Historical inn with breakfast in Chatham, Massachusetts

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.

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.

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.

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.

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.

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 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.

Queen Anne Inn Cafe & Lounge is a charming and inviting establishment located at 70 Queen Anne Road in the picturesque town of Chatham, Massachusetts. This institution offers a unique combination of a cozy cafe, a delicious restaurant, and comfortable lodging all in one place. Whether you are looking for a relaxing breakfast, a satisfying lunch, or a gourmet dinner, Queen Anne Inn Cafe & Lounge has something to offer for everyone. The lounge area provides a cozy atmosphere where guests can enjoy cocktails, wine, and appetizers. With its warm and welcoming ambiance, this institution is the perfect spot for a casual meal or a special occasion. Come and experience the charm of Queen Anne Inn Cafe & Lounge in the heart of Chatham.

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.

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.

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.