New england retreat in Orleans, Massachusetts

A Little Inn on Pleasant Bay is a charming and romantic boutique Bed & Breakfast located in Orleans, Massachusetts. Winner of the 2023 LuxLife Hospitality Awards for Most Charming Bed & Breakfast in MA, our inn offers guests quintessential European hospitality in an all-American setting. Situated between the historic villages of Chatham and Orleans on Cape Cod, our nine-room inn overlooks the picturesque Pleasant Bay. Each room is named after sailboats that sail the waters of Cape Cod, with a strong New England identity and beautifully designed by interior designer Matthew Yee.

Family House BNB is a charming lodging institution located at 15 Pine Ridge Lane in Orleans, Massachusetts, United States. Our cozy and welcoming bed and breakfast offers a home away from home for guests looking to explore the beautiful Cape Cod area. With comfortable rooms, delicious homemade breakfasts, and a friendly atmosphere, Family House BNB is the perfect choice for a relaxing getaway with your loved ones. Experience true New England hospitality at our lovely establishment.

Summer Breeze Cottage is a charming vacation rental located at 16 Pleasant View Drive in Orleans, Massachusetts, United States. Nestled in a peaceful neighborhood, this cozy cottage offers a relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With its serene surroundings and close proximity to the beach, Summer Breeze Cottage is the perfect place to unwind and enjoy the beauty of Cape Cod. Whether you're looking for a romantic getaway or a fun family vacation, this quaint cottage is the ideal destination for your summer escape. Book your stay at Summer Breeze Cottage and experience the ultimate relaxation in a picturesque setting.