TOP 10 Best Unique vacation packages in Chatham, Massachusetts

Chatham Inn is a luxurious institution located at 359 Main Street in Chatham, Massachusetts, United States. This establishment offers a unique experience, being Cape Cod’s only Relais & Châteaux and Forbes Five-Star hotel. Renovated between 2016 and 2019, Chatham Inn seamlessly blends modern decor, top-notch amenities, and exceptional service with the rich history of the oldest inn on the Cape. It has been recognized as one of the top hotels for service and romance in the United States, as well as being rated the number one hotel in Chatham and Cape Cod. The 18 beautifully renovated guest rooms and suites at Chatham Inn feature modern luxuries while preserving the inn's historic charm. Guests can choose from twin, queen, or king bed options, as well as spacious Premier King Rooms or Suites with private balconies, fireplaces, and wet bars. A Chef’s à la carte Breakfast is included in the stay, served in the elegant dining room.

Located at 512 Main Street in Chatham, Massachusetts, the Chatham Wayside Inn is a unique lodging option that combines a contemporary feel with exceptional service. This boutique hotel offers a restful retreat with amenities such as a heated pool and fitness center. Each room and suite has been carefully restored and offers a different look, with spacious rooms and upscale amenities. Guests can relax on the patio or private balcony and enjoy the sea air. The hotel staff, who are locals, are happy to share their knowledge of the historic town and nearby attractions. Special packages, such as the Birthday & Anniversary package and the Month of Love Package, offer guests the opportunity to enhance their stay with added perks. Don't miss out on the Leap Into Savings promotion, which includes savings of up to 15% and a $50 Food and Beverage credit. Whether you're visiting in the spring, summer, fall, or winter, the Chatham Wayside Inn has something to offer for every season. Book your stay now and experience the charm of this historic hotel in Cape Cod.

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.

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.

The Old Harbor Inn is a charming lodging establishment located at 22 Old Harbor Road in the picturesque town of Chatham, Massachusetts. Nestled in a tranquil and historic setting, this inn offers guests a cozy and welcoming atmosphere with comfortable accommodations. Whether you are looking for a romantic getaway or a relaxing retreat, The Old Harbor Inn provides the perfect home away from home. With its convenient location near the harbor and local attractions, guests can easily explore the beauty and charm of Chatham. Experience exceptional hospitality and personalized service at The Old Harbor Inn for a memorable stay in Cape Cod.

Monomoy Sportfishing is a premier destination for anglers of all skill levels, located at Ryder's Cove Road in picturesque Chatham, Massachusetts. As a top-rated sportfishing school, tourists and locals alike can experience the thrill of deep sea fishing in the beautiful waters off the coast of Cape Cod. With experienced guides and state-of-the-art equipment, Monomoy Sportfishing offers a unique and unforgettable fishing experience for all who visit. Whether you're a seasoned angler looking to hone your skills or a beginner hoping to reel in your first big catch, Monomoy Sportfishing is the perfect destination for your next fishing adventure.

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.

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.

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.

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.

Hyannis Harbor Tours Inc dba Cape Cod Custom Tours is a premier travel agency located at 36 Ocean Street in Barnstable, Massachusetts. Specializing in personalized tours of the beautiful Cape Cod region, our experienced guides will take you on a journey through the area's rich history, stunning landscapes, and charming seaside towns. Whether you're looking to explore the historic sites of Hyannis Harbor, relax on the sandy beaches of Provincetown, or sample fresh seafood in Chatham, our custom tours cater to your specific interests and preferences. Embark on an unforgettable adventure with Cape Cod Custom Tours and discover the beauty and charm of Cape Cod like never before.