With its quaint New England villages and bustling cities with small-town charm, Connecticut is an ideal destination for a Valentine Day’s celebration. From romantic cabins to cozy waterfront cottages, there are plenty of unforgettable vacation rentals in Connecticut. Plan a getaway in Connecticut to see and experience the state’s numerous charming attractions and historic landmarks.

1. Madison

The Madison Beach Hotel hosts its Annual Nuptials on Valentine’s Day. This is the perfect opportunity to tie the knot or renew your vows. The elegant ballroom overlooks the waters of the Long Island Sound, and you can enjoy wedding amenities such as a bouquet and boutonniere, cocktail reception for you and eight guests, a four-course dinner for two complete with wedding cupcakes, and a photographer. Once the deed is done, relax and stroll along Main Street for some window shopping, then take a long walk along the town beach. Treat yourself to professional theatrical presentations at the Long Wharf Theater or TheaterWorks in New Haven or swing up to Hartford’s stage company for seasonal entertainment. Spend some cozy time cuddled at a corner table at the Bar Bouchee, the best place in Madison for mussels and sweetbreads.

Find vacation rentals in Madison

2. Mystic

Soak up history as you walk hand-in-hand through the lanes of Historic Downtown Mystic just half a block from the scenic Mystic River. If the weather outside is frightful, spend time at the Mystic Seaport Museum of America and the Sea, or huddle near a fireplace in The Whaler’s Inn while you sip wine and savor a homemade meal. Browse through the 18th century Old Mystick Village and shop for handmade quilts or silver jewelry, then pick up some artisan goodies such as honey and maple syrup for the folks back home.

Find vacation rentals in Mystic

3. Old Saybrook

Explore the scenic waterfront Highway 154 with your loved one around North Cove Road to get a glimpse of beautiful, historic homes and magnificent, stately trees that are hundreds of years old. Snuggle together for a tasty meal at the upscale Fresh Salt restaurant, where fresh seafood reigns supreme, or travel a few miles to the Cafe Routier in Westbrook for a vegetarian-friendly and gluten-free menu in romantic seclusion. Relax in bliss as you delight in a couple’s massage at the Saybrook Point Inn & Spa, then head over to the Katherine Hepburn Cultural Arts Center for a performance or a tour through the museum that honors the legacy of the state’s finest actress.

Find vacation rentals in Old Saybrook

Find the perfect Connecticut vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Greenwich

Greenwich is where to go to find some of the most beautiful homes in New England, so take a tour along the back roads of town to see these beauties set in scenic landscapes on tree-lined lanes. Romance your sweetheart on the Connecticut Wine Trail for an abundance of wine tastings and out-of-this-world sunset views over vineyards such as Sunset Meadows Vineyards and Jones Winery. Before you retire to your romantic getaway, stop for a couple’s massage at The Dream Spa or Spa of Delamar. With over 861 restaurants in Greenwich, your choices are endless, but a very romantic spot in the heart of Greenwich is the Elm Street Oyster House where you can partake in exquisitely prepared pan-fried oyster, or head down to the Elm Street Raw Bar if you prefer your oysters au natural.

Find vacation rentals near Greenwich

5. Essex

If you love to explore the outdoors together, the RiverQuest Winter Wildlife Eagle Cruise is an ideal choice for some together time. During the winter, bald and golden eagles congregate in the lower portions of the Connecticut River, and this cruise gives you up-close-and-personal encounters with these magnificent creatures. You can shop in downtown, a quaint area where you can purchase a piece of unique jewelry at One N Main, or get a cozy couple’s massage at the Spa of Essex. The Griswold Inn, a stately New England home-turned-inn, has been around since 1776, and you can tap your feet to live music in the bar, or browse the memorabilia that lines the walls. Choose a 1776 sausage sample of authentic clam chowder, then dig into seasonal cuisine as well as prime rib, cod, and salmon. Consider the Essex Clipper dinner train for a four-course meal in a restored 1920s Pullman diner pulled by a vintage diesel locomotive. This 2.5-hour excursion takes you through the scenic Connecticut River Valley which is where to go in Essex to find the time to soak up gorgeous landscapes.

Find vacation rentals near Essex

6. Hartford

Valentine’s Day weather in Connecticut may be chilly, but you can spend together time indoors exploring the lives of two famous Americans, Mark Twain and Harriet Beecher Stowe, at adjacent museums. The Mark Twain House and Museum on Farmington Avenue is where Samuel Langhorne Clements lived and worked between 1874 and 1891. This beautiful museum has 19 rooms to explore, chock full of permanent and rotating exhibits. The 5,000-square foot, two-story cottage-style Harriet Beecher Stowe Center, a U.S. National Landmark. celebrates the life of the author of ‘Uncle Tom’s Cabin.” Ms. Stowe lived in this house from 1873 until her death in 1896. Take a stroll along the Mortensen Riverfront where you can shop, relax and watch boats on the water, take a boat tour of the city, or take a walk across Founder’s Bridge. Dance to a live DJ or enjoy cocktails and small plates as you snuggle in the comfortable lounge booths at Nixs Hartford. For a more cozy, romantic dining experience, go to Firebox, a farm-to-table restaurant with warm brick walls lined with art by local talent.

Find vacation rentals near Hartford

7. New Milford

For a truly secluded, quiet, and romantic getaway, New Milford is an oasis of nature, local farms, and country living. Take a drive through Lover’s Leap Park and look at the newly restored, vibrant-red iron bridge that has a beautiful view over the Housatonic River. When the weather’s fine, bring along a picnic lunch and walk along the park’s hiking and walking trails or stroll through the town Green and sit in the gazebo. Explore music, art, cuisine, crafts, and literature held in a collection of historic farm buildings at the Henderson Cultural Center at Hunt Hill. Get a sense of life in Connecticut over 163 years ago as passengers stepped off the train from Bridgeport at the Merwinsville Hotel located in the Gaylordsville section of New Milford. For a cozy, romantic dinner head to La Piccolina, or for a more casual meal stop by the Upper Crust.

Find vacation rentals near New Milford

Ready to go? Check out these amazing Connecticut vacation rentals on Tripping.com.