TOP 30 Unique vacations 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.

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.

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.

Rock Harbor Village Co is a charming institution located at 9 Main Street in Orleans, Massachusetts. This cozy village offers a unique blend of shops, restaurants, and services, making it a popular destination for both locals and tourists alike. With its picturesque surroundings and friendly atmosphere, Rock Harbor Village Co is the perfect place to shop, dine, and relax in the heart of Cape Cod. Visit us today and experience all that we have to offer!

Captain's Walk is a premier real estate and travel agency located at 82 Captain Linnell Road in the charming town of Orleans, Massachusetts. Specializing in luxury properties and unforgettable travel experiences, Captain's Walk offers unparalleled service and expertise to help you find your dream home or plan the perfect getaway. Whether you're looking to buy or sell a property, or seeking a unique travel adventure, Captain's Walk is dedicated to providing exceptional service and personalized attention to meet all of your needs. Visit us today and let us help you navigate your next real estate or travel journey with ease and confidence.

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.

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.