TOP 10 Vacation house rentals in Chatham, Massachusetts

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Eider Duck Cottages is a charming lodging institution located at 1470 Main Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a tranquil setting, these cozy cottages offer a perfect retreat for those seeking a peaceful and relaxing getaway. Each cottage is beautifully decorated and equipped with all the modern amenities to ensure a comfortable stay. Guests can enjoy the serene surroundings, explore the nearby attractions, or simply unwind on the porch and take in the breathtaking views. Eider Duck Cottages is the ideal destination for a memorable vacation on Cape Cod.

Pine Shore Cottages is a charming lodging destination located at 1370 Main Street in the picturesque town of Chatham, Massachusetts. Nestled among the pine trees, this cozy retreat offers a peaceful and relaxing atmosphere for guests to enjoy. As both a lodging and real estate agency, Pine Shore Cottages provides comfortable accommodations for travelers looking to experience the beauty of Cape Cod, as well as opportunities for those interested in purchasing a vacation home in this desirable location. With a dedicated team of professionals, Pine Shore Cottages also doubles as a travel agency, helping guests plan their perfect getaway to this idyllic seaside town. Experience the tranquility and beauty of Chatham at Pine Shore Cottages.

Chatham Rentals is a reputable real estate and travel agency located at 1173 Main Street in Chatham, Massachusetts, United States. Specializing in vacation rentals, property management, and travel accommodations, Chatham Rentals offers a wide range of options for those looking to explore the beautiful Cape Cod area. With a dedicated team of professionals, exceptional customer service, and a diverse portfolio of properties, Chatham Rentals is the perfect choice for your next vacation or real estate investment. Contact us today to learn more about our services and start planning your next adventure in Chatham!

Chatham Vacation Rentals is a reputable real estate agency located at 1291 Main Street in the picturesque town of Chatham, Massachusetts. Specializing in vacation rentals, they offer a wide range of beautiful properties for visitors looking to experience the charm and beauty of Cape Cod. Whether you're seeking a cozy cottage by the beach or a spacious waterfront estate, Chatham Vacation Rentals has the perfect accommodation for your next getaway. Their friendly and knowledgeable staff are dedicated to helping you find the ideal rental property to make your vacation unforgettable. With their prime location in Chatham, you'll have easy access to the town's shops, restaurants, and beaches, ensuring a truly memorable vacation experience.

Chatham Harborview Lodge is a stunning vacation rental located at 200 Barcliff Avenue in Chatham, Massachusetts. This beautiful property offers breathtaking views of Oyster Pond and provides access to the water for activities such as kayaking and paddleboarding. Perfect for family reunions, the lodge offers both togetherness and privacy, along with versatile and comfortable sleeping arrangements. The open-floor-plan house features a sophisticated beach-style decor, spacious grounds, and refreshing ocean breezes. Guests can relax on the 30-foot deck overlooking the picturesque harbor, or take a short walk to the nearby marina or Harding's Beach. With two kitchens, multiple bedrooms, and plenty of space to spread out, this property is ideal for large groups and extended families. The owner, Kibibi, is responsive and accommodating, ensuring a memorable stay for all guests. Don't miss out on the opportunity to experience "Summer Glamping" at Chatham Harborview Lodge. Book now for an unforgettable Cape Cod vacation!

Pleasant Forest Shores cottages is a charming lodging establishment located at 259 Pleasant Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a tranquil forest setting, the cottages offer a peaceful retreat for guests looking to escape the hustle and bustle of everyday life. Each cottage is tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the serene surroundings, take a leisurely stroll to the nearby beach, or explore the quaint shops and restaurants in the town center. Whether you are seeking a romantic getaway or a family vacation, Pleasant Forest Shores cottages provide the perfect setting for a relaxing and rejuvenating experience.

Chatham Seaside Cottages is a charming lodging institution located at 439 Ridgevale Road in the picturesque town of Chatham, Massachusetts. Nestled along the stunning coastline of Cape Cod, this quaint retreat offers guests a peaceful and relaxing getaway by the sea. The cozy cottages provide a comfortable and cozy atmosphere, perfect for a romantic weekend escape or a family vacation. With easy access to the beach and nearby attractions, Chatham Seaside Cottages is the ideal destination for those looking to experience the beauty of the Massachusetts coast.

Metter's Cottages is a charming accommodation located at 84 Chatharbor Lane in the picturesque town of Chatham, Massachusetts. Nestled in a tranquil setting, these cozy cottages offer a perfect retreat for those looking to escape the hustle and bustle of everyday life. Each cottage is beautifully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the peaceful surroundings, relax on the private deck, or take a short stroll to the nearby beach. Metter's Cottages is the ideal choice for a relaxing getaway on Cape Cod.

Chatham Beach Cottages is a charming waterfront retreat located on Little Beach Road in the picturesque town of Chatham, Massachusetts. Nestled along the sandy shores of the Atlantic Ocean, this cozy getaway offers a collection of well-appointed cottages with stunning ocean views and easy access to the beach. Guests can relax on their private deck, take a leisurely stroll along the shoreline, or explore the quaint shops and restaurants in town. Whether seeking a romantic escape or a family vacation, Chatham Beach Cottages provides a peaceful and idyllic setting for a memorable coastal retreat.

Chatham Vacation Properties is a reputable real estate agency located at 1429 Massachusetts Avenue in Lexington, Massachusetts. Specializing in vacation properties, they offer a wide range of rental and sales options for those looking to experience the beauty of Cape Cod. With a team of experienced agents, Chatham Vacation Properties is dedicated to providing top-notch service and helping clients find their perfect vacation home. Whether you're looking for a quaint cottage by the beach or a luxurious waterfront estate, Chatham Vacation Properties has something for everyone. Visit their office today to start planning your dream vacation in Cape Cod.

Chatham Concierge is a one-stop destination for all your Cape Cod vacation needs. Located at 20 Heritage Lane in Chatham, Massachusetts, this institution offers high-quality linen rentals and professional photography services to enhance your stay on the beautiful Cape Cod peninsula. Whether you're looking to upgrade your vacation home with luxurious linens or capture unforgettable memories with stunning photographs, Chatham Concierge has you covered. Experience the ultimate convenience and luxury with Chatham Concierge - your go-to home goods store, real estate agency, and store all in one.

The Captain Freeman Inn, located at 15 Breakwater Road in Brewster, Massachusetts, is a beautifully restored Sea Captain's mansion just a short walk away from Breakwater Beach. This award-winning Bed and Breakfast has been recognized with the Tripadvisor Certificate of Excellence for the past 11 years, offering guests a deluxe seaside experience year-round. Guests can enjoy the outdoor heated salt water swimming pool and custom firepit, providing the ultimate in luxury and relaxation in every season. The inn also offers a gourmet three-course breakfast made with farm-to-table ingredients, served in a charming indoor dining area or on the screened porch.

Pilgrim Village is a charming lodging institution located at 1370 Main Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a serene and peaceful setting, Pilgrim Village offers comfortable accommodations and a warm and welcoming atmosphere for guests looking to unwind and relax. With its convenient location near the town center and attractions such as beaches, shops, and restaurants, Pilgrim Village is the perfect choice for a memorable stay on Cape Cod. Whether you are visiting for a weekend getaway or an extended vacation, Pilgrim Village promises a delightful and memorable experience for all guests.

Eelman's Point House is a reputable real estate agency located at 47 Horseshoe Lane South in Chatham, Massachusetts, United States. With a team of experienced professionals, they offer top-notch services for buying, selling, and renting properties in the area. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront estate, Eelman's Point House can help you find the perfect property to suit your needs. Their dedication to client satisfaction and attention to detail make them a trusted choice for all your real estate needs in Chatham.

Lower Cape Escape is a premier real estate and travel agency located in Chatham, Massachusetts. Situated at 247 Morton Road, this institution specializes in providing luxurious vacation rentals and properties for sale in the Lower Cape Cod area. Whether you are looking for a cozy beachfront cottage or a spacious family home, Lower Cape Escape offers a wide range of options to suit every taste and budget. With their expert knowledge of the local real estate market and dedication to customer satisfaction, Lower Cape Escape is your go-to destination for all your vacation rental and property buying needs in Cape Cod.

New England Vacation Rentals and Property Management is a premier institution located at 1455 Main Street in Chatham, Massachusetts. This multi-faceted establishment offers a range of services including lodging, real estate agency, and travel agency assistance. Whether you're looking for a cozy vacation rental for a weekend getaway or seeking professional property management services, this institution has you covered. With a prime location in the heart of New England, they specialize in providing top-notch accommodations and expert guidance for all your vacation and real estate needs. Visit New England Vacation Rentals and Property Management for a seamless and memorable experience in beautiful Chatham, Massachusetts.

Pine Acres Realty - Rental Division is a reputable real estate agency and travel agency located at 20 Heritage Lane in Chatham, Massachusetts, United States. Specializing in vacation rentals, they offer a wide range of properties in the beautiful Cape Cod area. With a team of experienced agents dedicated to providing exceptional customer service, Pine Acres Realty - Rental Division is the perfect choice for anyone looking to find their dream vacation rental in this picturesque coastal town. Whether you're looking for a beachfront cottage or a cozy cabin in the woods, they have the perfect property to suit your needs. Contact them today to start planning your next getaway!

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.

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.

Kinlin Grover Vacation Rentals is a renowned real estate and travel agency located at 856 Main Street in the picturesque town of Chatham, Massachusetts. Offering a wide range of vacation rental properties for visitors looking to explore the charming Cape Cod region, Kinlin Grover Vacation Rentals is committed to providing exceptional service and top-notch accommodations. Whether you're looking for a cozy cottage by the beach or a luxurious waterfront estate, their team of experienced agents is dedicated to helping you find the perfect vacation rental for your needs. With a reputation for excellence and a passion for hospitality, Kinlin Grover Vacation Rentals is your go-to destination for a memorable Cape Cod getaway.

Whydah Figawi is a unique institution located at 138 Whidah Road in Chatham, Massachusetts, United States. This establishment serves as both a real estate agency and a travel agency, offering a range of services to help clients find their dream vacation home or plan their next adventure. With a team of experienced professionals and a commitment to exceptional customer service, Whydah Figawi is a trusted resource for those looking to buy or rent properties in the beautiful coastal town of Chatham, as well as for travelers seeking personalized and memorable travel experiences. Visit Whydah Figawi today and let them help you turn your real estate and travel dreams into reality.

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.

John C Ricotta & Associates is a reputable real estate agency located at 1181 Main Street in Chatham, Massachusetts, United States. With years of experience in the industry, they specialize in helping clients buy and sell residential properties in the picturesque town of Chatham. Their team of dedicated professionals provides personalized service and expert guidance throughout the entire real estate transaction process. Whether you are looking for your dream home or hoping to sell your current property, John C Ricotta & Associates is committed to helping you achieve your real estate goals. Contact them today to learn more about their services and how they can assist you in your real estate journey.

Yarmouth Cape Cod is a reputable institution located at 279 Orleans Road in Chatham, Massachusetts, United States. As a real estate agency, they specialize in helping clients find their dream homes or vacation rentals in the beautiful Cape Cod area. Additionally, they also operate as a travel agency, offering personalized vacation planning services for those looking to explore the charming town of Yarmouth and beyond. With their expert knowledge of the local area and dedication to customer satisfaction, Yarmouth Cape Cod is the perfect choice for all your real estate and travel needs in Cape Cod.

Welcome to Suzanne Crerar at Stone House Properties, your premier real estate partner located at 38 Main Street, West Stockbridge, Massachusetts. Serving the beautiful regions of Berkshire County, Massachusetts, and Columbia County, New York's Upper Hudson Valley, we are a well-established brokerage firm dedicated to providing exceptional services for both buyers and sellers. Our region is renowned for its breathtaking natural beauty, with the Berkshires and Upper Hudson Valley offering picturesque landscapes of rolling hills and expansive valleys. In addition to the stunning scenery, our area is rich in cultural landmarks, including Tanglewood, MASS MoCA, and the Olana State Historic Site, making it a truly desirable location for your next home.

Welcome to Jennifer Capala, William Pitt Sotheby's International Realty in Lenox, Massachusetts! Located at 34 Church Street, our office is your gateway to exceptional real estate services in the Berkshires and beyond. With over 15 years of experience, Jennifer Capala stands out for her unwavering commitment to superior professional standards and her creative approach to overcoming challenges. Her clients describe her as enthusiastic, knowledgeable, responsive, ethical, and extremely helpful. Jennifer's passion for real estate ignited over 20 years ago when she transformed a Brooklyn firehouse into a livable, multi-use space, earning features in New York Magazine and The NY Times. Her background as a commercial photographer in New York City, documenting architecture and interiors, has honed her ability to assess the true potential of any property with a keen eye for design and construction.

Welcome to Keytoria Jenkins, REALTOR® Located in the heart of Pittsfield, Massachusetts, at 137 North Street, Keytoria Jenkins, REALTOR® is dedicated to providing exceptional real estate services with integrity and a personal touch. Born and raised in Greenville, SC, Keytoria brings a unique blend of Southern hospitality, community connections, and a commitment to service that ensures her clients receive the best experience possible.

Welcome to Whiteacre Properties LLC, your trusted real estate partner located at 150 East Central Street, Natick, Massachusetts 01760. We specialize in offering a fast, simple, and stress-free way to sell your house for cash in Boston and the surrounding areas. Whether you're facing foreclosure, dealing with an inherited property, or simply need to sell quickly due to life changes, we are here to help. At Whiteacre Properties, we understand the challenges of selling a home. That's why we offer a straightforward cash-buying program that eliminates the need for real estate agents, open houses, and costly repairs. Our process is designed to be as hassle-free as possible, allowing you to sell your house in any condition, without the burden of maintenance, cleaning, or agent fees.

Welcome to Steps to Solutions, Inc., your trusted real estate agency located in the heart of Lynn, Massachusetts. Situated at 391 Chatham Street, we are dedicated to serving the vibrant community of Lynn and the surrounding areas with exceptional real estate services. Our team of experienced professionals is committed to guiding you through every step of the buying, selling, or renting process, ensuring a seamless and rewarding experience. At Steps to Solutions, Inc., we understand that real estate transactions can be complex and emotional. That's why we focus on delivering personalized solutions tailored to your unique needs and goals. Whether you're a first-time homebuyer, looking to upgrade, or seeking investment opportunities, we provide expert advice and insights to help you make informed decisions.

Welcome to EXIT Realty Beatrice Associates, your trusted real estate partner located in the heart of Lynn, Massachusetts. Situated at 49 Chatham Street, our agency is dedicated to providing exceptional service and expert guidance to clients in the vibrant and diverse communities of the North Shore. As a premier real estate agency, we specialize in buying, selling, and investing in residential and commercial properties. Our team of experienced and knowledgeable agents is committed to helping you navigate the real estate market with ease and confidence. Whether you're a first-time homebuyer, an experienced investor, or looking to sell your property, EXIT Realty Beatrice Associates is here to ensure a seamless and rewarding experience. Discover the difference that personalized service and local expertise can make. Contact us today to start your real estate journey!