Explore The Berkshires Golf Retreats
About The Berkshires Vacation Rentals
Explore over 1717 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 1053.92 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 $472.
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.
Top Golf Accommodation Types in The Berkshires
| Type | Count |
|---|---|
| Vacation Homes | 912 |
| Holiday Apartments | 193 |
| Cottages | 79 |
| Cabin Rentals | 61 |
| B&B | 56 |
| Others | 18 |
| Ski Chalet Rentals | 12 |
| Villas | 12 |
| 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.
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
Find Nearby Cabin Rentals in these Cities & Neighborhoods
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:
- Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
- “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
- Unique Condo, Quiet Neighborhood, Walk to Town.
- Devonfield Inn B&B
- A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
- Custom Home on 9 scenic acres near small lake, Sleeps up to 16.
- Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly
- Charming historic cottage on scenic road to Mt. Greylock
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.
- Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
- Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor
- Mountain Blossom Retreat by Evergreen Home
- Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4
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:
- Charming Cottage, New Marlborough Village Green in the Berkshires
- Lakefront Otis Home w/Stunning Views & Boats!
- Whistler's Inn Bed & Breakfast
How many StayAndPlay golf vacation rentals are available in The Berkshires?
StayAndPlay, as of 2026, features over 1717 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 2026, StayAndPlay has curated over 1717 stunning properties in The Berkshires, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 1717 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 | 71 |
