Is there any better place to snuggle with your valentine than on Cape Cod in the winter? Cold days and even colder nights, snow-covered beaches, stone gray skies, and heart shaped boxes of chocolates are best enjoyed when spent inside our New England Vacation Rentals holiday hideaways. Offering cozy rooms that stay warm against the cold, fireplaces that add romance to your visit, and more than a few hot tubs bubbling merrily on decks, fighting that cold with hot bubbling waters and this guide to spending your Cape Cod Valentine’s Day getaway in our romantic retreats may help you discover your new holiday tradition.
Bundle Up and Stroll on the Beach
The beaches of Cape Cod are romantic no matter what time of year, and if you have discovered that winter on the Cape is one of the most beautiful times of the year, you’re going to want to spend some time exploring its charms on Valentine’s Day. Night arrives quickly in February, so a sunset stroll (sunset is approximately at 5:15 PM) will still give you plenty of time to make your 6 or 7 PM reservation at whichever restaurant you choose.

Dinner at Chillingsworth, 2449 Main Street in Brewster
We celebrate Valentine’s Day on Cape Cod pretty much the same way people do all over the world, with one main exception, we’re doing it on Cape Cod, one of the most beautiful places in the world! With that being said, a romantic meal is always the highlight of our celebrations, and in Brewster the most romantic of all restaurants would be Chillingsworth Restaurant, offering mouthwatering prix fixe French meals that are served from the kitchen of a centuries old estate.
Valentine’s Day Dinner Ride Train Ride, Cape Cod Central Railroad, 252 Main Street in Hyannis

When you want to up the romance factor, a train ride through a snow covered landscape does so with charm and style. The Cape Cod Central Railroad was once used for transporting passengers and supplies from town to town, but today it offers scenic rides, special events, and its Valentine’s Day Train Ride. The vintage train cars you ride in add an extra layer of special to the romantic ride and the five-course meal brings a delectable shine to your holiday celebration.
Browse Our Valentine’s Day Rentals Here!
Fall in Love all Over Again at Home in Our Romantic Retreats
Our New England Vacation Rentals cozy cottages will make you fall in love with your Valentine all over again. Reserve your favorite today!