Luxury inn stay 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.

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.

Orleans Waterfront Inn & Restaurant is a charming establishment located in the picturesque town of Orleans, Massachusetts. Situated right on the waterfront at 3 Old County Road, this institution offers a unique combination of bar, food, lodging, and restaurant services. Guests can enjoy stunning views of the water while dining on fresh seafood and other delicious dishes prepared by talented chefs. The cozy inn provides comfortable accommodations for those looking to extend their stay and explore the beautiful Cape Cod area.

Nauset Beach Inn is a charming lodging establishment located at 237 Beach Road in Orleans, Massachusetts. Situated just a short walk away from the picturesque Nauset Beach, this inn offers cozy and comfortable accommodations for visitors looking to enjoy a relaxing getaway on Cape Cod. With its convenient location, guests can easily explore the nearby attractions, shops, and restaurants. The inn provides a warm and welcoming atmosphere, making it the perfect place to unwind after a day of beachcombing or sightseeing. Whether you're looking for a romantic escape or a family vacation, Nauset Beach Inn is the ideal choice for your stay in Orleans.

The Inn at the Oaks is a charming 13 room Inn located in Cape Cod's historic Eastham, Massachusetts. Our spacious and light-filled accommodations, delicious continental breakfasts, and attention to detail ensure that your Cape Cod vacation will be unforgettable. Situated across from the National Seashore Visitor Center and close to world-famous beaches, the Cape Cod Rail Trail, and historic towns like Chatham, Orleans, Wellfleet, and Provincetown, the Inn offers a perfect location for exploring the best of Old Cape Cod. Many guests consider the Inn their "home" on the Cape and return year after year. Children over the age of 10 are welcome, but please note that our property is not wheelchair accessible. Book 3 nights or more mid-week from March 1 to April 30 and save 10% on your entire stay when booking directly with the Inn using the code SPRING10. Come and experience the beauty and charm of Cape Cod at the Inn at the Oaks.

The Parsonage Inn, located at 202 Main Street in Orleans, Massachusetts, is a historic 250-year-old home offering a unique and charming getaway in East Orleans. Originally used as a Parsonage for the local church in the 19th Century, The Parsonage now provides a blend of historic charm and modern comforts for vacationers visiting Cape Cod. The institution offers a variety of accommodation options to suit different needs, including a cozy three-bedroom cottage and a spacious seven-bedroom house with ensuite bathrooms, designer kitchen, and landscaped garden with a hot tub. Guests can also book one of the four guest bedrooms for a relaxing stay during the shoulder seasons.

Welcome to An English Garden Bed & Breakfast, located at 32 Inman Road in Dennis, Massachusetts, United States. Our charming lodging institution offers a cozy and comfortable stay for guests looking to relax and unwind on Cape Cod. In the main inn, we have 9 guest rooms, each featuring a queen bed, private bathroom, climate control, and TV. Guests can enjoy the ocean views from their private balconies or decks, with some rooms overlooking our beautiful gardens in full bloom during late spring and early summer. Children under 8 years old are not allowed in guest rooms, which are accessible via stairs and sleep two guests comfortably. Complimentary breakfast is served in season from May to October.

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.

Kent's Point is a picturesque park and tourist attraction located at 40 Keziahs Lane in Orleans, Massachusetts, United States. Situated in a peaceful and natural setting, this institution offers visitors a chance to explore the beauty of Cape Cod's landscape. With walking trails, scenic views, and opportunities for birdwatching, Kent's Point is the perfect destination for nature lovers and outdoor enthusiasts. Whether you're looking to relax and unwind or embark on an adventure, this hidden gem is sure to captivate and inspire all who visit.