With an easygoing ambiance, spectacularly beautiful mountains, deep blue lakes, and evergreen forests, Vermont’s romantic scenery is ideal for a Valentine’s Day getaway. Whether you prefer quiet meals by the warm fireplace or electrifying festivals and outdoor activities, the cities and towns of Vermont provide endless opportunities for unforgettable moments. When you stay at one of many incredible Vermont vacation rentals, you can enjoy easy access to local shops to sample wines and chocolates, enjoy elegant meals, join in on celebrations, and even go skiing. Here are the top Valentine’s Day getaway spots in the state of Vermont.

1. Burlington

The city of Burlington is in a lovely location on the shore of Lake Champlain in northwest Vermont. Valentine’s Day holiday coincides with the city’s annual Vermont Winter Brewfest, where you can enjoy live music and sample craft beer. At the Paint and Sip Studio’s Valentine’s Day Forever Love event, a local artist instructs you on how to create a painting while you sample wine or champagne. Nothing expresses Valentine’s Day like chocolate, and Burlington is the home of Vermont’s premier chocolate establishment, Lake Champlain Chocolates. Take a tour of the sweet-smelling factory while you sample its delicacies. For a sumptuous Valentine’s Day feast at a table near a roaring fireplace, head for Hen of the Wood. If you prefer a more informal dinner, have a burger and a beer at the Farmhouse Tap and Grill.

Find vacation rentals in Burlington

2. Shelburne

The town of Shelburne lies south of Burlington on Lake Champlain, and one of its most charming attractions is the Vermont Teddy Bear Factory and Bear Shop. Indulge your inner child and tour the factory to watch the process of teddy bear creation. Pick up the special Valentine’s Day teddies as gifts for each other. Shelburne Winery hosts an annual Wine and Chocolate Weekend on Valentine’s weekend. This event pairs local wines with chocolate truffles and cheesecakes. At Shelburne Farms, bundle up close to each other and enjoy a romantic horse-drawn sleigh ride over the snow. For your Valentine’s Day dinner, savor a five-course meal in a candle-lit dining room at Rustic Roots.

Find vacation rentals in Shelburne

3. Montpelier

Montpelier, the capital of Vermont, maintains the tradition of the elusive Valentine Phantom. Every year, at some time during the evening of the 13th, unknown individuals or groups decorate public buildings and storefronts with multitudes of red hearts drawn on sheets of paper. If you’re in the mood for Valentine’s Day sweets, where to go in Montpelier is the renowned Skinny Pancake to enjoy a crepe. For more sweet sensations, head for the Morse Farm Maple Sugarworks, tour the sugar house, visit the Vermont farm life museum, and sample the delectable maple syrup products. When you are ready for an elegant Valentine’s Day meal, try Michael’s on the Hill in nearby Waterbury Center, which indeed sits on a lovely rural hill, has large windows so you can enjoy the scenery, and serves an amazing special Valentine’s Day tasting menu.

Find vacation rentals in Montpelier

4. Rutland

Historic Rutland holds an annual Winter Fest over the Valentine’s Day holiday. Your Rutland vacation rental provides easy access to all the Winter Fest fun, which includes community ice skating, night sledding, and an ice sculpture contest. Among other oddball events are a cardboard sled contest and a teddy bear carry obstacle course. There is also an abundance of hot cocoa, toasted marshmallows, and other snacks. The festival closes with a dance for all ages. For your romantic Valentine’s Day dinner, head for Sweet Caroline’s Restaurant in West Rutland, which specializes in slow-roasted prime rib. Alternatively, try Table 24 in downtown Rutland for excellent wine choices along with local specialties cooked over a wood-fired grill.

Find vacation rentals in Rutland

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

5. Waitsfield

The town of Waitsfield in central Vermont is renowned for its proximity to great skiing, and the Mad River Glen ski area offers a special Valentine’s Day Celebration offer for couples so you can hit the slopes together. Where to go in Waitsfield for Valentine’s Day also includes visits to some iconic and eclectic shops. Head for the Mad River Taste Place to enjoy samples of local food and drink products such as cheeses, charcuterie, cider, beer, and wine. For some of the most unusual Valentine’s gifts you’ll ever see, stop in at Mad River Antler and browse through the collection of lamps, chandeliers, candle holders, furniture, and other items made from naturally shed deer and elk antlers. Savor a sublime Valentine’s Day dinner with wine at the Common Man Restaurant in nearby Warren.

Find vacation rentals in Waitsfield

6. Quechee

Your vacation rental in the town of Quechee is in a spectacular setting in Quechee Gorge along the Ottauquechee River, the site of a famous historic covered bridge. Valentine’s Day shopping and sightseeing is a unique experience at Quechee Gorge Village, an amazing rustic collection of establishments that includes the Vermont Antique Mall, the Vermont Toy Museum, and the Green Mountain Fire and Hammer Blacksmith Shop. At the Vermont Spirits Distilling Company, hit the tasting room to sample the renowned locally made vodka, gin, bourbon, and whiskey. The place to go for an unforgettable Valentine’s Day dinner is the Simon Pierce Restaurant at the Mill, which extends out over the river and offers an incomparable view of a waterfall and the covered bridge. Along with the mouth-watering cuisine, you have the opportunity to eat from Simon Pierce’s signature stoneware and glassware.

Find vacation rentals in Quechee

7. Bennington

The historic city of Bennington lies in the southwest corner of Vermont near the border with New York along the western edge of the beautiful Green Mountains. Head for the Village Chocolate Shoppe for the special Valentine’s Day holiday treats of strawberries dipped in white, milk, and dark chocolate. If you crave heart-shaped cookies and tarts, check out the Crazy Russian Girls bakery. At the famous Bennington Publyk House restaurant, sit before a warming fireplace while you feast on a delicious Valentine’s Day meal. The Copper Grouse serves up unique local cuisine, such as cider-brined chicken and cheddar ale soup. Alternatively, enjoy the historic ambiance while you share a meal and a brew at Ye Olde Tavern.

Find vacation rentals in Bennington


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