Resort dining in Orleans, Massachusetts

Located in the picturesque town of Harwich, Massachusetts, the Winstead Inn And Beach Resort offers a truly unique Cape Cod vacation experience. With two properties to choose from, guests can enjoy the charm of the inn in Harwich Center or the beachfront resort in Harwich Port. The Winstead Inn features elegant rooms individually decorated for a luxurious stay, with amenities such as a swimming pool, beautiful grounds, and a spacious great room. Guests can also take advantage of the private beach at the Beach Resort, just a short shuttle ride away.

Pleasant Bay Village Resort is a charming lodging institution located at 1191 Orleans Road in the picturesque town of Chatham, Massachusetts, United States. Situated near the stunning Pleasant Bay, this resort offers guests a peaceful and serene retreat surrounded by natural beauty. The resort features comfortable accommodations, including cozy cottages and well-appointed guest rooms, perfect for a relaxing getaway. Guests can enjoy amenities such as a swimming pool, tennis courts, and a delicious on-site restaurant. Whether you're looking for a romantic escape or a family vacation, Pleasant Bay Village Resort provides a tranquil and idyllic setting for your stay in Cape Cod.

By The Sea Guests is a charming lodging institution located at 57 Chase Avenue in Dennis, Massachusetts, United States. Nestled on the beach, our guest rooms offer one or two beds, private bathrooms, TVs, and mini fridges, with most rooms boasting oceanfront or partial ocean views. With 12 guest rooms in the inn, guests can enjoy a comfortable stay with breakfast included seasonally from May through October. For those seeking more space and amenities, our Suites feature open-concept layouts with full kitchens, living rooms, private bathrooms, and private decks or balconies with side partial ocean views. We offer three one-bedroom suites and two two-bedroom suites, perfect for families or larger groups. Breakfast is not included but can be purchased during peak season.

Rock Harbor Village Co is a charming institution located at 9 Main Street in Orleans, Massachusetts. This cozy village offers a unique blend of shops, restaurants, and services, making it a popular destination for both locals and tourists alike. With its picturesque surroundings and friendly atmosphere, Rock Harbor Village Co is the perfect place to shop, dine, and relax in the heart of Cape Cod. Visit us today and experience all that we have to offer!