233+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in Windsor |
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  2. Massachusetts
  3. Windsor

Explore Windsor Golf Retreats

About Windsor Vacation Rentals

Explore over 233 golf accommodation rentals in Windsor. 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 Windsor.

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 Windsor. 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 Windsor offer approximately 1066.03 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 Windsor typically ranges around US $383.

StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Windsor. 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 Windsor

Type Count
Vacation Homes 141
Holiday Apartments 27
Cabin Rentals 12
Cottages 12
Others 6
B&B 4
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windsor

★ 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 Windsor.

Weather in Windsor, MA

View the weather forecast for Windsor before booking your Windsor 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 Windsor Guest Reviews Local Attractions

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


Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Berkshire East Ski Resort
Norman Rockwell Museum
National Shrine of the Divine Mercy
Mohawk Trail State Forest
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Bridge of Flowers
Hancock Shaker Village
Pittsfield State Forest
October Mountain State Forest
Beartown State Forest

Frequently Asked Questions About Windsor?

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

Looking for a place to stay in Windsor? 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 Windsor?

Find exceptional golf retreats with private pools near Windsor 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 Windsor for family stays?

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

How many StayAndPlay golf vacation rentals are available in Windsor?

StayAndPlay, as of 2025, features over 233 unique golf villas, golf hotels, golf resorts, and more in Windsor. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2025, StayAndPlay has curated over 233 stunning properties in Windsor, sourced from trusted platforms. Plan your next golf trip now.

For 2025, StayAndPlay provides access to over 233 premier golf accommodations in Windsor. Find your ideal golf-retreat and play your best game with StayAndPlay.

People Also Ask

There are 14 hotels in Windsor 6 resorts, and 180 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Windsor