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Check prices for these dates, December 13 – 14, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stroll the historic Main Street lined with boutiques, then head to Lighthouse Beach for seal-spotting at low tide. Seafood shacks serve the freshest catch, while the Chatham Bandstand hosts free summer concerts that locals never miss.
Prices for B&Bs in Chatham often vary, but you can find a great deal from $242 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chatham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
Old Harbor Inn in Chatham is an excellent choice for families seeking a cozy getaway. With its spacious rooms featuring a convenient sofa bed, this property ensures everyone has a comfortable place to unwind. Guests can enjoy daily housekeeping and a complimentary buffet breakfast, superb for fueling up before a day of adventure. The inn also offers delightful amenities like private picnic areas and a serene garden, making it a lovely spot for families to relax together.
Another fantastic option is Surfside Inn Chatham, which caters specifically to families with children. This charming B&B provides free amenities for kids, including cribs and child-friendly window designs that prioritize safety. The friendly setting and thoughtful touches make it an ideal base for families looking to create lasting memories while enjoying the beautiful surroundings of Chatham.
Captain's House Inn is a charming option for travelers in Chatham who wish to bring their furry friends along. This inviting property not only welcomes service animals but also offers a range of delightful amenities designed to enhance your stay. Guests can enjoy a complimentary full breakfast each morning, featuring local flavors, and unwind in rooms adorned with premium bedding, designer toiletries, and cozy fireplaces, superb for creating memorable moments with family or friends.
Another excellent choice is Surfside Inn Chatham, which also accommodates service animals. Located just steps from the pristine beach, this B&B provides direct access to white sand shores, making it an ideal spot for families looking to enjoy sun-soaked days by the ocean. The property features child-friendly window designs and offers complimentary cribs and breakfast for children, ensuring that little ones are well taken care of. Guests can also take advantage of free self-parking and in-room WiFi, making it convenient for families on the go.
For couples seeking a romantic getaway, the Old Harbor Inn in Chatham, MA, is a delightful choice that exudes charm and intimacy. This enchanting bed and breakfast offers a variety of thoughtful amenities designed to enhance your stay, including complimentary buffet breakfast, which sets a lovely tone for your mornings together.
The best time to book a B&B in Chatham is during the summer months, particularly from June to August. This vibrant season attracts travelers eager to enjoy the picturesque beaches, charming coastal scenery, and a variety of outdoor activities. With warm temperatures averaging in the low 70s to mid-80s Fahrenheit, it's an ideal time for beach outings, sailing, and exploring local attractions.
July stands out as the peak month for visitors, bringing an energetic atmosphere filled with festivals, farmers' markets, and an array of water sports. The lively ambiance allows guests to fully immerse themselves in the community spirit and enjoy the best of what Chatham has to offer.
For those looking for a more budget-friendly option, consider planning your trip in late September or early October. During this shoulder season, the weather remains pleasant, with temperatures still hovering in the comfortable 60s to low 70s Fahrenheit, and the crowds begin to thin. This is a wonderful time to enjoy the natural beauty of Chatham while taking leisurely strolls along the coast or savoring local seafood without the hustle and bustle of peak tourist months.
Every Chatham B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chatham B&Bs.