Luxury Vacation Rentals in Winchester

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

Wander Winchester Magnolia

Home in Winchester, TN

Wander Winchester Magnolia

$139 for 1 night•
5
3 bedrooms•3 beds•3 baths
Wander Winchester Shores

Home in Winchester, TN

Wander Winchester Shores

$139 for 1 night•
5
4 bedrooms•4 beds•3.5 baths
Wander Winchester Hills

Home in Winchester, TN

Wander Winchester Hills

$169 for 1 night•
4.98
4 bedrooms•4 beds•3.5 baths
Wander Winchester Serenity

Home in Winchester, TN

Wander Winchester Serenity

$159 for 1 night•
5
5 bedrooms•5 beds•3 baths
Wander Winchester Waterfront

Home in Winchester, TN

Wander Winchester Waterfront

$299 for 1 night•
4.99
5 bedrooms•5 beds•4 baths
Wander Winchester Evergreen

Home in Winchester, TN

Wander Winchester Evergreen

$249 for 1 night•
5
6 bedrooms•6 beds•4 baths
Wander Winchester Vista

Home in Winchester, TN

Wander Winchester Vista

$599 for 1 night•
4.97
7 bedrooms•7 beds•5 baths
Wander Winchester Creeks

Home in Winchester, TN

Wander Winchester Creeks

$389 for 1 night•
5
5 bedrooms•5 beds•4 baths
Welcome to Winchester

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

Franklin
Franklin
Nashville
Nashville
Gallatin
Gallatin
Walland
Walland
Pigeon Forge
Pigeon Forge
Sevierville
Sevierville
Gatlinburg
Gatlinburg
Cosby

Popular vacation rentals in Winchester

Wander Winchester Magnolia

Home in Winchester, TN

Wander Winchester Magnolia

$139 for 1 night•
5
3 bedrooms•3 beds•3 baths
Wander Winchester Shores

Home in Winchester, TN

Wander Winchester Shores

$139 for 1 night•
5
4 bedrooms•4 beds•3.5 baths
Wander Winchester Hills

Home in Winchester, TN

Wander Winchester Hills

$169 for 1 night•
4.98
4 bedrooms•4 beds•3.5 baths
Wander Winchester Serenity

Home in Winchester, TN

Wander Winchester Serenity

$159 for 1 night•
5
5 bedrooms•5 beds•3 baths
Wander Winchester Waterfront

Home in Winchester, TN

Wander Winchester Waterfront

$299 for 1 night•
4.99
5 bedrooms•5 beds•4 baths
Wander Winchester Evergreen

Home in Winchester, TN

Wander Winchester Evergreen

$249 for 1 night•
5
6 bedrooms•6 beds•4 baths
Wander Winchester Vista

Home in Winchester, TN

Wander Winchester Vista

$599 for 1 night•
4.97
7 bedrooms•7 beds•5 baths
Wander Winchester Creeks

Home in Winchester, TN

Wander Winchester Creeks

$389 for 1 night•
5
5 bedrooms•5 beds•4 baths

Available soon in Winchester

Wander Winchester Shores

Home in Winchester, TN

Wander Winchester Shores

$318 for 2 nights•
5
4 bedrooms•4 beds•3.5 baths
Wander Winchester Serenity

Home in Winchester, TN

Wander Winchester Serenity

$303 for 2 nights•
5
5 bedrooms•5 beds•3 baths
Wander Winchester Creeks

Home in Winchester, TN

Wander Winchester Creeks

$773 for 2 nights•
5
5 bedrooms•5 beds•4 baths

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.

All homes in Winchester

Wander Winchester Magnolia

Home in Winchester, TN

Wander Winchester Magnolia

$139 for 1 night•
5
3 bedrooms•3 beds•3 baths
Wander Winchester Shores

Home in Winchester, TN

Wander Winchester Shores

$139 for 1 night•
5
4 bedrooms•4 beds•3.5 baths
Wander Winchester Hills

Home in Winchester, TN

Wander Winchester Hills

$169 for 1 night•
4.98
4 bedrooms•4 beds•3.5 baths
Wander Winchester Serenity

Home in Winchester, TN

Wander Winchester Serenity

$159 for 1 night•
5
5 bedrooms•5 beds•3 baths
Wander Winchester Waterfront

Home in Winchester, TN

Wander Winchester Waterfront

$299 for 1 night•
4.99
5 bedrooms•5 beds•4 baths
Wander Winchester Evergreen

Home in Winchester, TN

Wander Winchester Evergreen

$249 for 1 night•
5
6 bedrooms•6 beds•4 baths
Wander Winchester Vista

Home in Winchester, TN

Wander Winchester Vista

$599 for 1 night•
4.97
7 bedrooms•7 beds•5 baths
Wander Winchester Creeks

Home in Winchester, TN

Wander Winchester Creeks

$389 for 1 night•
5
5 bedrooms•5 beds•4 baths
View all homes

Most popular amenities for vacation rentals in Winchester

Boat Dock (7)
Hot Tub (5)
Movie Theater (2)
Wet Bar (2)
Guest House (1)
Outdoor pool (3)
Water Slide (2)
Kayaks (4)
Lake Access (9)
Waterfront (3)
Lake View (9)
Putting Green (1)
Patio (9)
Bbq Area (9)
Arcade Machine (7)
Sound System (4)

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

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 Wander Winchester Magnolia, Wander Winchester Shores, and Wander Winchester Hills. 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.