I Took My Pups on the Coziest Connecticut Getaway—And It Felt Like a Hallmark Movie

As a Connecticut native, I’ve always loved discovering under-the-radar, cozy getaways that feel like a true escape without requiring a long drive. That’s why I was eager to experience The Kent Collection in Kent, Connecticut. Nestled in the heart of this storybook town, the Collection offers locals and visitors alike a charming blend of accommodations, each with its own personality. There’s The Firefly Inn (which exudes major Gilmore Girls vibes), The Victorian, and The Garden Cottages. Within the cottages, you’ll find The Bunk House, The Little House, and The Train Car—a refurbished 1800s baggage car.

I visited the property around the holidays with my mom and pups, and it turned out to be a dreamy weekend straight out of a Hallmark film. Here's everything we loved about our stay to hopefully inspire your own.

This Storybook Connecticut Stay Feels Straight Out of Gilmore Girls (Yes, There’s Coffee and Cinnamon Rolls)

We stayed in The Bunk House, which was decked out in everything we could ever want in a home-away-from-home, including an open-concept kitchen for slow mornings, a fireplace that was perfect for curling up with a good read, and little luxuries that made it feel both rustic and elevated. We spent a lot of our time in our cozies simply enjoying the space—cooking, relaxing, streaming holiday music and films, and soaking up that cozy cottage energy.

One of the best parts? Kent Collection is just steps from downtown, so when you feel like exploring, everything is right outside your door. And, if you’re anything like me, you love establishing the perfect balance between exploring and relaxing. So, one morning, we grabbed warm cinnamon rolls and coffee by the roaring fire at Wilson’s by High Watch before hiking at Kent Falls State Park. The park is a short drive away and the ultimate way to enjoy some fresh air, sunshine, and views before retreating back to the warm cottage.

We also spent some time perusing the local boutiques, where I grabbed a few unique reads to bring back to the cottage—along with some to wrap for holiday gifts. (The pups, of course, came along for the fun and totally loved cruising through downtown in their puppy stroller!)

While in town, you absolutely cannot skip 45 on Main, home to the best hot cocoa I’ve ever had. The shop’s “luxury” hot chocolate lineup is worth the stop (think flavors like gingerbread, toasted marshmallow, and Nutella). I went with the toasted marshmallow, which was garnished with an oversized roasted marshmallow and fresh whipped cream. 45 on Main also serves up an assortment of homemade chocolates and local ice cream.

And for a cozy night in, we enjoyed stocking up on wine and snacks from 109 Cheese & Wine, which made for the ideal fireside setup, complete with streaming chick-flicks.

Some of my favorite moments were the simplest, no-fuss ones—curling up by the fire with a glass of red, snacking on charcuterie, and unwinding with my sweet little pups nearby. At night, we took advantage of the outdoor fire pits, which made everything feel even more tucked-away and peaceful.

While Kent is particularly magical in the winter, this destination is absolutely worth visiting year-round—whether leaf peeping and wine tasting in the fall, hiking in the spring, or simply craving a serene reset in the summer. 

Pro tip? If you plan to stay at Kent Collection, bring your partner—or make it a girls’ getaway—and don’t forget your pup. The pet-friendly cottages make it easy to turn the whole trip into a cozy little pup-cation.