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It’s no doubt that Dennis Port is a top summertime destination. Set on Cape Cod’s peninsula of quaint beachside villages, this area is picturesque in winter as well. Head to Cape Cod when the tourism season is low and enjoy this charming area without battling the crowds. Be sure to pack some layers so you can get out and enjoy some awesome things to do in Dennis Port in the Winter!


It may be cold outside, but the fish are still biting! Book a fishing expedition with one of the many boat charters in the area and spend a day at sea. Knowledgeable Captains and guides will help you locate the best spots to land a trophy fish. The pristine Cape Cod waters are beautiful year-round, and the area has a wealth of top-notch fishing charter companies. Cook your fresh catch back at your vacation rental and enjoy a romantic dinner by the fire, it’s definitely one of the best things to do in Dennis Port in the Winter!


Take a dip in the Rainbow Falls pool at Cape Codder Resort & Spa in Hyannis; open year-round and available to the public. Close your eyes and soak in the warmth in this outdoor heated pool. With the sound of the waterfall and the warmth of the saltwater, you will feel like you’re in a tropical paradise. In the evening, LED lights in and around the pool create a colorful ambiance.

Cape Cod Rail Trail

Traveling through State Parks, National Parks, and six Cape Cod towns, and winding its way 22 miles across the peninsula, the Cape Cod Rail Trail is a haven for walkers, joggers, bikers and cross-country skiers. The trailhead begins in South Dennis and meanders up past the National Seashore to South Wellfleet. If there’s fresh snow while you’re in Dennis Port, this is a great location for strapping on a pair of cross country skis and working up a sweat along the trail. When the trail is clear of snow, lace up and head out on a walk, run, or bike ride, stopping to enjoy the views along the way. This is one of the most enjoyable things to do in Dennis Port in the Winter!

Book a Stay to Enjoy these Amazing things to Do in Dennis Port in the Winter

At New England Vacation Rentals, we specialize in vacation rentals on Cape Cod and have over 140 vacation homes available for rent. Whether you’re looking for something with a cozy fireplace or a sweeping ocean view, our rentals are equipped with many perks and amenities. Please contact us at 508-432-0900 or via email at bookings@newenglandvacationrentals.com to make your vacation rental booking. Start planning your Cape Cod getaway today!