TOP 30 Vacation getaway in Chatham, Massachusetts

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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.

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 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.

The Chatham Seafarer Inn, located at 2079 Main Street in Chatham, Massachusetts, is a charming lodging option for your Cape Cod vacation. Just a short walk from the best beaches in Cape Cod and steps away from the Cape Cod Rail Trail bike path, this inn offers a relaxing retreat with a heated swimming pool for guests to enjoy. With easy access to the center of historic Chatham, as well as a variety of dining options nearby, the Chatham Seafarer is the perfect choice for your Cape Cod getaway. Recently renovated and fully updated, this inn combines traditional Cape Cod charm with modern comforts to ensure a memorable stay for you and your family. Experience the best of Chatham at the Chatham Seafarer Inn.

Chatham Motel is a charming lodging establishment located at 1487 Main Street in the picturesque town of Chatham, Massachusetts. This cozy motel offers comfortable rooms and excellent amenities for a relaxing stay on Cape Cod. Conveniently situated near the town center, guests can easily explore the local shops, restaurants, and attractions. Whether you're visiting for a weekend getaway or an extended vacation, Chatham Motel provides a warm and welcoming atmosphere for all travelers. Enjoy a peaceful retreat in this beautiful coastal town at Chatham Motel.

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.

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.

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.

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 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.

Looking to relax in South Chatham? Look no further than this clean, comfortable, and convenient institution located at 24 Myrtle Drive in Chatham, Massachusetts. Whether you're looking for a vacation rental or a new home, this real estate and travel agency has you covered. With a focus on providing top-notch service and accommodations, you can trust that your stay in South Chatham will be a relaxing and enjoyable experience. Visit us today to find your perfect 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.

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.

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.

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.

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.

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.

The Hawthorne Motel is a charming lodging establishment located at 196 Shore Road in the picturesque town of Chatham, Massachusetts. Nestled in a tranquil coastal setting, this motel offers comfortable accommodations and a relaxing atmosphere for guests looking to unwind and enjoy the beauty of Cape Cod. With its convenient location near the beach and local attractions, the Hawthorne Motel is the perfect destination for a peaceful getaway or a memorable vacation experience. Whether you're seeking a romantic retreat or a family-friendly escape, this welcoming institution provides a cozy and inviting setting for all travelers to enjoy.

The Inn at the Oaks is a charming 13 room Inn located in Cape Cod's historic Eastham, Massachusetts. Our spacious and light-filled accommodations, delicious continental breakfasts, and attention to detail ensure that your Cape Cod vacation will be unforgettable. Situated across from the National Seashore Visitor Center and close to world-famous beaches, the Cape Cod Rail Trail, and historic towns like Chatham, Orleans, Wellfleet, and Provincetown, the Inn offers a perfect location for exploring the best of Old Cape Cod. Many guests consider the Inn their "home" on the Cape and return year after year. Children over the age of 10 are welcome, but please note that our property is not wheelchair accessible. Book 3 nights or more mid-week from March 1 to April 30 and save 10% on your entire stay when booking directly with the Inn using the code SPRING10. Come and experience the beauty and charm of Cape Cod at the Inn at the Oaks.

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.

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.

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.

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.

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!