Winchester Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Winchester hotels

Vacation Rentals in Winchester

S'mores & More Tiny House - Tracy City

Tracy City TN

$300 nightly

$352 total

Feb 16 - Feb 17

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

$159 nightly

$182 total

Jan 18 - Jan 19

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 17 - Jan 18

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

$210 nightly

$237 total

Feb 16 - Feb 17

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

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

$286 nightly

$322 total

Feb 15 - Feb 16

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

Feb 16 - Feb 17

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

Cumberland Forest Cottage - Quiet & Sizable Back Yard!

Monteagle TN

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

Handicap Accessible 4 Bedrooms with Amazing Views on Monteagle Mountain

Monteagle TN

Located in Monteagle, this vacation home is in the mountains, within a 5-minute drive of Harton Park and Monteagle Sunday School Assembly.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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.