The stretch of Route 7 between Lenox  and Pittsfield  has many low-priced motels. The Wagon Wheel Motel (Rtes. 7 & 20, Lenox, 413/445-4532, www.bestberkshirehotel.com , $45–195) is both cheery and cheesy—some of the rooms actually have heart-shaped whirlpool tubs.
In Great Barrington , The Lantern House Motel (256 Stockbridge Rd., Rte. 7, Great Barrington, 413/528-2350, www.thelanternhousemotel.com , $45–200) has a heated outdoor swimming pool and rustic rooms set back from the road.
The Arbor Rose B&B (8 Yale Hill, Stockbridge, 413/298-4744, $115–185) actually has a rose arbor on the front path that blooms in mid-June. Proprietor Christina Alsop is as laid-back and unfussy as the rooms are overflowing in rich details, including four-poster beds and dramatic window treatments. Full breakfasts include Alsop’s “famous” homemade muffins.
A Federal-style country inn located on ten acres, Windflower Inn (684 S. Egremont Rd., Great Barrington, 413/528-2720, www.windflowerinn.com , $100–225) is one of those special properties where every detail feels plucked from a romance novel. Fires blaze in a stone fireplace in one room, while perennial gardens surround an outdoor swimming pool.
The closest you’ll get to a Norman Rockwell painting is a stay in the Red Lion Inn (30 Main St., Stockbridge, www.redlioninn.com , $95–490), an “olde New England” inn featured in Rockwell’s famous painting of Stockbridge . A wrap-around verandah with rocking chairs provides the perfect setting for an afternoon of reverie, while rooms are simply decorated in period style. For more privacy, the inn owns several detached houses in the block behind. (Pass up the “cat suite,” however, as Wilbur can be a bit temperamental.)
To capture the luxury of the Gilded Age, book yourself at the Blantyre (16 Blantyre Rd., 413/637-3556, www.blantyre.com , $675–1,300), a Tudor-style manor modeled after a Scottish castle. Living rooms are decked out with brocade chairs, dark woods, and fireplaces, while guest rooms feature four-poster beds and sweeping views of the 100-acre grounds. The crisp staff seems to anticipate guests’ needs.