TOP 10 Best Vacation planning in Chatham, Massachusetts

North Chatham Outfitters is a store located at 300 Orleans Road in Chatham, Massachusetts. This institution is dedicated to providing outdoor enthusiasts with the gear and knowledge they need to enjoy the beautiful beaches and waters of Cape Cod. Whether you are into freshwater fishing, inshore fishing, offshore fishing, hunting, or a scenic kayak or paddleboard tour, NCO has everything you need for a special and productive day outdoors. Our knowledgeable staff is always available to answer your questions and help you find the right gear for your outdoor adventures. Please note that charters are booked through the charter companies, not through our shop. Stop by North Chatham Outfitters for an extensive selection, great prices, and top-notch service from our NCO family.

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!

William Raveis Real Estate in Chatham, Massachusetts is a trusted institution offering a wide range of services including finance, insurance, real estate, and travel assistance. Located at 37 Cross Street, this establishment is known for its professional and experienced staff who are dedicated to helping clients achieve their financial and real estate goals. Whether you are looking to buy or sell a property, secure insurance coverage, or plan your next vacation, William Raveis Real Estate is the go-to destination for all your needs. Visit us today and experience the exceptional service and expertise that sets us apart from the rest.

Adventure Chatham is a premier travel agency located at 1150 Queen Anne Road in Harwich, Massachusetts. Specializing in unique and unforgettable travel experiences, Adventure Chatham offers a wide range of adventure tours and packages for those seeking excitement and exploration. From thrilling outdoor activities to cultural immersion experiences, our team of expert travel agents will help you plan the adventure of a lifetime. Discover the beauty of Chatham and beyond with Adventure Chatham.

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!

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.

The Platinum Pebble Boutique Inn is a luxurious adults-only lodging located at 186 Belmont Road in Harwich, Massachusetts, United States. This upscale Cape Cod accommodation offers premium amenities such as gourmet breakfast, complimentary bicycles, beach chairs, pool towels, and a relaxing beach vibe. Each room is tastefully decorated with modern furnishings and luxurious linens, providing a blend of comfort and coastal elegance. Guests can enjoy a peaceful night's sleep on Verlo mattresses and Comphy bedsheets, and start their day with a delicious breakfast before exploring the nearby towns of Falmouth, Chatham, and Provincetown. The inn's central location makes it the ideal base for a Cape Cod vacation, with easy access to Martha's Vineyard and Nantucket.

By The Sea Guests is a charming lodging institution located at 57 Chase Avenue in Dennis, Massachusetts, United States. Nestled on the beach, our guest rooms offer one or two beds, private bathrooms, TVs, and mini fridges, with most rooms boasting oceanfront or partial ocean views. With 12 guest rooms in the inn, guests can enjoy a comfortable stay with breakfast included seasonally from May through October. For those seeking more space and amenities, our Suites feature open-concept layouts with full kitchens, living rooms, private bathrooms, and private decks or balconies with side partial ocean views. We offer three one-bedroom suites and two two-bedroom suites, perfect for families or larger groups. Breakfast is not included but can be purchased during peak season.

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.

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.

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!

Friends of Monomoy is a renowned travel agency located at 30 Wikis Way in Chatham, Massachusetts. Our dedicated team of experts specializes in creating unforgettable travel experiences to the beautiful Monomoy Island and surrounding areas. Whether you're looking for a relaxing beach getaway or an adventurous outdoor expedition, we can tailor a unique itinerary to suit your preferences. With our insider knowledge and personalized service, we strive to ensure that every trip with Friends of Monomoy is truly exceptional. Visit us today and let us help you plan your next unforgettable vacation.

Son of a Sailor, LLC. is a travel agency located at 80 Bridge Street in the charming town of Chatham, Massachusetts. Specializing in creating unforgettable travel experiences, Son of a Sailor offers personalized services to help clients plan their dream vacations. Whether you're looking to explore the historic sights of New England or relax on the beautiful beaches of Cape Cod, the team at Son of a Sailor is dedicated to making your travel dreams a reality. Visit us today and let us help you plan your next adventure!

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.