1584+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in The Berkshires |
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Explore The Berkshires Golf Retreats

About The Berkshires Vacation Rentals

Explore over 1584 golf accommodation rentals in The Berkshires. 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 The Berkshires.

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 The Berkshires. 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 The Berkshires offer approximately 1043.49 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 The Berkshires typically ranges around US $445.

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

Type Count
Vacation Homes 830
Holiday Apartments 177
Cottages 73
Cabin Rentals 57
B&B 56
Others 23
Villas 12
Ski Chalet Rentals 11
Unique Vacation Rentals 2

Use these Quick Filters to Find a Vacation Rental in The Berkshires

★ 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 The Berkshires.

Weather in The Berkshires, MA

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

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


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

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Berkshire County 1,166 Properties
Hancock 172 Properties
Jiminy Peak Mountain Resort 172 Properties
Great Barrington 163 Properties
Lenox 129 Properties
Williamstown 106 Properties
Pittsfield 87 Properties
Lee 69 Properties
Becket 49 Properties
Stockbridge 44 Properties
Monterey 42 Properties
Otis 39 Properties

Frequently Asked Questions About The Berkshires?

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

Looking for a place to stay in The Berkshires? 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 The Berkshires?

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

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

How many StayAndPlay golf vacation rentals are available in The Berkshires?

StayAndPlay, as of 2025, features over 1584 unique golf villas, golf hotels, golf resorts, and more in The Berkshires. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2025, StayAndPlay has curated over 1584 stunning properties in The Berkshires, sourced from trusted platforms. Plan your next golf trip now.

For 2025, StayAndPlay provides access to over 1584 premier golf accommodations in The Berkshires. Find your ideal golf-retreat and play your best game with StayAndPlay.

Nearby Neighborhood (1) 
Neighborhood Property Count
Sherwood Forest Golf Rental Cottages and Golf Getaways in Massachusetts 54

People Also Ask

There are 124 hotels in The Berkshires 73 resorts, and 1076 rentals

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