TOP 10 Luxury vacation accommodations in Orleans, Massachusetts

Lake Farm Boarding Kennels is a premier pet boarding facility located in the picturesque town of Orleans, Massachusetts. Situated at 53 Finlay Road, our institution offers top-notch care and accommodations for your furry friends while you are away. Our experienced staff provides personalized attention to each pet, ensuring they feel comfortable and loved during their stay. With spacious outdoor play areas, cozy sleeping quarters, and a variety of amenities, Lake Farm Boarding Kennels is the perfect home away from home for your beloved pets. Visit us today and see why we are the leading choice for pet boarding in the United States.

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.

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.

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.

Cape Cod Skaket Beach Waterfront Rental is a premier real estate and travel agency located at 193 Skaket Beach Road in Orleans, Massachusetts. Offering exquisite waterfront rental properties with stunning views of Skaket Beach, this institution specializes in providing luxurious accommodations for those looking to experience the beauty of Cape Cod. Whether you're seeking a relaxing beach getaway or a fun-filled family vacation, Cape Cod Skaket Beach Waterfront Rental has the perfect rental for you. Book your stay today and enjoy a truly unforgettable experience on the shores of Cape Cod.

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.

Ocean Front Cottage is a charming accommodation located on Wildflower Lane in the picturesque town of Orleans, Massachusetts. This cozy cottage offers stunning views of the ocean, providing guests with a peaceful and tranquil retreat. The cottage is beautifully furnished and equipped with all the amenities needed for a comfortable stay. Guests can relax on the private patio, take a leisurely stroll along the beach, or explore the nearby shops and restaurants. Whether you're looking for a romantic getaway or a family vacation, Ocean Front Cottage is the perfect destination for a memorable stay by the sea.