The Berkshires Golf Vacations 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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4 Night Golf vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.

Jiminy Peak Mountain Resort

$575

per person

Sep 14 - Sep 18

found 6 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Albany (ALB)

8.2/10 Very Good! (1,003 reviews)

Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall.

Reviewed on Aug 6, 2026

Quality Inn Lee - Lenox South

$598

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Salt Lake City (SLC) to Albany (ALB)

8.4/10 Very Good! (1,007 reviews)

The Red Lion Inn

$638

per person

Sep 14 - Sep 18

found 6 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Albany (ALB)

8.8/10 Excellent! (1,010 reviews)

Property is tired. Carpeting needs to be replaced. Room furniture needs to be replaced/TVs updated. Staff was very accomodating, helpfull, energetic.

Reviewed on Aug 6, 2026

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How can I find the best golf vacations in The Berkshires?

Swing into the best golf packages in The Berkshires. Punch in your travel dates then filter your results by guest and star rating, popular locations, and amazing extras like spas, pools, and ocean views.

Can I book cheap golf packages in The Berkshires?

Glorious golf on a budget is just a few clicks away. Sort your search results by price or deals to find amazingly affordable luxury golf. Right now, The Berkshires golf packages start at just $575. Prices and availability are subject to change. Additional terms may apply.

How can I find The Berkshires golf and spa packages?

If you long for a little tea tree before you tee off, a golf and spa package will keep you on your A game. Check the spa filter to take your pick from luxurious lodgings where you can live the dream after a round of 18.

How can I find luxury golf resort packages in The Berkshires?

Bag yourself a stay steps from a luxurious championship course by checking the 5* filter. Sort your results by rating to explore a little more extravagance and glam up your getaway with business class flights.

How can I look for The Berkshires casino golf packages?

Ch-ch-check the casino filter for cha-cha-ching-tastic casino and golf packages. From the pristine course to the baize of the roulette wheel, all you’ll see is green.

Can I book The Berkshires golf packages with airfare?

Get serious air before you reach the course by booking your accommodation, flights, and car rental as a package. You can bag a better deal this way—and level up the convenience while you’re at it.

Why should I book a golf vacation for couples in The Berkshires?

If you’ve both got love for the clubs, a couple’s golf vacation is a hole in one. Book accommodation with a full-service spa, exclusive Champagne bar, and outdoor experiences to dip into before and after a round. Together.

Can I book a golf holiday in The Berkshires with free cancellation and/or flexible dates?

Grab a great golf getaway with free cancellation by filtering by payment option. You can find buy now, pay later options this way, too.

Why should I book my golf trip to The Berkshires with Expedia?

We put(t) an amazing choice of golf resorts in one place, so you can hit the fairway every time. And our trips are ATOL protected for extra peace of mind.

Top Golf The Berkshires Hotels

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

34 min drive from Tanglewood Music Center

Stay at this hotel in Hancock. Enjoy free parking, 2 hot tubs, and breakfast (surcharge). Our guests praise the property condition in our reviews. Popular attractions ...

8.2/10 Very Good! (1,004 reviews)

Travelers like: golf course nearby, bar

Travelers say...

"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge ..."

Reviewed on Aug 6, 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

23 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...

The Orchards Hotel

222 Adams Rd Williamstown MA

59 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Massachusetts Museum of Contemporary ...

See all 1,079 properties in The Berkshires

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.