396+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in Winchester |
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  2. Virginia
  3. Winchester

Explore Winchester Golf Retreats

About Winchester Vacation Rentals

Explore over 396 golf accommodation rentals in Winchester. From luxurious golf villas to cozy golf cabins, golf resorts, and exclusive golf hotels, each offers premium amenities designed for families, groups, and golf enthusiasts. Enjoy exceptional comfort and a one-of-a-kind golf experience with these incredible accommodations. Perfect for tranquil golf escapes, relaxing retreats, or golf-inspired getaways, these properties provide style and comfort in Winchester.

Looking for last-minute deals or the best offers on golf villas, golf cabins, golf resorts, and other golf retreats? StayAndPlay makes it easy to compare options in Winchester. Choose from spacious family-friendly stays, charming golf escapes, or luxurious golf retreats tailored for ultimate relaxation and play.

Find spacious family-friendly golf accommodations, golf cottage, or luxurious golf villas—all designed for maximum comfort and convenience during your visit.

On average, golf accommodation rentals in Winchester offer approximately 1034.55 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning golf course surroundings.

The average nightly rate for golf accommodation rentals in Winchester typically ranges around US $337.

StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Winchester. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.

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Top Golf Accommodation Types in Winchester

Type Count
Vacation Homes 153
Holiday Apartments 66
Cabin Rentals 52
Cottages 17
Villas 10
Ski Chalet Rentals 7
Others 3
B&B 1
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Winchester

★ Pro Tip: StayAndPlay simplifies your search for the best golf accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore golf villas, cozy golf cabins, golf hotels, and golf resorts. Filter by availability, pricing, cancellation options, and amenities to discover the ideal golf retreat in Winchester.

Weather in Winchester, VA

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Winchester Guest Reviews Local Attractions

StayAndPlay offers a diverse selection of the top golf villas, golf hotels, and other golf retreats around the world. Winchester Guest Reviews Find the Best Golf Experiences & Activities for Your Golf Trip


SheNonedoah University
Front Royal Entrance SheNonedoah National Park
Winchester Medical Center
Bluemont Vineyard
Skyline Caverns
Dinosaur Land
Apple Blossom Mall
Mt Hebron Cemetery
Jim Barnett Park
SheNonedoah Valley Discovery Museum
Wilson's Wild Animal Park
Patsy Cline Historic House
Twin Oaks Tavern Winery
Blue Ridge Arts Council and Gallery
Bing Crosby Stadium
Watermelon Park Campground
Winchester Little Theater
Holy Cross Abbey
Mackintosh Fruit Farm
Hupp's Hill Civil War Park

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Warren County 164 Properties
Frederick County 160 Properties
Front Royal 150 Properties
Happy Creek 143 Properties
Old Town Winchester 127 Properties
Clarke County 62 Properties
Strasburg 62 Properties
Paris 59 Properties
Berryville 37 Properties
Bluemont 34 Properties
Russell 27 Properties
Stephens City 25 Properties

Frequently Asked Questions About Winchester?

What are the best golf resorts, luxury villas, and vacation rentals in Winchester?

Looking for a place to stay in Winchester? Explore these highly-rated golf vacation rentals for a one-of-a-kind golf retreat, where you can relax, unwind, and get ready to play your best game:

How many golf stays with private pools are available in Winchester?

Find exceptional golf retreats with private pools near Winchester on StayAndPlay. Relax in serene golf vacation rentals with exclusive pool access and picturesque golf course views. Whether it's a spacious golf villa or a secluded golf cabin, these properties offer the perfect blend of luxury and relaxation, so you can focus on your game.

What are the top-rated golf retreats in Winchester for family stays?

Searching for a family-friendly golf retreat in Winchester? Explore these top-rated options, each loved by families and groups who have stayed in Winchester:

How many StayAndPlay golf vacation rentals are available in Winchester?

StayAndPlay, as of 2025, features over 396 unique golf villas, golf hotels, golf resorts, and more in Winchester. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2025, StayAndPlay has curated over 396 stunning properties in Winchester, sourced from trusted platforms. Plan your next golf trip now.

For 2025, StayAndPlay provides access to over 396 premier golf accommodations in Winchester. Find your ideal golf-retreat and play your best game with StayAndPlay.

People Also Ask

There are 83 hotels in Winchester and 281 rentals

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