Romantic Winter Retreats in Connecticut Last Updated: November 2023

When the weather cools down, romance heats up in Connecticut’s hotels, inns, and B&Bs. Whether getting cozy by the fire or enjoying a wintry hike in the woods, we’ve got so many ways to help you make the most of the season together.  Here are just a few of the destinations where you’ll find lodgings, activities, and attractions to help you set the mood. Planning a romantic escape to Connecticut? You'll always find great ideas and getaways here.

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Greenwich Getaway

Enjoy a stay in historic and scenic Greenwich, a gem of a town on Long Island Sound. Easily reached by car or train from New York City, Greenwich is home to museums, galleries, shops and restaurants that are open year-round.

Start with a reservation at one of Greenwich’s luxury accommodations, such as the J House Greenwich or Delamar Greenwich Harbor. Do a little shopping along Greenwich Avenue, then grab takeout at Meli-Melo or enjoy a sit down meal at l'escale. Take a romantic stroll through Greenwich Point Park, or explore the many art and science exhibits in the Bruce Museum.

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Unwind in Woodstock

Connecticut’s northeastern region is known as “the Quiet Corner,” but you’ll still find wonderful signs of life in the smaller towns and villages tucked among rolling hills.

Book a room at Woodstock’s romantic Inn at Woodstock Hill, and be sure to have dinner at the main dining room with a romantic fireplace. Enjoy a wintertime wine tasting at Taylor Brooke Winery, and before handing back, visit Soleil & Suns Bakery for some wonderful homemade artisanal breads and desserts.


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A Romantic Interlude in Lyme

Old Lyme is located close to the Connecticut shoreline. This former artist’s colony is a popular summertime resort, but still has a lot of warmth to offer in winter and lovely places to lodge like the Old Lyme Inn.

If the outdoors beckons, an off-season hike along the beach in Rocky Neck State Park. Visit the Florence Griswold Museum for an enchanting collection of American impressionist art. Or, head down the road to Flanders Fish Market & Restaurant for lunch or dinner.

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Winter on the Water in Niantic

Amazing water views are always in season. So why not break away from the expected and enjoy an off-season stay at the Inn at Harbor Hill & Marina, voted one of the "Top 10 B&Bs" in the USA, and offering many great packages and deals. In the seaside town of Niantic, stop for something sweet at Gumdrops & Lollipops or browse the Book Barn.

Afterwards, enjoy takeout from local farm-to-table bistro La Belle Aurore. Or sample local seafood at any one of a number of places.

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Get Lost in the Litchfield Hills

Along the western edge of Connecticut, the rolling hills of Litchfield County are home to small towns and villages made for romance, indoors and out. You can snuggle in front of a fire at the Manor House in Norfolk, or hike among the springs and streams at Macedonia Brook State Park. Browse for treasures and souvenirs at shops like Company Store Antiques and Rolling River Antiques. And grab a bite at the Fife ‘N Drum Restaurant, a Kent classic. Or drive over to the Hopkins Vineyard in Lake Waramaug, for amazing views, tours and tastings year-round. 

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Mix it Up in Madison

In Madison, a romantic getaway can encompass the best of both worlds—the charm of a small New England Town and, just a short drive away, the culture of a vibrant city.

Set up camp at Madison’s Scranton Seahorse Inn and explore downtown Madison, with its shops, galleries and the famous RJ Julia Bookshop.

The next day, head into New Haven to explore contemporary art at Kehler Liddell Gallery. Savor local history and siip a cocktail at 116 Crown, then devour a slice of Wooster Street’s world- famous pizza at the original Frank Pepe’s. For some extra fun, experience a Taste of New Haven tour with your special someone.


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Discover Colonial Charm in Essex

Explore Essex, a village on the Connecticut River that offers the perfect blend of history, art, shopping, and dining. Browse the Connecticut River Artisans' gallery on Main Street and explore the natural beauty of the region at the Connecticut River Museum. You can even catch one of RiverQuest’s Winter Wildlife Cruises from here. Afterward, warm up and grab a bite at Carlson's Landing.

For a romantic dose of authentic colonial style, check into The Griswold Inn, one of the oldest continuously operating inns in the country. Dine by the fireplace on seasonally inspired cuisine, sip award-winning wines in the Wine Bar or grab a drink in the legendary Tap Room, which was originally built in 1735 as a schoolhouse.

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Make Memories in Morris

Escape to the countryside — the extravagant way. Book a unique, artistically-designed room at Winvian Farm for a getaway you’ll both remember forever.

Nearby, dine at award-winning Arethusa al tavolo in Bantam for chic and delicious farm-to-table New American cuisine.