Where Should I Stay In Chatham MA?

The Captain's House Inn is a luxurious bed and breakfast, known for its romantic atmosphere and elegant English country decor. Set on two acres of beautifully landscaped gardens, it features 16 individually decorated rooms, many with fireplaces and whirlpool tubs. Guests can enjoy gourmet breakfasts, afternoon tea, and evening snacks. The inn is open year-round and is within walking distance to Chatham’s Main Street and nearby beaches, making it a popular choice for a Cape Cod getaway.

Wequassett Resort & Golf Club is a luxurious waterfront resort offering expansive views of Pleasant Bay and top-notch amenities, known for its exceptional service, the resort features elegant rooms, suites, and private cottages. Guests can enjoy dining at the signature restaurant, Twenty-Eight Atlantic, or relax at the pool overlooking the bay. The resort also boasts an 18-hole golf course, making it a prime destination for golf enthusiasts. Wequassett is open year-round, catering to both vacationers and event-goers.

Pleasant Bay Village Resort offers a tranquil setting with lush gardens, koi ponds, and a Zen-like atmosphere. The resort features a variety of accommodations, from standard rooms to suites with kitchenettes, perfect for families or couples. Amenities include a heated outdoor pool and hot tub, making it an excellent place for relaxation. While the resort is family-friendly, it also caters to guests seeking a quiet and relaxing vacation. It operates seasonally, from spring through fall.

The Chatham Motel offers a budget-friendly yet comfortable stay in a convenient location near downtown Chatham. Rooms are simple but clean, and amenities include an outdoor swimming pool, free Wi-Fi, and picnic areas. The motel is a short drive from Chatham’s beaches, shops, and restaurants, making it a practical choice for travelers who want easy access to local attractions. The motel is open year-round, offering affordable lodging for anyone exploring the Cape.

The Chatham Seafarer Inn is a charming, traditional Cape Cod inn located just a short walk from some of the region’s best beaches, including Ridgevale Beach. It's also close to the Cape Cod Rail Trail, making it an ideal base for biking and exploring the area. The inn offers a heated outdoor pool, free parking, and complimentary Wi-Fi, making it a convenient and relaxing stay for families and couples alike. Renovated and updated, the inn provides modern amenities while maintaining its classic Cape Cod appeal. Guests particularly appreciate its proximity to Chatham’s center, just a five-minute drive away, while still enjoying a peaceful and private environment​. Location. Location. Location.

Located at 49 Glover Square in Chatham, Cul-De-Sac Cottage Bed & Breakfast is a charming, privately run establishment known for its quiet, scenic setting. The innkeepers, Mike and Tina, are praised for their exceptional hospitality, ensuring that guests feel right at home. Many visitors highlight the memorable homemade breakfasts, with some guests recalling the meals fondly years later. The inn offers comfortable, spacious rooms, and good proximity to downtown Chatham and nearby beaches. Bicycles are available for guests to explore the area, and special touches such as accommodating dietary restrictions further enhance the experience. This B&B is open year-round, welcoming guests throughout all seasons​.

Chatham Bars Inn is an iconic, luxurious oceanfront resort situated on 25 acres, offering breathtaking views of the Atlantic. The property includes 217 rooms spread across elegant cottages and the main inn, with some accommodations featuring private beach access. The resort provides a wealth of amenities, including a private beach, heated pools, a spa, and fine dining restaurants. Guests can also enjoy seasonal activities such as boating, tennis, and access to the resort’s private farm. A notable dish at its celebrated restaurant is the lobster bisque, a must-try for seafood lovers. Chatham Bars Inn operates year-round, making it a top choice for both summer vacations and cozy winter getaways​.

The Hawthorne Motel offers charming, quintessential Cape Cod lodging with direct access to a private beach. Located just a short walk from Main Street, guests can enjoy both the bustling town center and the serenity of Aunt Lydia’s Cove. Rooms are cozy with a beach-inspired blue-and-white decor, and some offer kitchenettes and stunning ocean views. For those seeking more privacy, a rentable cottage sits just steps from the water and includes a full kitchen and living space. The Hawthorne is open seasonally, perfect for a summer retreat.

The Surfside Inn is a historic bed-and-breakfast located just steps away from Lighthouse Beach, offering a classic Cape Cod experience. This 23-room inn is known for its friendly service and provides a range of room styles, from cozy petite queen rooms to ocean-view suites. Guests enjoy a complimentary continental breakfast and a daily wine and cheese party on the front porch with panoramic ocean views. The inn is open seasonally, making it ideal for summer beach getaways​.

Chatham Wayside Inn is a historic boutique hotel located in the heart of downtown Chatham. With modern touches in a historic setting, this inn offers upscale amenities like a heated pool, fitness center, and dining at the Wild Goose Tavern. Its central location allows guests to walk to local shops, beaches, and galleries. Guests can enjoy spacious rooms, some with private balconies, offering views of Main Street or surrounding gardens. It operates year-round, making it a great choice for off-season getaways.

The Queen Anne Inn blends history with luxury in a charming Victorian-era building. This boutique hotel is situated within walking distance to downtown Chatham and offers individually designed rooms, many featuring four-poster beds and private balconies. The on-site restaurant provides a delightful dining experience, and the inn features a heated pool and lush gardens. It’s a tranquil and romantic option for couples, open seasonally from spring through early fall.

Formerly known as the Chatham Highlander, Greyfinch Chatham Inn underwent a modern revamp, offering a fresh and minimalist design that complements its coastal surroundings. Located a short drive from downtown Chatham and local beaches, this newly updated inn features sleek, contemporary rooms with crisp, clean lines and modern amenities. It’s a more budget-conscious option compared to some of the historic inns in the area. Greyfinch Chatham is open seasonally, primarily during the warmer months.

The Chatham Inn Relais & Châteaux is a five-star luxury inn offering an intimate and exclusive retreat with only a few rooms. It’s part of the prestigious Relais & Châteaux collection, known for its culinary excellence and refined service. The rooms are exquisitely designed with luxurious touches, and the on-site restaurant has a stellar reputation for fine dining. Guests enjoy personalized service and a prime location just steps from Chatham's shops and beaches. This inn is open year-round and is perfect for those seeking high-end accommodations and a gourmet experience.

Located in the heart of Chatham, the Old Harbor Inn is a charming and welcoming bed and breakfast with a focus on personalized service. This intimate inn offers beautifully decorated rooms, many with fireplaces, creating a cozy atmosphere. Guests can enjoy homemade breakfasts and afternoon treats in a warm, inviting setting. With just 12 rooms, the inn provides a peaceful, relaxed environment. It’s open year-round, making it a good choice for those seeking a tranquil getaway no matter the season.

The Bow Roof House is a delightful bed and breakfast set in a beautifully restored historic building. This hidden gem offers individually decorated rooms, blending antique charm with modern comforts. With its emphasis on providing a cozy, home-like experience, the Bow Roof House is ideal for travelers seeking a quiet retreat. Guests appreciate the inn’s garden setting and proximity to Chatham’s beaches and town center. This property is typically open seasonally.

Pine Shore Cottages offers classic, no-frills Cape Cod accommodations in a wooded, lakefront setting. Guests can enjoy private cottages, each featuring basic amenities like kitchenettes and outdoor spaces. The rustic charm and natural surroundings make this an ideal spot for families and those looking to experience a simpler, more relaxed Cape Cod vacation. These cottages are open seasonally, primarily in the summer months, offering a peaceful getaway.

The Chatham Guest Rooms are a small, family-owned property offering a range of accommodations, from suites to cottage-style rooms. Located just outside of Chatham's downtown, it provides a quiet, residential atmosphere while still being close to local attractions. Each room is tastefully decorated, with amenities like kitchenettes and private entrances. Guests appreciate the personal touches and attention to detail from the owners. Chatham Guest Rooms are typically open year-round, offering a cozy retreat in every season.

Elder Duck Cottages are traditional Cape Cod cottages set in a quiet, wooded location. These cottages offer a rustic, simple charm with basic amenities, making them ideal for families or those seeking a peaceful retreat. The location is perfect for exploring both the ocean and nearby ponds. Typically open during the summer season, these cottages provide a classic, relaxed Cape experience.