TOP 10 Best Luxury escape in Chatham, Massachusetts

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.

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 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.

Lower Cape Escape is a premier real estate and travel agency located in Chatham, Massachusetts. Situated at 247 Morton Road, this institution specializes in providing luxurious vacation rentals and properties for sale in the Lower Cape Cod area. Whether you are looking for a cozy beachfront cottage or a spacious family home, Lower Cape Escape offers a wide range of options to suit every taste and budget. With their expert knowledge of the local real estate market and dedication to customer satisfaction, Lower Cape Escape is your go-to destination for all your vacation rental and property buying needs in Cape Cod.

Queen Anne Luxury Townhouses is a prestigious real estate agency located at 70 Queen Anne Road in Chatham, Massachusetts. Our townhouses offer the epitome of luxury living, with modern amenities and stunning architecture. Each townhouse is meticulously designed to provide the ultimate in comfort and style. Nestled in the charming town of Chatham, our properties offer a tranquil escape while still being conveniently located near shops, restaurants, and the beach. Experience the height of elegance and sophistication at Queen Anne Luxury Townhouses.

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.

Cape Cod Catamaran Sailing Charters is a travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States. Offering morning and afternoon charters as well as sunset cruises from Wellfleet Harbor, this institution provides an authentic Cape Cod experience on their catamaran, Discovery. Escape the crowds and immerse yourself in the serene beauty of Cape Cod with a private daytime charter, where you can explore the bay, watch seals, or simply relax and enjoy the tranquility of the local waters. The experienced captain ensures a smooth and comfortable ride as you navigate Wellfleet Harbor and Cape Cod Bay.

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.

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.

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.

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.

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.

Colibri Spa is a tranquil oasis located at 60E Munson Meeting Way in Chatham, Massachusetts. Our luxurious spa offers a wide range of rejuvenating treatments and services to help you relax, unwind, and pamper yourself. From massages and facials to body wraps and scrubs, our experienced therapists are dedicated to providing you with a truly indulgent spa experience. Whether you're looking to escape the stresses of everyday life or simply treat yourself to some well-deserved self-care, Colibri Spa is the perfect destination for all your relaxation needs. Come visit us and discover the ultimate in relaxation and rejuvenation.

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.

Pleasant Forest Shores cottages is a charming lodging establishment located at 259 Pleasant Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a tranquil forest setting, the cottages offer a peaceful retreat for guests looking to escape the hustle and bustle of everyday life. Each cottage is tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the serene surroundings, take a leisurely stroll to the nearby beach, or explore the quaint shops and restaurants in the town center. Whether you are seeking a romantic getaway or a family vacation, Pleasant Forest Shores cottages provide the perfect setting for a relaxing and rejuvenating experience.

The Priscilla House is a charming lodging establishment located at 388 Main Street in the picturesque town of Chatham, Massachusetts. This historic house offers a cozy and welcoming atmosphere for guests to relax and unwind during their stay on Cape Cod. With comfortable accommodations and a convenient location near local attractions and amenities, The Priscilla House is the perfect choice for a memorable getaway in the United States.

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.