Winchester Vacation Rentals

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Vacation Rentals in Winchester

S'mores & More Tiny House - Tracy City

Tracy City TN

$281 nightly

$329 total

Dec 18 - Dec 19

Total with taxes and fees

Located in Tracy City, this vacation home is a 4-minute drive from Fiery Gizzard Grundy Forest Trailhead and 5 minutes from South Cumberland State Park.

Kitchen

Washer

Mountain Point of View Cottage - 15 Minutes from the Caverns!

Pelham TN

$169 nightly

$193 total

Jan 15 - Jan 16, 2026

Total with taxes and fees

Located in Pelham, this vacation home is in the mountains, within a 15-minute drive of Elk River and Monteagle Sunday School Assembly.

Kitchen

Pet friendly

Robert's Manor - A Historical Home from 1880s

tracy city TN

$593 nightly

$593 total

Jan 15 - Jan 16, 2026

Total with taxes and fees

Located in Tracy City, this vacation home is in the mountains, a 3-minute drive from Fiery Gizzard Grundy Forest Trailhead and 5 minutes from South Cumberland State Park.

Kitchen

Barbecue grill

Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall

Monteagle TN

$215 nightly

$242 total

Dec 18 - Dec 19

Total with taxes and fees

Located in Monteagle, this vacation home is within a 15-minute drive of South Cumberland State Park and Bigfoot Adventure TN Zipline.

Kitchen

Washer

Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

Sewanee TN

Located in Sewanee, this vacation home is in a rural location, within a 15-minute walk of University of the South and Lake Finney.

Kitchen

Washer

Caverns,Sewanee,Waterfalls,Fall Hike:Tiny Basecamp

Monteagle TN

$201 nightly

$201 total

Dec 18 - Dec 19

Total with taxes and fees

Located in Monteagle, this vacation home is in the mountains, within a 5-minute drive of South Cumberland State Park and Harton Park.

Kitchen

Washer

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

Monteagle TN

$292 nightly

$328 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

Located in Monteagle, this vacation home is on a river, within a 15-minute drive of South Cumberland State Park and Bigfoot Adventure TN Zipline.

Kitchen

Washer

Mountain Memories to provide a cozy retreat on your vacation!

Monteagle TN

$185 nightly

$209 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

With a stay at this vacation home in Monteagle, you'll be within a 5-minute drive of Harton Park and Monteagle Sunday School Assembly.

Kitchen

Washer

Beautiful Monteagle Bluff Mountain Home Sleeps 12

Monteagle TN

Located in Monteagle, this vacation home is in the mountains, within a 10-minute drive of Harton Park and South Cumberland State Park.

Kitchen

Washer

Cumberland Forest Cottage - Quiet & Sizable Back Yard!

Monteagle TN

$204 nightly

$204 total

Jan 15 - Jan 16, 2026

Total with taxes and fees

When you stay at this vacation home in Monteagle, you'll be in the mountains, within a 5-minute drive of Harton Park and Monteagle Sunday School Assembly.

Kitchen

Air conditioning

3-Br Luxury Home with Hot Tub & Arcade Games

Tracy City TN

Located in Tracy City, this vacation home is on a lake, a 3-minute drive from Fiery Gizzard Grundy Forest Trailhead and 6 minutes from South Cumberland State Park.

Hot Tub

Kitchen

Kayak Kove* DOCK* Lake front Tim's Ford Lake NEW- 2 kayaks

Winchester TN

With a stay at this vacation home in Winchester, you'll be on a lake, just a 2-minute walk from Tims Ford Lake and 11 minutes by foot from Expressions.

Washer

Dryer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.