TOP 30 Massachusetts historic homes in Orleans, Massachusetts

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Located at 29 Main Street in Orleans, Massachusetts, WeNeedaVacation.com is a premier institution offering lodging, real estate, and travel services. Specializing in vacation rentals on Cape Cod, Martha's Vineyard, and Nantucket since 1997, we provide a wide range of options for travelers looking to explore the beautiful beaches, natural landscapes, and unique history of these iconic destinations. From historic Plymouth to the tip of Provincetown, the Cape offers an unparalleled combination of beauty and fun activities. Martha's Vineyard Island boasts six charming towns and 110 square miles of natural beauty, while Nantucket features a preserved main town surrounded by picturesque seaside communities. We offer flexible-length plans with no hidden fees or commissions, guaranteeing booking results and providing personalized services and resources for our members. As the go-to rental site for the Cape & Islands, WeNeedaVacation.com ensures a memorable and stress-free vacation experience. For added protection, travelers can also obtain instant travel insurance quotes through our website.

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.

The Nauset House Inn is a charming lodging establishment located at 143 Beach Road in Orleans, Massachusetts. Nestled in a picturesque coastal town, this inn offers a cozy and welcoming atmosphere for guests looking to relax and unwind. With comfortable accommodations, friendly staff, and a convenient location near the beach, The Nauset House Inn is the perfect destination for a relaxing getaway on Cape Cod. Whether you're looking to explore the local shops and restaurants or simply enjoy the natural beauty of the area, this charming inn provides the perfect home base for your vacation. Experience the warmth and hospitality of The Nauset House Inn during your next visit to the United States.

Kinlin Grover Vacation Rentals is a reputable real estate and travel agency located at 55 Main Street in Orleans, Massachusetts. With a strong focus on providing top-notch vacation rental services, Kinlin Grover offers a wide range of luxurious properties for visitors looking to experience the beauty of Cape Cod. Whether you're planning a romantic getaway or a family vacation, their experienced team is dedicated to helping you find the perfect rental that suits your needs and preferences. From beachfront cottages to charming historic homes, Kinlin Grover Vacation Rentals has something for everyone. Experience the ultimate vacation on Cape Cod with Kinlin Grover Vacation Rentals.

Nauset Rental is a real estate and travel agency located at 3 Main Street in Eastham, Massachusetts. Specializing in Lower and Mid Cape Rentals in towns such as Orleans, Chatham, Harwich, Brewster, and Dennis, Nauset Rental offers secure online payments, damage and travel insurance, and is locally owned and operated with proper licensing and insurance. Guests have raved about their experiences staying at Nauset Rental properties, praising the lovely houses and locations, short walks to beautiful beaches, and amenities such as games and music systems. The owner, Kent, has been described as a joy to work with, accommodating last-minute bookings and even welcoming guests with pets. The properties offer private beach access, stunning views, and a quiet, secluded neighborhood close to activities.

Nauset Rental is a real estate and travel agency located at 56 Main Street in Orleans, Massachusetts. Specializing in Lower and Mid Cape Rentals in towns such as Orleans, Chatham, Harwich, Brewster, and Dennis, Nauset Rental offers secure online payments, damage and travel insurance, and is locally owned and operated with proper licensing and insurance. Guests have raved about their experiences at Nauset Rental properties, praising the beautiful locations, amenities such as games and music systems, and the excellent customer service provided by owner Kent. With private beach access and stunning views, guests have enjoyed the peaceful and secluded atmosphere of the neighborhoods while still being close to activities and attractions.

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.