By Stephanie McKeon, COO, Joshua’s Worldwide
Connecticut has a way of making luxury feel effortless. From its coastal towns to its storybook charm, this small state knows how to deliver big. The best hotels in Connecticut blend timeless New England beauty with modern indulgence.
Whether you’re planning a romantic weekend escape, chasing ocean views, craving farm-to-table dining, visiting family, or simply looking for a change of scenery, Connecticut’s luxury hotels offer the perfect mix of comfort, charm, and festive spirit.
At Joshua’s Worldwide, we believe the journey should be as unforgettable as the destination. Our luxury car service connects travelers to Connecticut’s most stunning hotels, providing a seamless, stress-free experience from pickup to check-in. Whether you’re flying in from New York, Boston, or beyond, our chauffeurs ensure every mile feels like part of the vacation. To inspire your next holiday getaway, here are five of Connecticut’s best hotels, each offering its own brand of seasonal sparkle.
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The Graduate Hotel in New Haven, CT
In the heart of Yale University’s campus, The Graduate blends historic academia with bold, boutique design. Its walls tell stories of New Haven’s vibrant culture, while the cozy café and lively bar make it a favorite for both locals and visitors. During December, downtown New Haven sparkles with festive lights, pop-up markets, and winter events that make this city feel like a holiday movie set.
The ‘Thing To Do’:
No visit to New Haven is complete without experiencing its legendary pizza scene, a destination in itself. Often called the pizza capital of America, New Haven is home to the iconic Frank Pepe Pizzeria Napoletana, Sally’s Apizza, and Modern Apizza, each with its own loyal following and century-old recipes.
For travelers who want to taste it all, Joshua’s Worldwide offers custom New Haven Pizza Tours! Private, chauffeur-driven experiences that let you sample the best slices in comfort and style. Skip the parking, skip the lines, and savor every bite of New Haven’s world-famous apizza. With your own dedicated driver and curated itinerary, just arrive, and dine, in comfort with Joshua’s Worldwide. Whether you’re coming from New York City, Bradley International Airport, or just across the state, we’ll handle your transportation. Because you know in the back of a private car or limo… you can eat as much pizza as you want and unbutton your pants in a private car afterwards!
Winvian Farm, Morris, CT
One of Oprah’s favorite spots, nestled in the rolling hills of Litchfield County, Winvian Farm is where luxury meets storybook charm. Spread across 113 acres of meadows and forest, this Relais & Châteaux retreat feels like something out of a fairytale. Each of its 18 uniquely designed cottages tells its own tale. From the whimsical Treehouse to the one-of-a-kind Helicopter Suite, each is worth its own stay. Add in farm-to-table dining and spa treatments that melt away stress, and you’ve found the ultimate hideaway.
The ‘Thing To Do’:
No trip to Winvian is complete without a Litchfield Hills Wine Tour (which we are very familiar with here at Joshua’s Worldwide)! Because who doesn’t’ love the Connecticut Wine Trail? The region is dotted with boutique vineyards and tasting rooms that come alive, especially during the holidays each one offering cozy fireplaces, festive décor, and glasses of small-batch reds and crisp whites that pair perfectly with chilly Connecticut afternoons.
Let Joshua’s Worldwide curate a private countryside escape. From the scenic drive to the tasting-room stops and dinner reservations waiting when you return, we’ll handle every detail. You can just sip, swirl, and savor without a single thought about directions or driving. Because when you’re wine-tasting your way through the Litchfield Hills, it’s always better to have a chauffeur (and maybe a little room in the back seat for the bottles you just had to bring home)!
The Goodwin Hotel, Hartford, CT
For travelers seeking a luxury hotel in Hartford, The Goodwin Hotel blends Gilded Age architecture with modern sophistication in the heart of downtown. Once home to Hartford’s elite, this boutique hotel now delivers a vibrant mix of history and style, think soaring ceilings, velvet accents, and a lobby bar that makes every night feel like an occasion. Steps away from theaters, galleries, and some of the city’s best restaurants, The Goodwin is a perfect base for exploring Connecticut’s capital year-round.
The ‘Thing To Do’:
Hartford is underrated, there is so much to see and do! Start with a show at The Bushnell (and yes, Joshua’s Worldwide can arrange the best seats in the house). Explore the Wadsworth Atheneum, America’s oldest public art museum, or take a leisurely walk through Bushnell Park. In summer, enjoy Riverfest fireworks and live music; in winter, skate under the lights at Winterfest Hartford, a can’t-miss city tradition.
With Joshua’s Worldwide private car service in Hartford, you can turn a busy day of sightseeing or meetings into a seamless experience. From theater drop-offs to dinner reservations and airport transfers, we handle every detail of your travel and transportation.
The Lloyd Hotel, Stamford, CT
For travelers who love modern luxury and convenience, The Lloyd in downtown Stamford delivers both. Sleek, minimalist interiors and personalized service make it one of the most stylish boutique hotels in Connecticut. The Lloyd combines city energy with coastal ease, and it’s steps from some of Connecticut’s best shopping and dining and nightlife.
The ‘Thing To Do’:
There’s plenty to explore year-round here: stroll along the Stamford waterfront, discover the high-end shops and restaurants of Greenwich Avenue, or visit the Stamford Museum & Nature Center for art, animals, and trails in one scenic stop.
And with Joshua’s Worldwide private car service in Stamford, you can move from meetings to cocktails to coastal views without lifting a finger. We offer direct transfers from JFK, LaGuardia, and Westchester, as well as hourly chauffeur services for guests who want to explore on their own schedule!
The Delamar, Westport, CT
Refined and effortlessly elegant, The Delamar Westport embodies everything that makes Connecticut’s shoreline so special. This boutique hotel combines modern design with timeless hospitality. From its waterfront views and award-winning spa to the farm-to-table dining, this spot draws both travelers and locals alike. Each room feels like its own retreat, and the service? Impeccable: the kind you remember long after checkout.
The ‘Thing To Do’:
Spend your day exploring Main Street Westport, where local boutiques and galleries line the charming downtown. Dine at The Whelk or OKO for coastal-inspired cuisine (we’ll handle your reservations) or catch a live show at the Levitt Pavilion or the Westport Country Playhouse. Nearby Compo Beach buzzes with life and in winter, the town glows with that cozy, classic New England charm.
Of course, The Delamar experience doesn’t stop in Westport. The sister properties are located in Mystic, Greenwich, Southport, and West Hartford. Delamar Hotels offer sophisticated stays across Connecticut, each one infused with its own local flavor and luxurious touch. Whether you’re staying seaside or in the heart of a Connecticut city, every Delamar feels like a second home: beautifully designed, elegantly understated, and uniquely Connecticut.
Let Joshua’s Worldwide take care of the journey between them all. From private car service to airport transfers and nights out, our chauffeurs make it simple to experience each destination in comfort and style.
Ready to Experience the Best Hotels in Connecticut?
From coastal retreats to countryside estates, Connecticut proves that luxury and character can go hand in hand. Whether you’re visiting for business, romance, or a weekend escape, these destinations showcase the very best of New England comfort and class.
At Joshua’s Worldwide, we make getting there as effortless as the stay itself. From airport transfers to curated itineraries, our private car and chauffeur services connect you seamlessly to Connecticut’s most exceptional hotels, so your experience begins the moment you step into the car.
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