of-a-kind experience. Stay one night or stay a month, you'll love your time here!

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.

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, rock climb, 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 larger home on the same property that can be rented separately listed as New Tiny Home in the Mountains. Shown in last photo.

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks
Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

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).

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*

the tiny bungalow @ waters edge | tiny house
welcome to our favorite little bungalow. located in tracy city, tn @ the waters edge tiny house community. cozied in the woods, we love to host our guest not just with a retreat but an experience. we have deigned our place to have what you need, so you can show up and rest. our tiny bungalow is perfectly designed for that romantic getaway, a writers retreat, an escape for friends to connect over an open fire, or a family adventure hiking the trails + paddling out on the lake.

Dock on Lake! Walk to Downtown Shops/Rest/Movies!
Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

"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.
Popular amenities for outdoor seating rentals in Winchester
House rentals with outdoor seating

Sunset Cottage +Dock on Tims Ford Sleeps 12

Little Green Cottage

Meadow View Retreat

Nanny’s House

Basecamp Retreat TimsFordLake

Lakeside Paradise - Waterfront View & Private Dock

Return Guest House and Writers’ Retreat

Relax & Unwind in Cozy Farm Stay 7 mins from I-24
Apartment rentals with outdoor seating

Boho Hideaway

The Yurt at Paradise Pointe with a hot tub, fire p

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

Beautiful New Construction Lakefront!

Whitetail Creek Lodge Close to Campus

Serene Lake House Retreat with New Golf Cart

Restful Modern Tiny House Nestled into the Plateau

The Modern Mainstay at Barefoot Bay

Tims Ford *FreeUTV/kayaks/canoe*2.5 acres/private

5 Acres! Cozy Nature Retreat

A quiet getaway.
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $304 SGD | $279 SGD | $352 SGD | $335 SGD | $407 SGD | $434 SGD | $424 SGD | $419 SGD | $331 SGD | $350 SGD | $363 SGD | $322 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 $39 SGD per night before taxes and fees

Verified guest reviews
Over 2,560 verified reviews to help you choose

Family-friendly holiday rentals
80 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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- Rentals with lake access Winchester
- Cabin rentals Winchester
- Rentals with a kayak Winchester
- Rentals with a firepit Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with a fireplace Winchester
- Pet-friendly rentals Winchester
- Rentals with a patio Winchester
- Rentals with pools Winchester
- Family-friendly rentals Winchester
- House rentals 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
- Dublin Park
- Rock City
- Coolidge Park
- Chattanooga Choo Choo
- Hunter Museum of American Art
- Creative Discovery Museum
- Von Braun Center, North Hall
- South Cumberland State Park
- Tims Ford State Park
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Burritt on the Mountain
- Point Park
- Raccoon Mountain Caverns & Campground
- Finley Stadium
- Chattanooga Whiskey Experimental Distillery
- Chattanooga Zoo
- Cathedral Caverns State Park
- Jack Daniel's Distillery
- Old Stone Fort State Archaeological Park




