Massachusetts · MA
Berkshire arts country and quiet courses
Best season
May – Oct
Sep · Oct
Trip cost · per golfer
$1,260–$6,900
3-night trip
Nearest airport
ALB
55 mi · Albany
Difficulty
Easy
Handicap 12–32
Overview
Escape to The Berkshires for a tranquil golf getaway, where rolling hills and stunning fall foliage provide a picturesque backdrop to classic New England courses that blend challenge with breathtaking natural beauty.
Top courses
Editor-picked layouts ranked by prestige, conditioning and player experience.
Design by Donald Ross · Par 70 · 6,078 yds
A historic Donald Ross design offering stunning views and a challenging, yet enjoyable, round. Play in the fall to experience the vibrant foliage that makes this course truly special.
Design by Wayne Stiles, John Van Kleek · Par 71 · 6,649 yds
Consistently ranked among the top collegiate courses, Taconic offers a traditional New England layout with elevation changes. Walking this course offers the best experience, but be prepared for some uphill climbs.
Design by Russ Kinney · Par 72 · 6,548 yds
A challenging championship course with elevation changes and panoramic views of the Berkshire Mountains. Don't miss the BBQ at the clubhouse after your round – it's a local favorite.
Design by A.W. Tillinghast (original nine) · Par 70 · 5,744 yds
An incredibly scenic and historic course nestled in the Southern Berkshires, offering a fun and accessible round. The course is very walkable and offers a relaxed pace, perfect for a casual round.
Stay & play
Resort packages bundle lodging, rounds, range access, and on-site dining. Hotel-only options give you flexibility to course-hop.
Luxury Resort
An all-inclusive luxury wellness resort with a focus on holistic well-being.
Historic Inn
A historic inn in Stockbridge offering classic New England charm and hospitality.
Boutique Hotel
A chic boutique hotel in downtown Pittsfield with modern amenities and unique design.
Motel/Inn
A comfortable and affordable option in Lenox, offering a pleasant stay near attractions.
Off the course
Non-golf experiences worth building into your trip — from local landmarks to nature, food, and culture.
Attend a concert at the summer home of the Boston Symphony Orchestra.
Explore the extensive collection of original Norman Rockwell artworks and his studio.
Ascend the highest peak in Massachusetts for stunning panoramic views.
Experience world-renowned dance performances at this historic outdoor venue.
Browse unique boutiques, art galleries, and enjoy diverse dining options in this vibrant town.
Itineraries
Choose your trip length. Each plan is built around the marquee courses, with rest, dining, and travel days dialed in.
Day 1
Land at ALB, transfer to your hotel, hit the range, and grab a casual dinner at Mezze Bistro + Bar.
Day 2
Morning tee time at Wyndhurst Manor & Club (Formerly Cranwell Resort). Lunch at the clubhouse, afternoon recovery, dinner at Frankie's Ristorante.
Day 3
Early tee time at Egremont Country Club, light lunch, then transfer back to ALB.
Budget
Realistic ranges sourced from current resort rates, public green fees, and group dining averages.
Lodging 3 nights · $180/nt | $540 |
Golf 2 rounds · $120 avg | $240 |
Food & drink ~$110/day | $330 |
Ground transport Rideshare + cart fees | $180 |
Flights Search Skyscanner for live fares | Variable |
| Estimated total · per golfer | $1,290 |
Season
Hill country mild
When to book: 1-2 months out
Dining
From clubhouse classics to chef-driven dinners worth a reservation.
Mediterranean
Farm-to-table Mediterranean cuisine with a focus on fresh, local ingredients.
American
A popular farm-to-table restaurant in Great Barrington known for its rustic ambiance.
Italian
A beloved local spot serving classic Italian dishes in a cozy setting.
Modern American
Creative modern American dishes with an emphasis on seasonal produce.
Pizza
Delicious wood-fired sourdough pizzas with unique toppings and a lively atmosphere.
Pub Fare
A classic Irish pub offering hearty pub fare, a great beer selection, and a friendly vibe.
After dark
Where the buddy trips end up after the 19th hole.
Pub
A cozy, classic pub located in The Red Lion Inn, offering live music on weekends.
Brewpub
A popular local brewery in North Adams with a lively taproom and various craft beers.
Brewery/Restaurant
The first brewery to open in Massachusetts since Prohibition, offering house-brewed beers and pub food.
Tee times
Live inventory from GolfNow plus flight comparison from Skyscanner. Prices update in real time.
FAQ
May – Oct (Sep, Oct). Hill country mild
Plan on $1,260–$6,900 per golfer for a 3-night trip including lodging, rounds, food and ground transport. Flights are extra.
ALB, about 55 miles from the resort area. Most national hubs offer non-stop service via Albany.
3 nights is the sweet spot — enough for 2 full rounds plus a rest or sightseeing day.
Yes — popular with Couples. Quieter evenings, ideal for golf-focused groups.
Ready to book
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Trip snapshot
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