May is the best golf weather month in New England, and it serves a very useful double duty. Kids aren't out of school yet and vacation time generally hasn't started, which leaves you pure high-60s and low-70s sun and off-peak rates at some of the best places.
The Cranwell Resort is tucked into the Berkshires in Western Massachusetts, about two hours from Boston and two and half from New York City. The majestic main building started as a sprawling summer home for a Vanderbilt scion, and in the 100 years since has variously been a hunt and country club and school for boys.
Now, it's a high-end resort set on 380 acres, with a luxurious spa and a vintage, sporty Stiles and Van Cleek layout. The course was laid out in 1926, and is a worthy comparison to the most interesting Donald Ross designs of the same era. It only plays 6,300 yards from the tips, but the combination of clever green complexes and subtle sidehill fairway lies make it entertaining challenge worth a few replays. The two nines play almost like different courses, with the front more open and the back set back in mature forest.
Book Cranwell's Unlimited Golf Package and you can stay in one of the resort's 114 rooms spread between the original manor house and a variety of other "cottages," play unlimited golf, get $20 food credit and have free access to the award-winning spa for swimming and exercise. Midweek rates start at $255.
It's GolfDigest.com policy to never root for rain, but if it does happen, you won't have to sit in the room and sulk. The Norman Rockwell Museum, Massachusetts Museum of Contemporary Art, Edith Wharton and Herman Melville homesteads, Ventfort Hall Museum of the Gilded Age and Tanglewood (the summer home of the Boston Symphony Orchestra) are all within a short drive.
There's even a huge outlet mall one town over, if you're looking for last season's version of the Tiger Woods Nike golf shoe.