106+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in Pittsfield |
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Explore Pittsfield Golf Retreats

About Pittsfield Vacation Rentals

Explore over 106 golf accommodation rentals in Pittsfield. 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 Pittsfield.

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 Pittsfield. 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 Pittsfield offer approximately 1164.12 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 Pittsfield typically ranges around US $383.

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

Type Count
Vacation Homes 63
Holiday Apartments 10
Cottages 4
Cabin Rentals 3
Others 1

Use these Quick Filters to Find a Vacation Rental in Pittsfield

★ 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 Pittsfield.

Weather in Pittsfield, MA

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

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


Bousquet Ski Area
Berkshire Museum
Hancock Shaker Village
Pittsfield State Forest
Colonial Theater
Canoe Meadows Wildlife Sanctuary
Berkshire Athenaeum
Herman Melville's Arrowhead
Guido's Marketplace
Barrington Stage Company
Crane Museum of Papermaking
Arrowhead Museum
Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Ski Butternut
Catamount Ski Area
Berkshire East Ski Resort
Norman Rockwell Museum

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Pittsfield State Forest 463 Properties
Guido's Marketplace 122 Properties
Bousquet Ski Area 120 Properties
Herman Melville's Arrowhead 92 Properties
Arrowhead Museum 92 Properties
Colonial Theater 89 Properties
Berkshire Museum 87 Properties
Berkshire Athenaeum 84 Properties
Canoe Meadows Wildlife Sanctuary 83 Properties
Barrington Stage Company 81 Properties
Crane Museum of Papermaking 77 Properties
Hancock Shaker Village 49 Properties

Frequently Asked Questions About Pittsfield?

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

Looking for a place to stay in Pittsfield? 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 Pittsfield?

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

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

How many StayAndPlay golf vacation rentals are available in Pittsfield?

StayAndPlay, as of 2026, features over 106 unique golf villas, golf hotels, golf resorts, and more in Pittsfield. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2026, StayAndPlay has curated over 106 stunning properties in Pittsfield, sourced from trusted platforms. Plan your next golf trip now.

For 2026, StayAndPlay provides access to over 106 premier golf accommodations in Pittsfield. Find your ideal golf-retreat and play your best game with StayAndPlay.

People Also Ask

There are 16 hotels in Pittsfield 2 resorts, and 76 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Pittsfield