TOP 20 Best Luxury vacation rentals in Wellfleet, Massachusetts

The Colony of Wellfleet is a unique lodging institution located at 640 Chequessett Neck Road in Wellfleet, Massachusetts, United States. Originally designed and built in 1948 by architects Nathaniel Saltonstall and Oliver P. Morton, this institution was known as the Mayo Hill Colony Club, serving as a private club and art gallery for artists and patrons. In 1963, Loris and Eleanor Stefani acquired the cottages and transformed them into a hotel, adding their own creative touches and artwork to create The Colony as it is known today. Managed by their son Jeffrey and his wife Mihae since 2019, The Colony offers a truly special summer retreat in the Northeast. The Colony of Wellfleet features 10 Bauhaus-style cottages overlooking Wellfleet harbor and bay, each designed for elegant functionality and furnished with pieces by leading modernists. Guests can enjoy reserved beach space, golf, tennis, pickleball, sailing lessons, and more at the club. The cafe offers coffee, pastries, lunch, and drinks with stunning views. Flexible membership options are available for guests.

Kinlin Grover Vacation Rentals is a premier real estate and travel agency located in Wellfleet, Massachusetts. With a prime location on U.S. 6, this institution offers a wide range of vacation rental properties for those looking to explore the charming town of Wellfleet and the surrounding areas. Whether you are seeking a beachfront cottage, a cozy cabin in the woods, or a luxurious waterfront villa, Kinlin Grover Vacation Rentals has the perfect accommodation for your getaway. Their team of experienced agents are dedicated to providing top-notch customer service and ensuring that your vacation experience is seamless and unforgettable. Contact Kinlin Grover Vacation Rentals today to start planning your dream vacation on Cape Cod.

Apple Tree Cape Cod Vacation Properties is a charming institution located at 40 Leilla Rich Drive in Wellfleet, Massachusetts, United States. As a park, real estate agency, and travel agency all rolled into one, we specialize in providing top-notch vacation properties for those looking to experience the beauty of Cape Cod. Our properties are nestled among the iconic apple trees of the region, offering a peaceful and serene setting for guests to relax and unwind. Whether you're looking for a cozy cottage for a romantic getaway or a spacious beachfront home for a family vacation, we have the perfect property for you. Let us help you create unforgettable memories on your next trip to Cape Cod.

Wellfleet by the Sea Cottages is a charming real estate and travel agency located at 370 Ocean View Drive in Wellfleet, Massachusetts. Our cottages offer a cozy and comfortable stay by the sea, perfect for those looking to escape the hustle and bustle of everyday life. With stunning ocean views and a peaceful atmosphere, our cottages provide the ideal setting for a relaxing vacation or a weekend getaway. Whether you're looking to rent a cottage for a week or purchase your own piece of paradise, Wellfleet by the Sea Cottages is here to help make your coastal dreams a reality.

Sunshine House Wellfleet is a charming lodging establishment located at 196 Chequessett Neck Road in Wellfleet, Massachusetts. Nestled in a tranquil and picturesque setting, this institution offers a comfortable and inviting atmosphere for guests looking to unwind and relax. With its convenient location near the coast, guests can enjoy easy access to the beach and other outdoor activities. The Sunshine House Wellfleet is the perfect place for a peaceful getaway in the heart of Cape Cod.

Starfish Vacation Village is a charming seaside retreat located at 2032 U.S. 6 in Wellfleet, Massachusetts. Nestled in the heart of Cape Cod, this idyllic resort offers guests a peaceful and relaxing getaway surrounded by natural beauty. The village features cozy cottages, a sparkling swimming pool, and lush gardens, creating the perfect setting for a memorable vacation. Whether you're looking to unwind on the beach, explore the nearby hiking trails, or simply enjoy a quiet evening by the fire pit, Starfish Vacation Village has something for everyone. Come experience the magic of Cape Cod at this hidden gem on the coast.

The Cottage on Great Pond in Wellfleet, Massachusetts offers a tranquil and picturesque retreat for those looking to escape the hustle and bustle of everyday life. Located at 111 Wiles Lane, this charming lodging option provides guests with a cozy and comfortable stay surrounded by the natural beauty of the area. Whether you're looking to relax by the pond, explore the nearby beaches, or simply unwind in a peaceful setting, the Cottage on Great Pond is the perfect destination for a rejuvenating getaway. With its convenient location and welcoming atmosphere, this institution is sure to provide a memorable and enjoyable experience for all who stay here.

The Furies Linen Rentals of Cape Cod is a home goods store located in Wellfleet, Massachusetts. We offer a wide range of high-quality linen rentals for your home or vacation rental on Cape Cod. From luxurious bedding to plush towels, we have everything you need to make your space feel cozy and inviting. Visit us at 2393 U.S. 6 to browse our selection and elevate your home decor with our stylish linens.

Pilgrim Spring House Rental is a real estate and travel agency located at 295 Pilgrim Spring Road in Wellfleet, Massachusetts, United States. This rental property offers a spacious and beautifully renovated house with stunning views of the Fox Island Conservation Area. The house features two levels of large deck space, perfect for enjoying the outdoors and dining al fresco. The property also includes a shaded picnic area, an outdoor shower, and parking for three vehicles. Inside, the house boasts a large and bright eat-in kitchen with modern appliances and plenty of counter space. The living room is spacious and comfortable, with flat-screen TVs and plenty of seating. There are also separate office areas for those who need to work while on vacation.

The Wellfleeter is a charming lodging located at 275 Kendrick Avenue in Wellfleet, Massachusetts. Nestled in the heart of this picturesque town, The Wellfleeter offers cozy accommodations and a warm, welcoming atmosphere for guests to enjoy. Whether you're looking for a peaceful retreat or a convenient home base for exploring the Cape Cod area, The Wellfleeter is the perfect choice. With comfortable rooms and attentive staff, this institution is sure to make your stay a memorable one.

Ocean View Cottages offers charming vacation cottages for rent in the picturesque town of Wellfleet, Massachusetts. Situated at 230 Pilgrim Road, our cottages provide guests with stunning views of the ocean and a serene escape from the hustle and bustle of everyday life. As a real estate and travel agency, we are dedicated to helping our guests find the perfect rental property for their vacation needs. Whether you're looking for a cozy retreat for a romantic getaway or a spacious cottage for a family vacation, Ocean View Cottages has something for everyone. Book your stay with us and experience the beauty of Wellfleet in comfort and style.

Wellfleet Vacation Home Rental offers a cozy and charming lodging option in the picturesque town of Wellfleet, Massachusetts. Located at 419 Nellie Road, our vacation home provides a comfortable and relaxing getaway for visitors looking to explore the beauty of Cape Cod. With spacious accommodations, modern amenities, and a convenient location near beaches, restaurants, and shops, our rental is the perfect choice for a memorable vacation experience. Whether you're looking for a peaceful retreat or an adventure-filled getaway, Wellfleet Vacation Home Rental has everything you need for a fantastic stay.

Cape Cod Catamaran Sailing Charters is a travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States. Offering morning and afternoon charters as well as sunset cruises from Wellfleet Harbor, this institution provides an authentic Cape Cod experience on their catamaran, Discovery. Escape the crowds and immerse yourself in the serene beauty of Cape Cod with a private daytime charter, where you can explore the bay, watch seals, or simply relax and enjoy the tranquility of the local waters. The experienced captain ensures a smooth and comfortable ride as you navigate Wellfleet Harbor and Cape Cod Bay.

Even'tide Resort & Cottages is a charming lodging establishment located in Wellfleet, Massachusetts. Situated at 650 U.S. 6, this resort offers cozy cottages and comfortable rooms for guests to enjoy a relaxing stay on Cape Cod. The resort is surrounded by beautiful scenery and is just a short drive away from the beach, making it the perfect destination for a seaside getaway. With friendly staff, clean accommodations, and a peaceful atmosphere, Even'tide Resort & Cottages is a great choice for those looking to unwind and rejuvenate in a tranquil setting.

Surf Side Cottages is a charming lodging option located at 370 Wilson Avenue in Wellfleet, Massachusetts, United States. This institution offers cozy and comfortable cottages for guests looking to enjoy a relaxing beach vacation. As a real estate agency, Surf Side Cottages also provides opportunities for those interested in purchasing a vacation home in this picturesque coastal town. Additionally, as a travel agency, they can assist guests in planning their ideal getaway to Wellfleet, whether it be for a weekend retreat or an extended stay. Experience the beauty of Cape Cod at Surf Side Cottages.

Chequessett Yacht & Country Club is a health institution located at 680 Chequessett Neck Road in Wellfleet, Massachusetts. This club offers a variety of activities including Golf, Tennis, Pickleball, and Sailing, all while overlooking the beautiful Wellfleet Harbor. The club features a nine-hole semi-links golf course, Novo Pro Turf tennis courts, and a Waterfront Beach Club. They also have venue spaces for waterfront weddings and special events, as well as a restaurant serving breakfast and lunch with a view of the 9th hole or Wellfleet Bay. Families can register their children for a summer program filled with various activities. Non-members can play the course for a fee, and riding carts are available for members during the winter months. Come enjoy the amenities and create lasting memories at Chequessett Yacht & Country Club in Cape Cod.

Cooks By The Ocean is a charming lodging institution located at 420 Lecount Hollow Road in Wellfleet, Massachusetts. Nestled along the picturesque coastline of Cape Cod, this cozy retreat offers guests a peaceful and relaxing escape by the ocean. With comfortable accommodations and a warm, welcoming atmosphere, Cooks By The Ocean is the perfect destination for those looking to unwind and enjoy the beauty of the seaside. Whether you're seeking a romantic getaway or a family vacation, this charming inn is sure to make your stay unforgettable.

Brownies Cabins is a charming lodging institution nestled in the picturesque town of Wellfleet, Massachusetts. Offering cozy and comfortable cabins for guests to relax and unwind, Brownies Cabins provides a peaceful retreat surrounded by nature. The cabins are equipped with modern amenities to ensure a comfortable stay, and the friendly staff are always on hand to assist with any requests. Whether you're looking for a romantic getaway or a family vacation, Brownies Cabins is the perfect choice for a memorable stay in Wellfleet.

The White House on Chipman Cove is a prestigious real estate and travel agency located at 105 Old Pier Road in Wellfleet, Massachusetts. Situated in a picturesque coastal town, this institution offers luxurious vacation rentals and stunning waterfront properties for sale. With a team of experienced agents and travel experts, The White House on Chipman Cove provides unparalleled service and expertise to clients looking to invest in or rent a piece of paradise in this beautiful seaside community. Whether you're searching for a dream vacation home or planning a relaxing getaway, this institution is your go-to destination for all things real estate and travel in Wellfleet.

Green Haven Cottage Condominiums is a charming lodging institution located at 633 U.S. 6 in Wellfleet, Massachusetts. Nestled in a serene and picturesque setting, these cozy cottages offer a peaceful retreat for guests looking to unwind and relax. Each cottage is beautifully decorated and fully equipped with modern amenities to ensure a comfortable stay. The property also features lush gardens, a communal outdoor seating area, and easy access to nearby attractions such as beaches, hiking trails, and local shops and restaurants. Whether you're seeking a romantic getaway or a family vacation, Green Haven Cottage Condominiums provides the perfect home away from home in the heart of Cape Cod.

Main House is a reputable real estate and travel agency located at 575 Chequessett Neck Road in Wellfleet, Massachusetts. Our team of experienced professionals is dedicated to helping clients find their dream homes or plan the perfect getaway. Whether you're looking to buy or rent a property, or book a vacation, Main House is here to provide top-notch service and expertise. Visit us today and let us help you make your real estate or travel dreams a reality.

Kinlin Grover Real Estate is a leading real estate agency located in Wellfleet, Massachusetts. With a prime location on U.S. 6, this reputable institution offers a wide range of services to help clients buy, sell, or rent properties in the area. Their team of experienced agents is dedicated to providing top-notch customer service and expert guidance throughout the real estate process. Whether you are looking for a beachfront vacation home or a cozy cottage in the countryside, Kinlin Grover Real Estate has the expertise to help you find your dream property. Contact them today to learn more about their listings and services.

The Apartments at Duck Creek offer comfortable and cozy lodging in the charming town of Wellfleet, Massachusetts. Located at 135 Commercial Street, this institution provides a peaceful retreat for visitors looking to relax and unwind. The apartments are well-appointed and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy easy access to the nearby beaches, shops, and restaurants, making it an ideal choice for those looking to explore the beauty of Cape Cod. Whether you're planning a romantic getaway or a family vacation, the Apartments at Duck Creek provide a welcoming and convenient accommodation option.

Christie's International Real Estate Atlantic Brokerage is a prestigious real estate agency located at 7 Bayberry Court in Nantucket, Massachusetts. As the exclusive affiliate for Provincetown, Truro, Wellfleet, Eastham, Orleans, Brewster, Chatham, Harwich, and Nantucket, Atlantic Brokerage offers unparalleled expertise and local knowledge to help clients find their dream properties and build long-term wealth. With personalized solutions and a commitment to excellence, Atlantic Brokerage is dedicated to exceeding client expectations. Independently owned and operated, Atlantic Brokerage is a trusted partner in the luxury real estate market. Visit their office at 584 Route 28 in Harwich Port, MA 02646 to discover the difference of working with Christie's International Real Estate Atlantic Brokerage.

Nestled in the charming town of Wellfleet, Massachusetts, the Weidlinger House offers a serene and welcoming retreat for travelers seeking a cozy place to stay. Located at 54 Valley Road, this quaint lodging institution provides a peaceful atmosphere and comfortable accommodations for guests to relax and unwind. Whether you're visiting for a weekend getaway or an extended vacation, the Weidlinger House is the perfect home away from home. Enjoy the beauty of Wellfleet and all that it has to offer, while staying in this charming and inviting establishment.