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For most of the past decade, I've been spending more than 100 nights a year in hotels across all six inhabited continents. While most tend to fade from memory in the weeks after checkout, a select few stand out every year to the point where, if I'm planning to return to the given city, I know exactly where I want to stay. While there are some general rules (Japanese hotels have the best breakfast buffets, Caribbean resorts are the most welcoming, etc.), it's often the small things, like a yoga mat in the closet, a portable Bluetooth speaker, a Nespresso machine over Keurig, and dining options as good as any in town, that make me remember hotels years after checkout.
So from hipster Brooklyn to bucolic New England, here are 10 hotels I recommend most and why.
The Homestead Madison (Madison, Connecticut)
Why I love it: The two-story Homestead Madison represents the quintessential coastal New England experience. Sure, there are beachfront hotels with better views. But the Homestead has little touches that most five-star resorts haven’t gotten around to thinking of.
Each room has a fireplace and a record player, on which you can play your choice from the collection of more than 100 vinyl classics in the lounge area. Guests also have access to the Nespresso and popcorn machines in the kitchen. The property is a mile from the train station, and thanks to the bikes, those without a car will still have easy access to the quaint downtown area and the beach.
Best time to go: May to September
The Oaks Waterfront Hotel (Easton, Maryland)
Why I love it: As someone who spent years overpaying for mediocre, outdated rooms in Ocean City, Maryland, and at the Delaware Beaches, The Oaks Waterfront Hotel feels like the laid-back Maryland I wish I had discovered 20 years ago. The 2025 Historic Hotels of America inductee is set against the serene waters of Oak Creek, with The Oak Room Restaurant & Bar's main dining room facing the dock. While the menu changes somewhat frequently, as Easton is on Chesapeake Bay's Eastern Shore, you'll be safe with any Maryland crab dishes.
Speaking of the dock, what makes The Oaks special, in addition to the spacious, unpretentious rooms, is the 40-foot Hinckley Picnic Boat that you can hop aboard for a sunset cruise. You should also take the free shuttle to nearby St. Michaels, also known as "the town that fooled the British."
Best time to go: Spring or fall
The Otesaga Resort Hotel (Cooperstown, New York)
Why I love it: Dating back to 1909, The Otesaga Resort Hotel feels exclusive without keeping up with every technological and architectural innovation. If you grew up loving baseball, knowing that every baseball legend of the past 100 years, from Babe Ruth to Willie Mays, has stayed here is enough. It's still the go-to accommodation for baseball's most celebrated legends during Hall of Fame weekend. The Otesaga Resort Hotel abuts Otsego Lake, which resembles one of the Finger Lakes and is a short walk to Main Street, where nearly every shop has baseball memorabilia that seems more abundant than what's privately owned in any other state, let alone a town of 1,800. It's also a bonus that the Otesaga's sports bar and upscale steakhouse have food options that rival anything you'll get on Main Street.
Best time to go: During baseball season (except for Hall of Fame weekend)
The Ritz-Carlton Orlando, Grande Lakes
Why I love it: The JW Marriott and Ritz-Carlton Orlando, Grande Lakes are adjoined on the same 500-acre property that was once cattle land. There's a shuttle to the theme parks included in your resort fee. But there's enough to do between the two properties to make the theme parks an afterthought, unless you're traveling with children.
You can move back and forth between two of Marriott's top ultra-luxury brands, which share a 40,000-square-foot spa. The more family-friendly JW has a waterpark and a Tuscan-inspired restaurant, Primo, which has creative pasta dishes and pizza options that aren't quite traditional Neapolitan but still work. But the Ritz-Carlton is the more laid-back and luxurious of the two. The 14th-floor Club Lounge with views of the pools below is an essential part of the experience. And the food there goes beyond the simple light bites you'll find in most hotel club lounges.
Best time to go: Year-round, unless you're averse to summer heat or holiday crowds.
The William Vale (Brooklyn, New York)
Why I love it: Yes, NYC's most iconic hotels are in Manhattan. But that doesn't mean that's where all of the best hotels are. Brooklyn's William Vale has everything there is to love about New York, yet the rooms are modern and larger than many NYC apartments.
During the summer months, the fourth-floor 80-degree outdoor pool is as festive as any along the South Florida coast. In the back, there's a more secluded area with sauna barrels, a Midtown view, and private hot tubs for rent. Westlight is the 22nd-floor rooftop bar with 360-degree views of Manhattan, Brooklyn, and Queens. While the Westlight's light bites are good by rooftop bar standards, the ground-floor Southern Italian restaurant, Leuca, is the property's culinary star and has al-dente pasta dishes so delicious that you should not consider dining off-property until you've tried every single one of them.
Best time to go: There’s something to love about New York every month, but stick to summer if you want to enjoy the pool.
Fairmont Pacific Rim (Vancouver, British Columbia)
Why I love it: This is, hands down, my favorite downtown hotel in a densely populated city. Being less than a five-minute walk from the cruise terminal and the SkyTrain, it's an ideal base from which you can explore Vancouver and neighboring cities like Richmond and Surrey. But it's also the small things that go a long way here.
While I expect a Nespresso machine in a five-star hotel, rooms at the Fairmont Pacific Rim also include a milk steamer for the 2% milk in the refrigerator. Rooms include yoga mats, and you can book personal training sessions at the gym, which has machines you won't even find at Planet Fitness. Floors 20-22 are the Fairmont Gold rooms, which include access to the lounge where you can watch seaplanes take off from the harbor while cruise ships glide through. Those rooms also include portable lightning and Type-C charging cables for your smart devices.
Best time to go: Peak cruise season is July and August. Visiting in May, June, or September will allow you to enjoy the outdoor pool without having to pay top dollar.
Tokachigawa Onsen Daiichi Hotel (Hokkaido, Japan)
Why I love it: Japan has one of Asia's highest urbanization rates. But you'd never guess that while soaking in your room's onsen tub while gazing at the Tokachi Chuo Bridge over its namesake river. The culinary highlight is donning a traditional Japanese robe and enjoying sushi and steak that you'll cook to your liking on your own mini grill. Like most higher-end Japanese hotels, the Tokachigawa Onsen Daiichi Hotel takes the breakfast buffet seriously. You can expect plenty of fish, both raw and cooked, but also fresh mozzarella that rivals anything you can get on Mulberry Street or Arthur Avenue. There's also a small market that sells Japan's most internationally famous chocolate (Royce') and baked goods, which you can watch being prepared right around the corner.
Best time to go: April or May for cherry blossoms
Park Hyatt St. Kitts Christophe Harbour
Why I love it: There are enough activities and dining options that you don't have to leave the resort. And while that's not uncommon in the Caribbean, the Park Hyatt's location halfway between the capital cities of St. Kitts and Nevis (two islands, one country) makes this an ideal base. More than a third of the rooms here are suites, some of which have private plunge pools high enough to overlook the Caribbean and neighboring Nevis. From the property, you can book a ferry to Nevis or a tour of the capital, Basseterre.
The most unique activities include morning yoga inside a sugar mill and evening stargazing with a professional. Meanwhile, if you enjoy Caribbean lobster, the seafood buffet in a hut over Banana Bay on Saturday nights is worth planning your trip around. But the best hands-on culinary experience is the cooking demo, where you'll have the chance to make your own coconut dumplings, widely considered the country's national dish.
Best time to go: February to May (June if you want to attend St. Kitts Music Festival)
Andaz Peninsula Papagayo Resort, Costa Rica, by Hyatt
Why I love it: You can easily spend a week exploring this 28-acre property, with its own bikeshare program, sports park, and barista class. There are two separate gyms, one indoor and an outdoor micro version above the spa. Speaking of which, even if you're not in the habit of getting foot massages, the ONDA Spa should be the one exception. That's because there's a good chance that while your massage therapist is helping lower your cortisol, you'll be able to watch monkeys swing from branch to branch high above the outdoor hot tub and cold plunge. It's also fun to eat your way around Latin America at the open-air Chao Pescao and decide which country has the best food on the menu.
Best time to go: December to April (dry season). You might save a bit by booking during the last half of November.
Lovango Resort & Beach Club, St. John
Why I love it: This is the first private island resort in the U.S. Virgin Islands. While the term 'private island resort' may conjure up images of well-dressed jetsetters wearing watches worth more than your car, Lovango is so unpretentious that you can pack only swim trunks, sandals, and a t-shirt and not feel out of place here. With just 31 rooms that you'll need the golf carts to get to and from, you're going to run into some of the same people. On live music nights, communal tables are set up for dining. Speaking of dining, nearly every table is close enough to the turquoise Caribbean waters that you'll feel the ocean breeze and taste the saltwater in the air. While Lovango does have a wood-fired pizza oven, it's the seafood you'll remember most. Sunday is Caribbean buffet night.
Best time to go: February to April is ideal. The resort closes in mid-July and reopens in December.