Luxury guest rooms in Orleans, Massachusetts

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.

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.

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.

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.

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.

Located just a quarter mile from the famous Nauset Beach in Orleans, Massachusetts, the Ship's Knees Inn is a charming and unique lodging option. Housed in a restored sea captain's home dating back to 1820, this inn offers 16 individually appointed guest rooms, 14 of which have private baths. Guests can enjoy daily continental breakfast, an outdoor swimming pool, WiFi, and in-room air conditioning. The innkeepers, Peter and Denise Butcher, are known for their warm hospitality, making guests feel right at home. The beautiful property features rolling green lawns, colorful gardens, and quiet spots to relax. With its close proximity to Nauset Beach, guests can easily spend their days lounging on the sand or exploring the nearby attractions on Cape Cod. Whether you choose to unwind by the fire pit in the evenings or take a dip in the in-ground pool, the Ship's Knees Inn offers a peaceful haven for a memorable beach vacation getaway.