TOP 10 Vacation cottage rentals in Wellfleet, Massachusetts

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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.

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.

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.

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.

Wellfleet Bayside Cottage is a charming lodging located at 65 Pier Road in the picturesque town of Wellfleet, Massachusetts. Nestled along the beautiful shores of the bay, this cozy cottage offers a peaceful retreat for guests looking to relax and unwind. The cottage features comfortable accommodations, a fully equipped kitchen, and a private deck with stunning views of the water. Whether you're looking for a romantic getaway or a family vacation, Wellfleet Bayside Cottage is the perfect destination for a memorable stay on the Cape.

Beach Rose Cottages is a charming lodging institution located at 164 Kendrick Avenue in Wellfleet, Massachusetts, United States. Nestled in a picturesque coastal town, Beach Rose Cottages offers cozy and comfortable accommodations for guests looking to escape and unwind by the beach. The cottages are beautifully decorated and equipped with modern amenities to ensure a relaxing stay. With its convenient location near the beach, guests can enjoy stunning ocean views, tranquil walks along the shore, and a variety of outdoor activities. Whether you're seeking a romantic getaway or a family vacation, Beach Rose Cottages provides a peaceful retreat for all.

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.

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.

Black Fish Cottage is a charming and cozy real estate and travel agency located at 85 Baker Road in Wellfleet, Massachusetts. Our team specializes in helping clients find their dream vacation rental or summer home in this picturesque coastal town. With a personalized approach and attention to detail, we strive to make the process of buying or renting a property as seamless and enjoyable as possible. Whether you're looking for a weekend getaway or a long-term investment, Black Fish Cottage is here to help you every step of the way. Visit us today and let us help you find the perfect place to call home in Wellfleet.

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.

Cozy Cottage is a charming and inviting institution located at 215 Pilgrim Spring Road in Wellfleet, Massachusetts. Nestled in a picturesque setting, this quaint cottage offers a warm and welcoming atmosphere for guests to relax and unwind. Whether you are looking for a peaceful retreat or a romantic getaway, Cozy Cottage provides a cozy and comfortable escape from the hustle and bustle of everyday life. With its convenient location in Wellfleet, guests can easily explore the natural beauty and attractions of Cape Cod while enjoying the comforts of home. Experience the charm and hospitality of Cozy Cottage during your stay in this idyllic New England setting.

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.

Highland House is a real estate and travel agency located at 45 Highland Avenue in Wellfleet, Massachusetts, United States. The institution is within walking distance to Pleasant Point Landing, where guests can enjoy swimming and kayaking at high tide and beach walks at low tide. Pleasant Point is a charming bayside neighborhood in South Wellfleet. The rental rates for Highland House are $2200 per week and $8000 per month, with a minimum stay of one week. There is also a $170 cleaning fee and 14.45% tax added to the total cost. The house is conveniently located near the Cape Cod Bike Trail and Le Count Hollow Ocean Beach, making it easy for guests to explore the area.

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.

Duarte Downey Real Estate is a well-established and highly respected real estate agency located in Truro, Massachusetts. As the oldest and most recognized agency in Cape Cod, we specialize in Truro MA Rentals, North Truro MA Rentals, South Truro MA Rentals, Provincetown MA Rentals, Wellfleet MA Rentals, South Wellfleet MA Rentals, and Eastham MA Rentals. Whether you are a renter searching for the perfect vacation home, a buyer looking for your dream property, or a seller seeking top-notch agents to sell your house quickly and for the best price, we have the expertise and tools to meet your needs. Stay up to date with new listings, read informative real estate articles on our blog, and easily calculate your monthly payments with current mortgage rates. Trust Duarte Downey Real Estate to make your real estate experience seamless and successful.

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.

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.

VIP Real Estate, Inc. is a premier real estate agency located at 10 Pine Point Road in Wellfleet, Massachusetts, United States. Our team of experienced and dedicated agents are committed to providing top-notch service to our clients in buying, selling, and renting properties in the area. With a strong focus on customer satisfaction and attention to detail, VIP Real Estate, Inc. strives to make the real estate process as smooth and stress-free as possible. Whether you are looking for a vacation home, investment property, or your dream house, trust VIP Real Estate, Inc. to help you find the perfect property to suit your needs. Contact us today to start your real estate journey with VIP Real Estate, Inc.

Cape Cod Oceanview Realty is a premier real estate agency located in Wellfleet, Massachusetts. Our experienced agents specialize in helping clients buy and sell properties in the beautiful Outer Cape region. With a strong focus on providing exceptional customer service and market expertise, we are dedicated to helping our clients find their dream coastal home. Whether you are looking for a vacation getaway or a permanent residence, our team is here to assist you every step of the way. Visit us at 1580 State Highway Route 6 to learn more about the incredible opportunities that await you in this stunning seaside community.

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.

Hidden Hollow is a unique and tranquil institution nestled at 90 Lecount Hollow Road in Wellfleet, Massachusetts. Surrounded by the natural beauty of the area, Hidden Hollow offers a peaceful retreat for individuals seeking relaxation and rejuvenation. With a focus on wellness and mindfulness, guests can enjoy a variety of holistic treatments and activities designed to promote a sense of inner peace and harmony. Whether you are looking to escape the hustle and bustle of everyday life or simply unwind in a serene environment, Hidden Hollow provides the perfect setting for a truly restorative experience.

Hatch House is a charming and historic institution located at 309 Bound Brook Way in Wellfleet, Massachusetts, United States. This beautiful property offers a serene and peaceful environment for individuals seeking a retreat from the hustle and bustle of everyday life. Nestled in a picturesque setting, Hatch House provides a unique opportunity for guests to relax and rejuvenate in a tranquil atmosphere. With its welcoming ambiance and cozy accommodations, this institution is the perfect destination for those looking to unwind and reconnect with nature. Whether you are seeking a quiet getaway or a place to host a special event, Hatch House is the ideal choice for your next escape.

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.

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.