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The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).

One&Only Royal Mirage, the calmest and most elegant of Dubai’s mainland beach resorts, consists of three Arabian-styled palace hotels set amid a lush, 65-acre palm garden fronted by a three-quarter-mile white-sand beach. The Palace, the oldest and largest hotel, still has the feeling of an intimate escape despite the past decade’s frenetic high-rise construction along the coastal highway. The Arabian Court draws local couples and, in winter, sheikhs who take trained falcons to tea in the lobby. The most exclusive joint, the Residence, is closest to the spa where guests indulge in massage-themed vacations. All rooms share a French-Moroccan decor and courteous staff who continually offer fruit skewers, cold towels, and drinks around four of the U.A.E’s most beautiful outdoor pools.

The largest luxury hotel in the city, the Charleston Place takes up a full city block with entrances on King and Meeting streets; the latter leads to the grand lobby, with its imperial open-arm staircase, 12-foot crystal chandelier, and Italian marble floors. Its 433 large guest rooms have old-fashioned Southern details like mahogany and damask furnishings. The hotel’s lower level houses fine-dining restaurant Charleston Grill, an attractive hotel bar, a large indoor saltwater pool with a retractable glass roof, and a shopping arcade with designer stores. The hotel recently began a $150 million renovation but will remain open as the property is upgraded from stem to stern.

A historic New York state resort, Mohonk Mountain House first opened in 1869 in the Hudson Valley, about 90 miles from New York City. This Victorian castle has welcomed five U.S. presidents (including Bill Clinton) in addition to countless artists, authors, and actors. Surrounded by thousands of acres of nature, the resort is perched on a cliff overlooking Mohonk Lake. Guests travel specifically for the dramatic, vibrant fall foliage and expertly manicured gardens. Rates are all-inclusive and comprehensive—all meals and activities are included for a single nightly rate. Yoga classes, boating, tennis, horseback riding, and rock climbing are all popular activities. During the winter, ice skating and cross-country skiing lure guests into the great outdoors. Rooms with wood-burning fireplaces and a huge spa with heated indoor and outdoor pool create a peaceful retreat.

The resort Montage Kapalua Bay, perched on an ocean-facing cliff on the island’s northwestern shore, impresses right from the start. The experience begins at the entrance, where tranquil koi ponds set the tone for an impressive array of pools and waterfalls at the center of the 24-acre property. From there, 56 palatial, residence-style villas encourage hunkering down—each is equipped with a kitchen with marble countertops and wine refrigerators; deep-soaking tubs and walk-in showers; and washers and dryers—but do venture out. The concierge can arrange for everything from fishing charters to ziplining. Should you prefer a quieter pursuit, the spa offers a range of tranquil services, including a restorative seaweed cocoon treatment performed in an outdoor pavilion.

Situated on 10 acres in the heart of downtown, this 24-story hotel lives up to its name with 775 elegant guest rooms, appointed with handcrafted cherrywood Richelieu furnishings, floor-to-ceiling windows, Italian marble bathrooms, and spacious balconies. Public outdoor spaces include an immaculately manicured courtyard garden with a central fountain, a pretty-as-can-be terrace café serving house-made breads, and an outsize pool lined with loungers, all against a backdrop of classic white granite. To top it off, the hotel also features a colorful toy store with costumes galore, a jewel box of a sweets shop with macarons and other divine confections, and a men’s haberdashery. The lobby lounge hosts a live jazz band on weekend nights, and the staff tends to a crackling open fire during cool weather.

If you find yourself in Asheville, NC (and you should, as AFAR’s recent feature pointed out - there’s a lot to love in Asheville); stay at The Grove Park Inn. This historic hotel is part art deco/part arts and crafts with rambling porches and a view of the mountains to rival other properties in town. The Horizons restaurant serves up Michelin-worthy meals and their sommelier will not steer you wrong. The spa buried in the depths of the property has salt water pools and heated waterfalls, with trained masseurs who can erase any ill your body is suffering. Rooms are spacious and comfortable with updated bathrooms. The elevator is built into a massive fireplace. It’s an incredible place that does an excellent job of showing off the quirky character of the Southern town it calls home.

This hotel is on our list of The 10 Best Hotels in Canada.

Fogo Island Inn sits at the very edge of the north Atlantic on isolated Fogo Island in Newfoundland. Designed by internationally renowned architect Todd Saunders, the inn’s arresting modern appearance is suggests an iceberg from a distance, with its raised section representing the island’s traditional stilted fishing platforms. But when visitors get close, they see the wooden boards layered together, and it’s clear that everything is handmade. The by-hand ethos covers all the furniture and furnishings, created by local artisans who’ve worked with artists in residence to create contemporary versions of traditional objects.

Staying at the inn is admittedly expensive, but this is essentially a living art piece that supports the local community and aims to honor the island’s past while carrying it to the future. It feels like a grand home with attentive staff. A private 42-seat cinema, partnered with the National Film Board, carries a movie library for guests to enjoy at any time; there’s also an art gallery, a well-stocked library, and a supply of Gore-Tex hiking boots and other outdoor equipment to borrow. The inn shows off the dazzling landscape, and it’s easy to spend all day at the windows watching the sea while whales breech, icebergs float past, or storms dash on the rocks.

There are a handful of appealing options in the West Loop, but the most exciting is the Hoxton Chicago, whose laid-back lobby is filled daily with locals and guests working, meeting, dining, drinking, or hanging out with a coffee. Part of the socially focused Hoxton hotel group that launched in London’s East End in 2006, this 182-room hotel has become the West Loop’s top rendezvous spot for meetings (unless you’re a member of nearby Soho House), but upstairs is just as enticing. We love “Flexy Time,” which allows guests to check in and out whatever time of day they like, so long as they book directly through the hotel website.

Attached to the hip, retro Calistoga Motor Lodge, MoonAcre Spa & Bath welcomes hotel guests and non-guests over 16 years of age to experience its fun and funky spa. If you’re looking for a soak in one of the area’s natural geothermal hot springs, there are three pools to choose from at MoonAcre, as well as facials, scrubs, and massages galore. The Perfectly Muddled treatment takes the town’s famous mud baths—which typically call for spa-goers to submerge themselves in warm, sticky mud—and instead allow guests to apply the exfoliating mud themselves or have the spa attendant do so, making the mud “bath” a more personalized and, honestly, slightly more comfortable experience. For ultra relaxation, try a CBD massage featuring cannabidiol, an extract derived from cannabis. Stop by for Happy Spa Hour between 4-6 p.m. on Wednesdays, or, for frequent visitors, check out the newly launched Spa Club Memberships. MoonAcre is great for groups, too, with plenty of room to enjoy a friends’ getaway weekend. Treatments start at $70.

Both charming and affordable (it doesn’t charge a resort fee), this intimate 37-room property also has an unbeatable central location—near the heart of Old Town and just a few blocks from Duval Street and Mallory Square. Part of the Historic Key West Inns collection, the Key Lime Inn features classic Key West style with a 19th-century main house highlighted by a double-height colonnaded entrance and green shutters. Rooms follow suit with high ceilings and classical proportions, and beds are done up in crisp, white linens; most have sitting areas and private walkouts or porches to encourage lingering. Though short on amenities, the grounds are shaded by tall palms and dotted with Caribbean-style clapboard cottages painted in cheery colors with gingerbread trim, and all offer free WiFi. And if the beach doesn’t call you, a large wood deck surrounds the heated outdoor pool, and hammocks and porch swings are placed around the property for maximum relaxation.

Part of the Grande Lakes resort complex, the Ritz-Carlton Orlando has enough amenities to keep a family happily occupied without ever having to leave the property. Accommodations feature private balconies with garden or lake views and separate tubs and showers, while club-level suites offer snacks and refreshments throughout the day and exclusive activities such as photography lessons with the hotel’s photo concierge, but the rooms aren’t why you came. Cool off at the clover-shaped pool—the lazy river next-door at the JW Marriott is also available—or with a zero-gravity massage, performed while you sway in a hammock in the spa’s rooftop garden. The Greg Norman–designed golf course has a caddie concierge program; kids play free with an adult. Between the two large hotels on the Grande Lakes property, there are a dozen dining options—try Highball & Harvest, where the farm-to-table cuisine is made with local ingredients and served alongside beer from its own nano-brewery. The $35 daily resort fee covers theme-park shuttles, kids’ club activities, daily bike rentals, driving range privileges, and WiFi and phone calls.

Shangri-La’s Boracay Resort & Spa is located in one of the Philippines’ most popular vacation spots. And while it has all the musts—the turquoise waters, the powdered-sugar shores, the lush hills—what it doesn’t have is the crowds. And therein lies the resort’s beauty, or at least some of it. Tucked into an eco-reserve with its own shimmering beach, the Shangri-La is also home to a canopy-cloaked dining aerie, sunset-surveying clifftop cabanas, and a peninsular spa on a private bay. Accommodations are impeccably appointed with local touches (think woven abaca rugs and lamps bedecked with capiz shells), and several of the lodgings feel more like private vacation homes. Take the aptly named treehouse villa, for example, where the canopy-level second story commands stunning sea views (best enjoyed from the hot tub on the balcony), or the pool villas, where the lure of en suite swimming almost overpowers the sea just outside.

With its 26 suites, private beach, and two waterfront bars, Calabash Cove offers a boutique hotel alternative to the typical all-inclusive experience. Set a stone’s throw from the turquoise waves of Bonaire Bay, the sprawling, Balinese-inspired Water’s Edge cottages are the ones to book thanks to private plunge pools, outdoor rain showers, and patio hammocks positioned to highlight superb sunsets. The resort’s remote location ensures tranquility, as does the spa, which offers in-room treatments using ingredients sourced from St. Lucia’s floral and culinary bounty. That abundance is also on display in the Windsong restaurant, where local dishes get an elegant twist (octopus tempura, smoked coconut crème brûlée) in a terrace dining room with the ultimate ocean backdrop. Follow your meal with a brief walk down Calabash Cove’s small boardwalk and stop to spot shooting stars in the dark skies above.

Epic might be an understated description for this collection of thatched-roof bungalows built on stilts over the crystalline waters of the Bora Bora lagoon. This luxury resort is nestled in the dreamiest of settings—wooden walkways link palm-dotted islets fringed with white sand, while the craggy green peaks of Mount Otemanu loom in the distance. Guests can alternate between the beach and the infinity pool, lined with oversized cabanas, or sample activities like stand-up-paddleboard yoga, shark feeding, and snorkeling with the resident marine biologist. Also on offer is a luxurious spa, offering an extensive menu of treatments based on native ingredients like monoï and vanilla. As for the bungalows, Polynesian touches pepper the chic, honey-hued interiors, while indulgent soaking tubs sit beneath shuttered picture windows that open onto the sea. Large decks with swoon-worthy views have stepladders down to the water—a good way to test out the provided snorkeling gear. Airy beachfront villas are also available for those who prefer to stay on land.