The 30 Best Luxury guest rooms in Chatham, Massachusetts

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.

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.

Surfside Inn Chatham is a charming lodging located at 25 Holway Street in the picturesque town of Chatham, Massachusetts. Situated just a short walk away from the beautiful beaches of Cape Cod, this inn offers guests a relaxing and comfortable stay in a serene coastal setting. The well-appointed rooms feature modern amenities and cozy furnishings, providing a home away from home for visitors. With its convenient location near local shops, restaurants, and attractions, Surfside Inn Chatham is the perfect choice for a peaceful getaway on the Cape.

Greyfinch Chatham Inn, located at 946 Main Street in Chatham, Massachusetts, is a lodging institution that welcomes adventurous travelers, friends, young families, and couples to enjoy a seaside oasis. The newly renovated Greyfinch offers elegantly transformed guestrooms and enhanced outdoor spaces, providing a tranquil retreat just minutes away from Chatham's best beaches and downtown shops and restaurants. Guests can indulge in the allure of elegant accommodations that exude a welcoming atmosphere, making them feel right at home. The inn also offers luxury amenities for a truly indulgent stay. The property is steeped in Chatham's rich history of fishing, farming, seafaring, and hospitality, giving guests a glimpse into local life on the Cape.

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 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 Spa at Chatham Bars Inn is a luxurious retreat located at 297 Shore Road in Chatham, Massachusetts. Step into a world of transformation and relaxation with treatments designed to soothe and restore your body, mind, and soul. As the only Forbes Four-Star awarded spa on Cape Cod, MA, we offer everything you need to completely unwind and recharge. Our spa amenities, including a pool, steam room, sauna, and hot tub, are available for guests with spa appointments or those staying in a spa suite. The spa is reserved for guests 16 years of age and older. To reserve your treatment, call 508-945-6737 or book online.

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.

The Captain's House Inn is a charming lodging located at 369 Old Harbor Road in the picturesque town of Chatham, Massachusetts. This historic inn offers a cozy and luxurious stay for guests looking to experience the beauty of Cape Cod. With elegantly decorated rooms, delicious breakfast options, and personalized service, the Captain's House Inn provides a memorable and relaxing getaway for visitors to the United States.

A Little Inn on Pleasant Bay is a charming and romantic boutique Bed & Breakfast located in Orleans, Massachusetts. Winner of the 2023 LuxLife Hospitality Awards for Most Charming Bed & Breakfast in MA, our inn offers guests quintessential European hospitality in an all-American setting. Situated between the historic villages of Chatham and Orleans on Cape Cod, our nine-room inn overlooks the picturesque Pleasant Bay. Each room is named after sailboats that sail the waters of Cape Cod, with a strong New England identity and beautifully designed by interior designer Matthew Yee.

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 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.

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.

Welcome to The North End – Italian Neighborhood, your ultimate guide to experiencing the vibrant heart of Boston’s “Little Italy.” Nestled at 14 North Square in Boston, Massachusetts, this charming enclave is a captivating blend of rich history, diverse culture, and exquisite cuisine. Whether you're a local or a visitor, The North End offers a delightful journey through time and taste. Discover the allure of the North End, one of Boston's oldest residential areas, where the echoes of early European settlers mingle with the lively spirit of Italian immigrants. As you stroll through its narrow streets, you'll be greeted by rustic Italian street signs and the irresistible aroma of authentic Italian cuisine emanating from over 100 restaurants, cafés, and bakeries. From traditional dishes to innovative culinary delights, the North End is a paradise for food lovers.