Cozy Hotels, Inns and B&Bs in Fairfield County Last Updated 2/21

As the thermometer drops lower and lower, romance heats up in Fairfield County. Whether cozying up by a crackling fire, venturing out to explore the local color or enjoying a wintry hike in the woods, there are so many places to get away and come together. Here are just a few of the charming destinations where you will find safe-friendly lodgings help set the mood. Planning a romantic escape? Great getaways and wonderful adventures await. Just be sure to check each location before venturing out, as safety requirements may change due to COVID-19.

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Homestead Inn, Greenwich

The Homestead Inn in Greenwich is a luxury boutique hotel that’s a showcase of elegance and refined hospitality. Each room and suite, features a unique style and design, offering impeccable services and amenities to pamper every guest. Resting on lushly manicured acres in the prestigious Belle Haven area of Greenwich, this exquisite hotel and the renowned Thomas Henkelmann Classic French Restaurant are inviting, chic and sumptuous, blending sophisticated character with a modern flair. 

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Stanton House Inn, Greenwich

Stanton House Inn in Greenwich is a boutique bed & breakfast, set in an historic early 1900s mansion designed by Stanford White, offering 20 rooms and suites with luxurious amenities such as fireplaces, whirlpool tubs and private balconies. Lovely gardens and a seasonal swimming pool surround the inn, providing a relaxed and lush setting just a short walk to nearby shops and restaurants on Greenwich Avenue.

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Delamar Greenwich Harbor, Greenwich

Just a few steps from Greenwich Avenue’s fashionable shops and restaurants, The Delamar Greenwich Harbor provides a luxury waterfront escape to those traveling on business or pleasure, with 82 deluxe guest rooms and elegant suites featuring stunning views of the town and harbor. In-house fine dining for breakfast, lunch and dinner at l’escale Restaurant features a tempting menu of seafood, fresh herbs and the distinctive flavors of the Mediterranean, accompanied by an impressive wine list celebrating the south of France. And the award-winning Spa at Delamar offers guests an oasis of relaxation and restoration. Equally as luxurious and thoughtfully appointed is The Delamar Southport.

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Roger Sherman Inn, New Canaan

New Canaan’s famed Roger Sherman Inn provides the quintessential New England experience, offering 15 beautifully-appointed rooms and suites decorated with luxurious modern day amenities yet retaining their old world style. The inn also features six unique dining venues including the Terrace Room, Hunt Room, Wine Room and Upper Terrace for private parties and events, large and small, plus world-class catering.

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Hotel Zero Degrees, Norwalk

There is nothing typical about Hotel Zero Degrees, from its ideal setting in the heart of Norwalk to the picturesque rooftop terrace. This hotter-than-hot spot is designed for travelers who want something truly different, offering sophisticated style and supreme luxury in 96 spacious and modern guest rooms and suites. Galleries throughout the hotel feature extraordinary original works by local artists. The sophisticated Mediterraneo Restaurant serves delectable coastal Mediterranean-style cuisine for a truly exceptional dining experience.

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GrayBarns Inn, Norwalk

Nestled in a quiet Norwalk neighborhood filled with historic homes, boutique hotel GrayBarns is a charming countryside retreat just an hour’s drive from the city. Having served as a stagecoach stop, operated as a 1920s speakeasy and hosted some very famous honeymooners, this historic New England inn has quite a few stories behind its shiplap walls. Charming touches like black rotary phones and twin-bell alarm clocks gently nudge you to stash away your smartphone and get into the nostalgic spirit; but there's enough modern design mixed in to ensure there is no hint of stuffiness (you are going to love the in-floor heated bathrooms, Bose speakers and complimentary minibar treats in all six luxury suites; first floor rooms have fireplaces). Want more pampering? Spa treatments, yoga and personal training are available in your room. 

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Inn at Longshore, Westport

The “Crown Jewel” of Westport, The Inn at Longshore is a beloved setting for locals and visitors alike, offering twelve graciously appointed guestrooms and suites. Whether in town for business, an event or a weekend getaway, the inn is a relaxing, waterfront haven and your launchpad for local excursions in and around Westport.  

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Inn at Fairfield Beach, Fairfield

Retreat to the cozy and comfortable Inn at Fairfield Beach, where each suite and studio features its own unique nautical style and quaint layout. This beautiful, family-owned hotel is located in coastal Fairfield, a town that flawlessly blends New England charm and big city sophistication. Experience the perfect getaway, just across the street from the Connecticut shoreline, where you can go from the comfort of your room to the relaxation of the surf and spray in just moments while being able to access a great downtown area featuring shops, boutiques, and delicious dining spots.

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Surfside Hotel, Stratford

How does a “Boy Meets Girl” story of love, loss, risk and redemption wind up with a weekend getaway you’ll cherish forever? You will have to read that story on their website (it’s worth it!). But suffice it to say that this delightful tale ends (or begins?) at the Surfside Hotel in the Lordship section of Stratford. How does a direct beachfront ground floor room with sliding glass doors and magnificent 180° water views from a walk out private patio sound? And a super-cozy room it is, appointed with Tuft and Needle® beds and a luxurious bathroom with curated amenities, flat-screen Sony® television, SurfPod® communications center, free WiFi, comfy robes and beach towels. Surfside guests can use the Point No Point beach directly in front of the hotel and Russian Beach at the opposite end of the seawall. Getting the idea? You will.