Top 10 classic and reinvented roadside motels

6. Jupiter Hotel
If the roads take you to the Pacific Northwest, make sure you stay at Jupiter Hotel in Portland, Oregon. This refurbished roadside spot in the city's happening Lower Burnside neighborhood is self-touted as a “cultural boutique hotel" and is the sort of swanked-up 1960s hotel that young travelers love because it’s super cool and won’t break the bank. Set on two floors that back on to an open courtyard with fire pit and bamboo trees, the 80 rooms come with chalkboard doors (good for scrawling notes), and high-tech amenities like Wi-Fi and DVD-players. Rates from $59/night if you check in after midnight.

7. Kate's Lazy Meadow Motel
For jaded New Yorkers in dire need of a bucolic escape, we recommend hitting the road upstate to Kate’s Lazy Meadow Motel in Mount Tremper, near Woodstock in the Catskills. This kitschy-cool, mid-century motor lodge co-owned by B-52’s rocker Kate Pierson comprises eight rooms tricked out with retro décor and design themes ranging from “wacky UFO” to “river-tubing gnome.” Bathrooms boast hotel toiletries snatched by Kate while on tour with the band. Stay in one of the Duplex De-Lux Kitchen Suites (rooms 7 and 8), which feature balconies, spiral staircases leading to loft bedrooms, "Leave-it-to-Beaver" kitchens, and a shared front porch. Then turn up the jets on the 20-person, saltwater Jacuzzi (complete with underwater light show). If you need even more space to party like a rock star, book the motel’s satellite property, the Lazy Cabin, a three-bedroom “love shack” only five miles from the center of Woodstock. Rates start at $155/night on weeknights and $180/night on weekends (with a two-night minimum).

8. Ohio House Motel
Get your kicks at the starting point of historic Route 66, which ran from Chicago to Los Angeles before it was decommissioned in 1985. Located just north of the Chicago River in the trendy River North neighborhood, home to the largest concentration of art galleries outside of Manhattan, the 50-room Ohio House Motel stands out precisely because it hasn’t been subject to the the über-hip makeover that transformed the rest of this downtown Chicago neighborhood. Though the rooms and amenities are strictly no-frills (free cable TV!), this classic mid-century motor lodge can’t be beat for the location, nostalgia factor, and rock-bottom prices (a rarity in the Windy City). Rates start at $100/night.

9. Old Santa Fe Inn
What looks like a fairly ordinary (albeit attractive) adobe-clad motel is actually a surprisingly plush little boutique inn with rooms and suites decorated on par with many of Santa Fe's pricier properties. You save money here because the Old Santa Fe Inn is relatively small and lacks a restaurant, pool, or other facilities found at some larger hotels, but the rooms are delightful and spotless, done up with top-notch bedding and rustic yet refined Southwestern furnishings; many have working fireplaces, hot tubs, and balconies.

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The location is another plus: It’s located in the funky Guadalupe District, an up-and-coming neighborhood full of galleries, design shops, and offbeat restaurants just a 10-minute walk from Santa Fe's historic Plaza. The continental breakfast here is unusually good, completely with a do-it-yourself breakfast burrito station. Rates start at $150/night.

10. WigWam Motel
For the ultimate in kitsch on Route 66, we recommend camping out in one of the 15 concrete (indeed, you won't find buffalo skins here) teepees at the WigWam Motel in Holbrook, Arizona. This relic from the Mother Road's glory days is listed on the National Register of Historic Places and offers utterly unique accommodations around a parking lot dotted with vintage cars that add to the time-warp effect. While the rooms are decidedly basic (and its beds somewhat lumpy), this slice of Americana is worth sleeping in for bragging rights alone as you make your way to iconic Route 66 attractions like the Petrified Forest National Park and Painted Desert. Rates from $48/night.

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