Holiday rentals near Winton Country Club

We found 357 holiday rentals — enter your dates for availability

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August 2025

September 2025

Select the perfect private holiday rental that's near Winton Country Club. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Winton Country Club

Showing deals for:14 Nov - 21 Nov

Unique mid mod home and furnishings with tons of natural light.

Exceptional

(38 reviews)

Unique Midcentury Minimalist w/ Natural Light in the Heart of LYH

Lynchburg, VA

7% off

NZ$476 nightly

Includes taxes & fees

Exceptional

(34 reviews)

Welcome Home! New luxurious home awaits - large family room w/ fireplace.

Madison Heights, VA

8% off

NZ$514 nightly

Includes taxes & fees

Exceptional

(17 reviews)

#NoCleaningFee! Pool Table, Hot tub, fireplace overlooking Wreck Island Creek

Appomattox, VA

13% off

NZ$589 nightly

Includes taxes & fees

Exceptional

(41 reviews)

Charming Riverside Cottage on 5 Acres- Perfect for Couples & Nature Lovers

Piedmont, VA

7% off

NZ$346 nightly

Includes taxes & fees

Exceptional

(13 reviews)

Country Farmhouse: Fire Pit, Grill, Updated Amenities, Cows, Stars and Solitude

Monroe, VA

8% off

NZ$332 nightly

Includes taxes & fees

Looking to the West at the Blue Ridge Mountains in the background.

Exceptional

(65 reviews)

Blue Ridge, Tye River, C-Ville, Crabtree, Wintergreen, Sweet Briar, Farm

Arrington, VA

8% off

NZ$615 nightly

Includes taxes & fees

Cozy living room with an XL Sectional, perfect for gathering with family or friends.

Exceptional

(7 reviews)

Charming 5BR | Near LU by Saydrajanes Properties

Lynchburg, VA

11% off

NZ$532 nightly

Includes taxes & fees

Exceptional

(137 reviews)

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

Roseland, VA

8% off

NZ$588 nightly

Includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Winton Country Club

Cabins are feet from north fork of Tye River

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Sleeps 3 · 1 bedroom · 1 bathroom

Welcome to Elmwood Acres: an 1890's, 5BR/3.5BA farmhouse situated among hundreds of acres of pastures and orchards with jaw-dropping mountain views, a heated pool, hiking trails, huge yard, and several barns converted into a playhouse and man cave.

Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries

Sleeps 14 · 5 bedrooms · 3 bathrooms

Boho Mountain is a 3br / 2bath in the Heart of Nelson County with a huge heated pool, hot tub, game shed, and incredible mountain views!

Ideal for a large family, few couples, or girlfriends to spend a long weekend / mountain getaway

Sleeps 8 · 3 bedrooms · 2 bathrooms

Charlie's Hideout - A Modern Historic Retreat - Your Home Away From Home!

Sleeps 8 · 4 bedrooms · 2 bathrooms

Top rated rentals - Winton Country Club

Premier Host

Weekend Getaway

Wow! Upon pulling up we were amazed with the location but as soon as we entered the front door, it was absolutely stunning! The cabin itself is SO CLEAN!!! We enjoyed sitting out on the large deck enjoying the view. There is a walking path that is cleared that we enjoyed as well! The host John was wonderful and we will definitely be back!! If I could give more STARS I would!

Traci D.

Stayed Mar 2025

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value