Luxury Lakefront Vacation Rentals in Winchester

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 9 lakefront vacation rentals – enter your dates for availability.

Top-rated lakefront vacation rentals in Winchester

Magnolia House Dock, Kayaks, Games, Fire Pit

Home in Winchester

3 bedrooms•3 baths

$910 for 2 nights•

5.0

Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit

Home in Winchester

4 bedrooms•3 baths

$779 for 2 nights•

5.0

Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards

Home in Winchester

5 bedrooms•3 baths

$952 for 2 nights•

5.0

Million Dollar Views + Luxury + Infinity Deck

Home in Winchester

5 bedrooms•3 baths

$1,556 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,398 for 2 nights•

5.0

Home in Winchester

7 bedrooms•5 baths

$2,897 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$1,059 for 2 nights•

5.0

Shimmering Waters-*Rare Find* Best Lot with Dock and Views on Lake

Home in Winchester

5 bedrooms•4 baths

$1,880 for 2 nights•

5.0

Welcome to the lakeside at Winchester

Settle into the shoreline of Tims Ford Lake with Wander’s luxury lakefront vacation rentals in Winchester, Tennessee. Our homes marry the polish of a five-star stay with the privacy of a modern retreat, so you can truly unwind the moment you arrive.

Choose from design-forward residences with sweeping water views, expansive decks, and direct lake access. Many feature private docks, hot tubs, screened porches, and fire pits for long evenings by the water. Expect ultra fast WiFi, chef-grade kitchens, and dedicated workspaces, plus pristine cleaning and 24/7 concierge service. Every detail is expertly managed so the lake is always center stage.

Popular lakefront vacation rentals in Winchester

Home in Winchester

3 bedrooms•3 baths

$910 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$779 for 2 nights•

5.0

Home in Winchester

5 bedrooms•3 baths

$952 for 2 nights•

5.0

Home in Winchester

5 bedrooms•3 baths

$1,556 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,398 for 2 nights•

5.0

Home in Winchester

7 bedrooms•5 baths

$2,897 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$1,059 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,880 for 2 nights•

5.0

New lakefront vacation rentals in Winchester

Home in Winchester

3 bedrooms•3 baths

$910 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$779 for 2 nights•

5.0

Home in Winchester

5 bedrooms•3 baths

$952 for 2 nights•

5.0

Home in Winchester

5 bedrooms•3 baths

$1,556 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,398 for 2 nights•

5.0

Home in Winchester

7 bedrooms•5 baths

$2,897 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$1,059 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,880 for 2 nights•

5.0

Highlights in Winchester

Discover the perfect blend of lakeside recreation, historic downtown charm, and world-famous Tennessee whiskey just a short drive away.

Tims Ford State Park

The Oldham Theater

Bear Trace at Tims Ford

Jack Daniel's Distillery

Short Springs Natural Area

Rutledge Falls

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Winchester

Home in Winchester

3 bedrooms•3 baths

$910 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$779 for 2 nights•

5.0

Home in Winchester

5 bedrooms•3 baths

$952 for 2 nights•

5.0

Home in Winchester

5 bedrooms•3 baths

$1,556 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,398 for 2 nights•

5.0

Home in Winchester

7 bedrooms•5 baths

$2,897 for 2 nights•

5.0

Home in Winchester

4 bedrooms•3 baths

$1,059 for 2 nights•

5.0

Home in Winchester

5 bedrooms•4 baths

$1,880 for 2 nights•

5.0

View all homes

Most popular amenities for lakefront vacation rentals in Winchester

Other popular amenities & vacation types in Winchester

Family vacation rentals in Winchester

Large group vacation rentals in Winchester

Hot tub vacation rentals in Winchester

Private pool vacation rentals in Winchester

Discover more lakeside charm in Winchester

In the foothills of the Cumberland Plateau, Winchester hugs the clear waters of Tims Ford Lake, a maze of quiet coves and open stretches edged by hardwood forests and limestone bluffs. Morning light skims the water and evenings come with broad, starry skies.

Each season offers a different mood. Spring is bright and gentle, summer brings warm days on the water, autumn reflects blazing color across the coves, and winter settles into calm. With easy access from Nashville and Chattanooga, the setting invites unhurried days and soul-deep relaxation. This is why Wander’s luxury lakefront vacation rentals in Winchester are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Winchester

Why should I book a Wander in Winchester over other lakefront vacation rentals?

Wander offers a level of consistency and quality you won’t find with most lakefront vacation rentals.

Every home in Winchester delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular lakefront vacation rentals in Winchester?

Some of our most popular lakefront vacation rentals in Winchester include Magnolia House Dock, Kayaks, Games, Fire Pit, Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit, and Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different lakefront vacation rentals does Wander have available in Winchester?

Wander offers 9 lakefront vacation rentals in Winchester, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s lakefront vacation rentals in Winchester?

You can check-in to Wander lakefront vacation rentals in Winchester after 4.00pm and check-out before 10.00am.

Do Wander’s lakefront vacation rentals in Winchester have WiFi access?

Yes. Every Wander home in Winchester has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.