The Berkshires Golf Vacations
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Top Golf vacation packages in The Berkshires
- Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Jan 2 - Jan 6Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires + Flight
South Lee4 nights3.5 star property9.2/10 - Wonderful (1,002 reviews)Roundtrip • Fort Lauderdale (FLL) - Albany (ALB)FLL - BOS • Nonstop BOS - FLL • 1 stop$973$909found 21 hours agoper traveler - The Red Lion Inn
Dec 25 - Dec 27The Red Lion Inn + Flight
Stockbridge2 nights3.5 star property8.8/10 - Excellent (1,010 reviews)"We stayed in an adjacent house owned by the hotel. When we booked we assumed we’d be in the main hotel. The “out” building was unmarked and hard to find. It was dark when we arrived and there were no porch lights. We thought the overall experience was good. Quaint but this building could benefit from some upgrades."Reviewed November 7, 2026Roundtrip • New York (NYC) - Albany (ALB)LGA - ALB • 1 stop ALB - LGA • Nonstop$1,118$1,071found 1 day agoper traveler - Holiday Inn Express Hotel & Suites Great Barrington by IHG
Jan 2 - Jan 6Holiday Inn Express Hotel & Suites Great Barrington by IHG + Flight
Great Barrington4 nights2.5 star property8.8/10 - Excellent (854 reviews)Roundtrip • Fort Lauderdale (FLL) - Albany (ALB)FLL - BOS • Nonstop BOS - FLL • 1 stop$963$925found 21 hours agoper traveler - 636 S Main St
Dec 25 - Dec 27636 S Main St + Flight
Lanesborough2 nights2.0 star propertyRoundtrip • New York (NYC) - Albany (ALB)LGA - ALB • 1 stop ALB - LGA • Nonstop$1,341$1,296found 1 day agoper traveler - The Black Swan Lee - Lenox, an Ascend Collection Hotel
Jan 2 - Jan 6The Black Swan Lee - Lenox, an Ascend Collection Hotel + Flight
Lee4 nights3.0 star property9.2/10 - Wonderful (1,001 reviews)"😊"Reviewed November 7, 2026Roundtrip • Fort Lauderdale (FLL) - Albany (ALB)FLL - BOS • Nonstop BOS - FLL • 1 stop$1,011$984found 21 hours agoper traveler
Discover the most popular places to visit in The Berkshires
Massachusetts Museum of Contemporary Art
Top Golf The Berkshires Hotels
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires"This place was amazing to stay at! The staff was friendly and helpful. The building was beautifully decorated inside and out, and it is in a safe location. Breakfast was very good. Only downside is that coffee was not available throughout the day (only served at breakfast). Overall, would definitely stay here again!"
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel"😊"
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
"We were two families satying for two nights Pros - kitchen in the suite, location, accessible to stores and restaurants, close to many scenic locations Cons - the building is very old, the furniture makes squeaky noise, toilet seat was broken, the room was smelling of eggs when we checked in. The carpet was not steam cleaned in a very long time."
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast"Delightful experience in a gilded age setting."
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
Find amazing golf vacations in The Berkshires
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 $909. 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.