TOP 10 Massachusetts vacation resorts in Chatham, Massachusetts

Located in the picturesque town of Harwich, Massachusetts, the Winstead Inn And Beach Resort offers a truly unique Cape Cod vacation experience. With two properties to choose from, guests can enjoy the charm of the inn in Harwich Center or the beachfront resort in Harwich Port. The Winstead Inn features elegant rooms individually decorated for a luxurious stay, with amenities such as a swimming pool, beautiful grounds, and a spacious great room. Guests can also take advantage of the private beach at the Beach Resort, just a short shuttle ride away.

Chatham Tides is a charming lodging establishment located at 394 Pleasant Street in the picturesque town of Chatham, Massachusetts. Situated in the United States, this quaint inn offers a cozy and relaxing atmosphere for guests looking to unwind and enjoy the beauty of Cape Cod. With its convenient location near the beach and various local attractions, Chatham Tides is the perfect destination for a peaceful getaway. Enjoy comfortable accommodations, friendly service, and a memorable stay at this lovely institution.

Pleasant Bay Village Resort is a charming lodging institution located at 1191 Orleans Road in the picturesque town of Chatham, Massachusetts, United States. Situated near the stunning Pleasant Bay, this resort offers guests a peaceful and serene retreat surrounded by natural beauty. The resort features comfortable accommodations, including cozy cottages and well-appointed guest rooms, perfect for a relaxing getaway. Guests can enjoy amenities such as a swimming pool, tennis courts, and a delicious on-site restaurant. Whether you're looking for a romantic escape or a family vacation, Pleasant Bay Village Resort provides a tranquil and idyllic setting for your stay in Cape Cod.

Chatham Bars Inn is a luxurious five-star oceanfront lodging located at 297 Shore Road in Chatham, Massachusetts, United States. With stunning views of the ocean and a rich history dating back to 1914, this iconic institution offers guests a truly unforgettable experience. Recently recognized as the #1 resort in Massachusetts and #8 in the world by Condé Nast Traveler's Readers' Choice Awards, Chatham Bars Inn is known for its warm hospitality and world-class amenities. Guests can relax and rejuvenate at the Forbes Four-Star awarded Spa at Chatham Bars Inn, where they can enjoy a variety of treatments designed to soothe the body, mind, and soul. The culinary team at Chatham Bars Inn is also top-notch, with new menus at the signature restaurant, STARS, and the beloved Sacred Cod Tavern.

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!

Del Mar Vacations - Chatham Rentals is a reputable real estate and travel agency located at 30 Captain Richards Way in Chatham, Massachusetts. Specializing in vacation rentals in the charming town of Chatham, this institution offers a wide range of properties for visitors looking to explore Cape Cod. Whether you're searching for a cozy beachfront cottage or a luxurious waterfront estate, Del Mar Vacations - Chatham Rentals has the perfect accommodation for your getaway. With exceptional customer service and a commitment to providing top-notch accommodations, this agency ensures that your vacation experience is nothing short of unforgettable. Book your next Cape Cod vacation with Del Mar Vacations - Chatham Rentals and create lasting memories in this beautiful coastal destination.

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.

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.

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.

Kingfisher Harwich Port is a newly renovated lodging institution located at 1 Braddock Street in Harwich, Massachusetts, United States. Situated just steps away from Bank Street Beach and a short walk from the shops and restaurants in Harwich Port, our hotel offers guests a relaxing Cape Cod vacation experience. Our clean, updated rooms feature modern amenities such as free WiFi, individual A/C, flat screen TV with DirecTV channels, microwave, Keurig coffee maker, and mini-fridge. During your stay, you can enjoy the convenience of receiving a welcome text by 4pm on the day of your arrival, allowing you to access your room without the need to stop at the office. Complimentary onsite parking is available with a parking pass provided in your room. Housekeeping is provided by request only, ensuring that you can relax without interruptions.

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.

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.

The Priscilla House is a charming lodging establishment located at 388 Main Street in the picturesque town of Chatham, Massachusetts. This historic house offers a cozy and welcoming atmosphere for guests to relax and unwind during their stay on Cape Cod. With comfortable accommodations and a convenient location near local attractions and amenities, The Priscilla House is the perfect choice for a memorable getaway in the United States.

The True North House is a charming lodging institution located at 86 Highland Avenue in the picturesque town of Chatham, Massachusetts. Situated in the heart of the United States' Cape Cod region, this cozy retreat offers guests a peaceful and relaxing atmosphere to unwind and recharge. With comfortable accommodations and personalized service, The True North House is the perfect destination for those seeking a tranquil getaway by the sea. Immerse yourself in the beauty of Cape Cod and experience true hospitality at The True North House.

BlueWater Entertainment Group LLC is a premier travel agency located in Chatham, Massachusetts. Offering unique and unforgettable experiences on Cape Cod, this agency specializes in water-based adventures. From shark sightings to whale watching, private ferry rides to Nantucket, and deep-sea fishing excursions, BlueWater Entertainment Group LLC provides a range of exciting activities for all ages. Additionally, they offer relaxing beach days complete with fresh seafood cookouts on remote Cape Cod beaches. With a focus on creating memorable experiences, this travel agency is the perfect choice for those looking to explore the beauty of Cape Cod from a different perspective.

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!

Monomoy Island Ferry is a renowned institution located at 80 Bridge Street in Chatham, Massachusetts, United States. Offering scenic and convenient transportation services to Monomoy Island, this ferry company provides visitors with a unique opportunity to explore the natural beauty and wildlife of the area. With knowledgeable guides and comfortable vessels, Monomoy Island Ferry ensures a memorable and educational experience for all passengers. Whether you're looking to spot seals, birds, or simply enjoy the stunning views of the Cape Cod coastline, a trip with Monomoy Island Ferry is a must-do activity for nature lovers and adventure seekers alike.

Lilly Pulitzer is a vibrant and colorful clothing store located at 483 Main Street in Chatham, Massachusetts. Known for their iconic prints and resort wear, Lilly Pulitzer offers a wide range of clothing and accessories for women, men, and children. Step into this charming store and immerse yourself in the world of Lilly Pulitzer, where every piece is designed to bring a touch of sunshine and happiness to your wardrobe. Whether you're looking for a statement dress for a special occasion or a casual yet stylish outfit for everyday wear, Lilly Pulitzer has something for everyone. Visit the store and experience the timeless elegance and playful sophistication that defines the Lilly Pulitzer brand.

Oyster Pond Beach is a picturesque tourist attraction located at 80 Stage Harbor Road in Chatham, Massachusetts, United States. This stunning beach offers visitors a serene and relaxing escape with its crystal-clear waters, soft sandy shores, and breathtaking views of the surrounding natural beauty. Whether you're looking to sunbathe, swim, or simply unwind by the water, Oyster Pond Beach is the perfect destination for a day of leisure and enjoyment. With its convenient location and tranquil atmosphere, this beach is a must-visit spot for anyone looking to experience the beauty of Cape Cod.

Hardings Beach is a stunning natural feature located in Chatham, Massachusetts, United States. This beautiful beach offers pristine white sand, clear blue waters, and breathtaking views of the surrounding coastline. Visitors can enjoy swimming, sunbathing, beachcombing, and picnicking at this picturesque location. Hardings Beach is the perfect spot for a relaxing day by the ocean or a romantic sunset stroll along the shore. Whether you're looking to unwind and soak up the sun or explore the natural beauty of Cape Cod, Hardings Beach is a must-visit destination.

North Beach Island is a charming tourist attraction located in Chatham, Massachusetts, United States. This picturesque island offers visitors a serene escape from the hustle and bustle of everyday life. With its pristine sandy beaches, crystal clear waters, and stunning views of the Atlantic Ocean, North Beach Island is the perfect destination for relaxation and rejuvenation. Whether you're looking to soak up the sun, go for a leisurely stroll along the shoreline, or simply take in the breathtaking scenery, North Beach Island is sure to captivate your senses and leave you feeling refreshed and renewed. Come and experience the beauty and tranquility of North Beach Island for yourself.