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

Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit

4 bedrooms•3 baths

•

~$60 less than other sites

Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards

5 bedrooms•3 baths

•

~$75 less than other sites

Billion Dollar Views

5 bedrooms•4 baths

Million Dollar Views + Luxury + Infinity Deck

5 bedrooms•3 baths

•

~$90 less than other sites

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

5 bedrooms•4 baths

•

~$100 less than other sites

Magnolia House Dock, Kayaks, Games, Fire Pit

3 bedrooms•3 baths

•

~$50 less than other sites

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

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

Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit

4 bedrooms•3 baths

•

~$60 less than other sites

Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards

5 bedrooms•3 baths

•

~$75 less than other sites

Billion Dollar Views

5 bedrooms•4 baths

Million Dollar Views + Luxury + Infinity Deck

5 bedrooms•3 baths

•

~$90 less than other sites

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

5 bedrooms•4 baths

•

~$100 less than other sites

Magnolia House Dock, Kayaks, Games, Fire Pit

3 bedrooms•3 baths

•

~$50 less than other sites

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

New lakefront vacation rentals in Winchester

Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit

4 bedrooms•3 baths

•

~$60 less than other sites

Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards

5 bedrooms•3 baths

•

~$75 less than other sites

Billion Dollar Views

5 bedrooms•4 baths

Million Dollar Views + Luxury + Infinity Deck

5 bedrooms•3 baths

•

~$90 less than other sites

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

5 bedrooms•4 baths

•

~$100 less than other sites

Magnolia House Dock, Kayaks, Games, Fire Pit

3 bedrooms•3 baths

•

~$50 less than other sites

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

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

Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit

4 bedrooms•3 baths

•

~$60 less than other sites

Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards

5 bedrooms•3 baths

•

~$75 less than other sites

Billion Dollar Views

5 bedrooms•4 baths

Million Dollar Views + Luxury + Infinity Deck

5 bedrooms•3 baths

•

~$90 less than other sites

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

5 bedrooms•4 baths

•

~$100 less than other sites

Magnolia House Dock, Kayaks, Games, Fire Pit

3 bedrooms•3 baths

•

~$50 less than other sites

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

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 Barefoot Bliss Stunning Views, Pool, Kayaks, & Firepit, Barefoot Dreams Waterfont w/Flat Lot, Pool, Paddleboards, and Billion Dollar Views. 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.