Luxury Vacation Rentals for Large Groups 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 8 large group vacation rentals – enter your dates for availability.

Top-rated large group 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

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

Lakeside Retreat-New Lakeside Home w/kayaks, Game Room, Billiards

6 bedrooms•4 baths

•

~$85 less than other sites

Welcome to your large group retreat in Winchester

Bring everyone together in style with Wander’s luxury vacation rentals in Winchester, Tennessee. Our stays blend five-star consistency with the comfort of a private retreat, so hosting a crowd feels easy from arrival to checkout.

Perfect for large groups, our properties feature expansive great rooms, generous dining for the whole crew, chef-ready kitchens with ample prep space, and multiple bedroom suites for privacy. Expect ultra fast WiFi, pristine cleaning, and 24/7 concierge support, plus thoughtful touches like dedicated work areas and indoor to outdoor gathering zones.

From milestone reunions to productive offsites, book with confidence. The home will look exactly like the photos and operate with hotel-grade precision.

Available soon 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

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

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

Lakeside Retreat-New Lakeside Home w/kayaks, Game Room, Billiards

6 bedrooms•4 baths

•

~$85 less than other sites

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

Whispering Waters

4 bedrooms•3 baths

•

~$85 less than other sites

Paradise Resort

7 bedrooms•5 baths

•

~$175 less than other sites

Lakeside Retreat-New Lakeside Home w/kayaks, Game Room, Billiards

6 bedrooms•4 baths

•

~$85 less than other sites

View all homes

Highlights in Winchester

Gather your group for an unforgettable Tennessee getaway featuring expansive lakes, historic tours, and scenic outdoor adventures.

Tims Ford State Park

Twin Creeks Marina

Jack Daniel's Distillery

Bear Trace at Tims Ford

Montana Drive-In

The Oldham Theater

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 large group vacation rentals in Winchester

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Discover more large groups activities in Winchester

Set beside the clear waters of Tims Ford Lake, Winchester pairs small-town warmth with wide-open nature. Drift through quiet coves, cast for smallmouth bass, or follow shaded trails in Tims Ford State Park with views across the Cumberland foothills.

Days can range from tee times at The Bear Trace at Tims Ford to unhurried moments on the historic town square, then sunset on the water. Add easy excursions to Lynchburg’s famed distillery or Sewanee’s bluff-top overlooks. Spring blooms, long summer days on the lake, and vivid fall color make timing effortless.

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 large group vacation rentals?

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

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

Wander offers 8 large group 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 large group vacation rentals in Winchester?

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

Do Wander’s large group 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.