TOP 30 Romantic getaway packages in Orleans, Massachusetts

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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.

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.

Pie's Cottage is a cozy lodging located at 7 Ellerslie Road in the charming town of Orleans, Massachusetts. This quaint cottage offers a peaceful retreat for guests looking to relax and unwind on Cape Cod. Nestled in a serene neighborhood, Pie's Cottage provides comfortable accommodations and a warm, welcoming atmosphere. Whether you're exploring the nearby beaches, shopping in town, or simply enjoying a quiet evening in, Pie's Cottage is the perfect home away from home during your visit to the United States.

Travel Specialists Inc is a renowned travel agency located at 82 Massachusetts 6A in Orleans, Massachusetts. With a team of experienced travel specialists, we provide personalized and expert assistance to help clients plan their dream vacations. Whether it's a relaxing beach getaway, an adventurous hiking trip, or a romantic European tour, we strive to create unforgettable travel experiences for our clients. Contact us today to start planning your next adventure with Travel Specialists Inc.

Weekend is a stylish clothing store located at 217 Main Street in Orleans, Massachusetts. Curated by Mari Porcari, this upscale lifestyle boutique offers a carefully selected collection of items that are sure to delight and inspire. From small keepsakes to stunning textiles, Weekend has that special piece you've been searching for. Whether you're looking for a new summer dress or a unique accessory, you'll find it at Weekend. Conveniently situated on the way to Nauset Beach, Weekend is a must-visit destination for fashion-forward individuals in the area.

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.