TOP 30 Best Vacation cottage rentals in Wellfleet, Massachusetts

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.

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.

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.

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.

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.

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.

Cassick Valley Cottage is a charming lodging institution located at 75 Cassick Valley Road in Wellfleet, Massachusetts, United States. Nestled in the picturesque Cassick Valley, this cozy cottage offers a peaceful retreat for travelers looking to escape the hustle and bustle of city life. Surrounded by lush greenery and beautiful scenery, guests can relax and unwind in a serene environment. The cottage is equipped with comfortable accommodations and modern amenities to ensure a comfortable stay for all guests. Whether you're looking for a romantic getaway or a family vacation, Cassick Valley Cottage is the perfect destination for a relaxing and rejuvenating experience.

Bountiful Cottage is a charming institution located at 185 Pleasant Point Avenue in Wellfleet, Massachusetts. Nestled in a picturesque setting, this cozy cottage offers a tranquil and inviting atmosphere for visitors to relax and unwind. With its warm and welcoming ambiance, Bountiful Cottage provides a comfortable and peaceful retreat for guests looking to escape the hustle and bustle of everyday life. Whether you are seeking a romantic getaway or a quiet weekend retreat, Bountiful Cottage is the perfect destination for those looking to experience the beauty and charm of Wellfleet, Massachusetts.

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.

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.

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.

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.

Located in Wellfleet, Massachusetts, Maurice’s Campground offers a unique camping experience surrounded by beautiful pine woods and the refreshing ocean breeze. Whether you choose to stay in a cozy cottage, pitch a tent, or bring your trailer, Maurice’s Campground provides the perfect Cape Cod nature experience. Situated next to the National Seashore, guests can easily access crystal clear ponds, world-renowned beaches, and the Cape Cod Trail for biking adventures. Nature enthusiasts will appreciate the proximity to the Wellfleet Audubon for birdwatching and nature walks. For a bit of nostalgia, guests can enjoy a classic drive-in movie just across the street. With 2024 reservations now available, book your stay at Maurice’s Campground and create unforgettable memories with your family.

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.

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.

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.

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.

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.