Winchester Vacation Rentals

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Vacation Rentals in Winchester

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

Pelham TN

$169 nightly

$193 total

Apr 20 - Apr 21

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.

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

Monteagle TN

$290 nightly

$326 total

May 20 - May 21

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.

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

Monteagle TN

$228 nightly

$257 total

May 20 - May 21

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.

On the University of the South campus, Sewanee, TN.

Sewanee TN

$559 nightly

$638 total

May 20 - May 21

Total with taxes and fees

When you stay at this vacation home in Sewanee, you'll be on a lake, within a 10-minute walk of Manigault Park and duPont Library.

Bonnaroo,Sewanee,Hikes, Caverns: Basecamp Tiny

Monteagle TN

$201 nightly

$201 total

May 5 - May 6

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.

Mountain Memories to provide a cozy retreat on your vacation!

Monteagle TN

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.

S'mores & More Tiny House - Tracy City

Tracy City TN

$283 nightly

$332 total

Apr 20 - Apr 21

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.

Cove Sweet Cove - 3BR + 2BR Near the Caverns!

Pelham TN

Located in Pelham, this vacation home is in a rural location, within a 10-minute drive of Elk River and Monteagle Sunday School Assembly.

Hiker's Hangout Monteagle

Monteagle TN

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

Lynchburg Getaway walking distance 2 Jack Daniel’s

Lynchburg TN

With a stay at this vacation home in Lynchburg, you'll be within a 15-minute walk of Jack Daniel's Distillery and Lynchburg Hardware and General Store.

Brand New! Eagle's Nest Tiny House

Monteagle TN

With a stay at this vacation home in Monteagle (Clifftops), you'll be within a 10-minute drive of Sam H. Werner Military Museum and Clifftops Lake.

Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,

Winchester TN

With a stay at this vacation home in Winchester, you'll be on the waterfront, just steps from Tims Ford Lake and a 5-minute drive from Elk River.

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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.