TOP 30 Unique vacations in Chatham, Massachusetts

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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.

Chatham Guest Rooms is a cozy lodging facility located at 1409 Main Street in the charming town of Chatham, Massachusetts. Nestled in the heart of Cape Cod, our guest rooms offer a comfortable and inviting atmosphere for travelers looking to relax and unwind. Each room is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy the convenience of being just a short walk away from the town's shops, restaurants, and beaches. Whether you're visiting for a weekend getaway or an extended vacation, Chatham Guest Rooms provides a welcoming home away from home for all travelers.

The Hong Kong is a vibrant and bustling institution located at 65 Chatham Street in Boston, Massachusetts. This popular spot is a bar, restaurant, and food establishment all rolled into one, offering a unique and exciting dining experience. With a diverse menu featuring delicious Asian cuisine and a wide selection of drinks, The Hong Kong is the perfect place to unwind with friends or enjoy a fun night out. Whether you're looking for a tasty meal, refreshing cocktails, or a lively atmosphere, The Hong Kong has something for everyone. Come visit us and see why we're a favorite destination in Boston!

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.

Welcome to An English Garden Bed & Breakfast, located at 32 Inman Road in Dennis, Massachusetts, United States. Our charming lodging institution offers a cozy and comfortable stay for guests looking to relax and unwind on Cape Cod. In the main inn, we have 9 guest rooms, each featuring a queen bed, private bathroom, climate control, and TV. Guests can enjoy the ocean views from their private balconies or decks, with some rooms overlooking our beautiful gardens in full bloom during late spring and early summer. Children under 8 years old are not allowed in guest rooms, which are accessible via stairs and sleep two guests comfortably. Complimentary breakfast is served in season from May to October.

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.

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.

Culdesac Cottage Bed and Breakfast is a charming lodging located at 49 Glover Square in the picturesque town of Chatham, Massachusetts. Situated in a peaceful cul-de-sac, this cozy cottage offers a serene and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The accommodations are tastefully decorated and feature modern amenities to ensure a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning, served in the inviting dining area. With its convenient location near beaches, shopping, and dining options, Culdesac Cottage Bed and Breakfast is the perfect choice for a memorable stay on Cape Cod.

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.

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.

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.

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.

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.