TOP 30 Charming holiday homes in Chatham, Massachusetts

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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.

Eider Duck Cottages is a charming lodging institution located at 1470 Main Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a tranquil setting, these cozy cottages offer a perfect retreat for those seeking a peaceful and relaxing getaway. Each cottage is beautifully decorated and equipped with all the modern amenities to ensure a comfortable stay. Guests can enjoy the serene surroundings, explore the nearby attractions, or simply unwind on the porch and take in the breathtaking views. Eider Duck Cottages is the ideal destination for a memorable vacation on Cape Cod.

Pine Shore Cottages is a charming lodging destination located at 1370 Main Street in the picturesque town of Chatham, Massachusetts. Nestled among the pine trees, this cozy retreat offers a peaceful and relaxing atmosphere for guests to enjoy. As both a lodging and real estate agency, Pine Shore Cottages provides comfortable accommodations for travelers looking to experience the beauty of Cape Cod, as well as opportunities for those interested in purchasing a vacation home in this desirable location. With a dedicated team of professionals, Pine Shore Cottages also doubles as a travel agency, helping guests plan their perfect getaway to this idyllic seaside town. Experience the tranquility and beauty of Chatham at Pine Shore Cottages.