The Berkshires Golf Holidays

Book a Golf Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau
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Find amazing golf holidays in The Berkshires

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

Tee off your top golfing holiday in The Berkshires by searching for the perfect accommodation on Expedia. Pop in your dates and start looking at your options. You can even check and book flights, too – just don’t forget to include your golf bag as luggage!

Are there cheap golf packages available in The Berkshires?

Bundling your accommodation, flights and car hire together is a great way to save money and ensure everything is easily organised. We have stacks of very tempting luxury and cheap golf packages, with those in The Berkshires starting from . Prices and availability are subject to change. Additional terms may apply.

Can I book The Berkshires golf and spa packages?

There’s no better way to unwind after a step-heavy day on the course than with a few hours in the spa. Or, for golf-widowed husbands or wives, a golf and spa package holiday could be a winning way to spend some quality time together, with activities to keep everyone happy. Use the spa filter to find golf holidays in The Berkshires with that added level of bliss.

How can I find luxury golf holidays in The Berkshires?

Score under par on the course and go overboard on everything else with a luxury golf holiday to The Berkshires. To find the most special spots, use the 5-star properties filter, and – go on – treat yourself to business class flights.

Can I book all-inclusive golf holidays in The Berkshires?

Use the all-inclusive filter to hunt out those glorious all-inclusive golf holidays in The Berkshires. If there are none available, consider half board – you’ll likely be out on the golf course at lunchtime anyway.

Why should I book The Berkshires golf holidays including flights?

Save money, save time and save paperwork by booking your accommodation, flights and even car hire all with Expedia. It takes just a few clicks to see all the options and book in one fell swoop.

Should I book a last-minute golf holiday in The Berkshires?

If you have free time on your side or annual leave to use up, a spontaneous last-minute golf trip in The Berkshires is a wonderful idea. Pop in a few dates to see what’s available – you might even save money with last-minute deals.

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

Flexibility is the spice of life, so use our dedicated filter to find accommodation and flights with free cancellation options. Remember, though, always check the small print before booking!

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

Booking a golf trip to The Berkshires with Expedia feels like getting a hole-in-one on your first shot on the course. It’s smooth, easy and, with so many options to choose from, you’ll feel giddy with excitement.

Top Golf The Berkshires Hotels

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
  • 34 min drive from Tanglewood Music Center
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 bars/lounges. Our guests praise the property condition in their reviews. Popular ...
8.2/10 Very Good! (943 reviews)
"Beautiful setting. Friendly staff."

Reviewed on 30 Jun 2025

Jiminy Peak Mountain Resort
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
  • 23 min drive from Tanglewood Music Center
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (633 reviews)
Great place for a stopover, thank you!
"We love staying here in transit to and from Maine and New York every summer. Such a pleasure to know that there are great staff and a great pool! (thank you for always keeping it warm and clean) I'm sure the pool will need to be repainted/resurfaced soon (maybe wait until winter!), but it is always ..."

Reviewed on 26 Jun 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Orchards Hotel
The Orchards Hotel
2.5 out of 5
222 Adams Rd, Williamstown, MA
  • 59 min drive from Tanglewood Music Center
Stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Colonial Plaza and Linear Park are ...

Travellers like: golf course nearby, golf lessons nearby

Travellers say...
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on 9 Mar 2020

The Orchards Hotel
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.