Luxury 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 vacation rentals – enter your dates for availability.

Top-rated 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 Winchester

Experience the best of lake life with Wander in Winchester. Our collection of luxury vacation rentals in Winchester, Tennessee combines the polish of a five-star stay with the comfort and privacy of a beautiful home.

Choose from contemporary lakefront residences and tranquil countryside retreats, each professionally operated and styled to look exactly like the photos. Expect expansive living spaces, chef-ready kitchens, dedicated work areas with ultra fast WiFi, and outdoor lounges perfect for unwinding morning to night.

Every stay includes inspiring views, pristine cleaning, and 24/7 concierge service so you can relax from the moment you arrive.

Destinations near Winchester

Featured vacation rentals in Winchester

Home in Winchester

7 bedrooms•5 baths

$2,897 for 2 nights•

5.0

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

Highlights in Winchester

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

Tims Ford State Park

Twin Creeks Marina

The Oldham Theater

Jack Daniel's Distillery

Bear Trace at Tims Ford

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.

Most popular amenities for vacation rentals in Winchester

Other popular amenities & vacation types in Winchester

Family vacation rentals in Winchester

Large group vacation rentals in Winchester

Lakefront vacation rentals in Winchester

Hot tub vacation rentals in Winchester

Private pool vacation rentals in Winchester

Discover more of Winchester

Set beside the deep, clear waters of Tims Ford Lake, Winchester blends small-town charm with wide-open nature. Glassy coves, rolling hills, and starry nights create a peaceful rhythm that makes it easy to slow down.

Spend your days cruising the lake, casting a line, or hiking the trails at Tims Ford State Park. Tee off at The Bear Trace at Tims Ford, then wander the historic courthouse square, or take a scenic drive to Sewanee’s overlooks and Lynchburg’s storied distilleries. Each season brings a new palette, from spring blooms to brilliant fall foliage.

With easy access and a delightfully relaxed pace, this is why Wander's luxury vacation rentals in Winchester, Tennessee 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 vacation rentals?

Wander offers a level of consistency and quality you won’t find with most 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 vacation rentals in Winchester?

Some of our most popular 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 vacation rentals does Wander have available in Winchester?

Wander offers 9 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 vacation rentals in Winchester?

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

Do Wander’s 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.