TOP 10 Luxury vacation accommodations in Massachusetts

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Pilgrim Beach Village is a premier real estate and travel agency located at 174 Shore Road in Truro, Massachusetts. Our agency specializes in providing luxurious beachfront properties for sale or rent, as well as personalized travel experiences for those looking to explore the beautiful Cape Cod area. With a team of experienced agents and travel experts, Pilgrim Beach Village is committed to helping clients find their dream vacation home or plan the perfect getaway. Whether you're looking for a relaxing beach retreat or an adventurous outdoor excursion, Pilgrim Beach Village has the resources and expertise to make your travel dreams a reality. Visit us today and let us help you create unforgettable memories on the stunning shores of Truro, Massachusetts.

Cape Winds Resort is a charming lodging establishment located at 657 West Main Street in Barnstable, Massachusetts, United States. Situated in a picturesque coastal town, this resort offers comfortable accommodations with stunning views of the surrounding area. Guests can enjoy a relaxing stay in well-appointed rooms, take a dip in the outdoor pool, or explore the nearby beaches and attractions. With its convenient location and friendly staff, Cape Winds Resort is the perfect destination for a memorable vacation on Cape Cod.

Simmons Homestead Inn is a charming lodging establishment located at 288 Scudder Avenue in Barnstable, Massachusetts. This historic inn offers a cozy and welcoming atmosphere for guests looking to experience the beauty of Cape Cod. The inn features comfortable rooms, delicious homemade breakfasts, and friendly hospitality from the owners. With its convenient location near beaches, shopping, and dining options, Simmons Homestead Inn is the perfect choice for a relaxing getaway in Cape Cod.

Pelham on Earle is a charming lodging institution situated at 30 Earle Road in the picturesque town of Harwich, Massachusetts. This cozy retreat offers a peaceful and serene atmosphere, perfect for a relaxing getaway. The rooms are tastefully decorated and equipped with all the necessary amenities to ensure a comfortable stay. Guests can enjoy the beautiful surroundings and explore the nearby beaches and attractions. Whether you are looking for a romantic escape or a family vacation, Pelham on Earle is the ideal choice for a memorable stay in Cape Cod.

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.

The Inn on the Beach is a charming lodging located at 16 Bank Street in Harwich, Massachusetts, United States. Situated right on the beach, this cozy inn offers guests a peaceful and relaxing retreat with stunning ocean views. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast in the morning and spend their days lounging on the sandy shores or exploring the nearby attractions. Whether you're looking for a romantic getaway or a family vacation, the Inn on the Beach is the perfect destination for a memorable stay by the sea.

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.

A Beach Breeze Inn is a charming lodging located at 169 Massachusetts 28, in the picturesque town of Harwich, Massachusetts. This cozy inn offers comfortable accommodations just a short walk away from the beach, allowing guests to enjoy the soothing sounds of the ocean and the refreshing sea breeze. The inn provides a relaxing atmosphere, perfect for a peaceful getaway or a romantic retreat. With its convenient location and welcoming ambiance, A Beach Breeze Inn is the ideal choice for those looking to unwind and rejuvenate by the sea.

Harwichport Resort Club is a charming lodging institution located on Main Street in the picturesque town of Harwich, Massachusetts. Nestled in the heart of Cape Cod, this resort offers comfortable accommodations and a relaxing atmosphere for guests looking to unwind and enjoy the beauty of the surrounding area. With its convenient location near the beach, shopping, and dining options, Harwichport Resort Club is the perfect destination for a weekend getaway or a longer vacation. Come experience the hospitality and charm of this lovely resort in the heart of 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.

The Mooring at Harwich Port is a charming lodging facility located at 525 Massachusetts 28 in the picturesque town of Harwich, Massachusetts, United States. This cozy retreat offers guests a peaceful and comfortable stay, with well-appointed rooms, friendly staff, and a convenient location near the beautiful beaches and attractions of Cape Cod. Whether you are seeking a relaxing getaway or a fun-filled vacation, The Mooring at Harwich Port is the perfect place to rest and rejuvenate.

Wychmere Beach Club is a luxurious lodging institution located at 23 Snow Inn Road in Harwich, Massachusetts, United States. Nestled on the shores of Cape Cod, this beachfront resort offers stunning views of the ocean and a tranquil atmosphere for guests to relax and unwind. The club features elegant accommodations, fine dining options, and a range of amenities including a private beach, swimming pools, and a spa. Whether you're looking for a romantic getaway or a family vacation, Wychmere Beach Club provides the perfect setting for a memorable stay by the sea.

Located on 300 feet of private beachfront overlooking the Nantucket Sound in Dennis Port, MA, Edgewater Beach Resort offers a fully renovated 76-room resort for year-round enjoyment. Whether you're looking for a summer escape or a cozy winter retreat, Edgewater Beach Resort has something for everyone. Vacation ownership options allow guests to return to the same unit each year or explore other locations through exchange partners. The resort prides itself on ongoing maintenance and renovations to ensure a relaxing and enjoyable experience for all guests.

Located at 327 South Shore Drive in Yarmouth, Massachusetts, the Riviera Beach Resort is a charming lodging institution that offers guests a relaxed and joyful oceanfront experience. Families can enjoy the sprawling private beach, endless activities, and convenient adjoining rooms and spacious suites. Children can build sandcastles on the private beach while parents soak in the sun. With kid-friendly amenities and a world of beach adventures, families can create timeless memories. The resort is known for its proximity to beautiful beaches and quiet residential neighborhoods, offering stunning coastline views and iconic New England seafaring scenes. The beachfront location provides clear ocean views and an open invitation to dive in, bask, and treasure hunt along the enchanting coastline. The resort offers 125 thoughtfully designed guest rooms, from tranquil poolside retreats to ocean view rooms with breathtaking vistas. Guests can enjoy dining options by the pool, at the waterfront bar, or in the dining room, all featuring the classic taste of New England cuisine.

The Beauport Inn is a charming lodging establishment located at 37 Main Street in the picturesque town of Rockport, Massachusetts. This cozy inn offers comfortable accommodations and friendly service in a beautiful seaside setting. Guests can enjoy a relaxing stay just steps away from the beach and a short walk from the town's shops, restaurants, and attractions. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, the Beauport Inn is the perfect choice for your stay in Rockport.

The Shady Hollow Inn is a charming lodging establishment located at 370 Main Street in Dennis, Massachusetts, United States. Nestled in a tranquil and picturesque setting, this cozy inn offers a peaceful retreat for travelers seeking a relaxing getaway. Guests can enjoy comfortable accommodations, friendly service, and a warm atmosphere that makes them feel right at home. Whether you're visiting for a weekend escape or an extended vacation, The Shady Hollow Inn is the perfect place to unwind and recharge in the heart of Cape Cod.

Riverview Resort is a charming lodging establishment situated at 37 Neptune Lane in the picturesque town of Yarmouth, Massachusetts. Nestled along the banks of a tranquil river, this resort offers guests a peaceful and serene retreat surrounded by nature. The resort features comfortable accommodations, a variety of amenities, and stunning views of the river from many of the rooms. Whether you're looking for a relaxing getaway or a fun-filled vacation, Riverview Resort is the perfect destination for travelers seeking a memorable experience in the United States.

The Beach House at Bass River is a charming lodging facility located at 73 South Shore Drive in Yarmouth, Massachusetts. Situated right by the beautiful Bass River, this institution offers guests a peaceful and relaxing retreat by the water. With cozy rooms and stunning views of the river, guests can enjoy a tranquil stay while being just a short drive away from the bustling town center. Whether you're looking for a romantic getaway or a family vacation, the Beach House at Bass River provides the perfect setting for a memorable stay on the Cape.

Blue Water Resort, located at 291 South Shore Drive in Yarmouth, Massachusetts, is a vibrant beachfront getaway for those seeking joyful thrills and memorable experiences. Nestled on the Nantucket Sound, this resort offers a range of activities from boogie boarding to enjoying delicious lobster rolls and colorful drinks at the beachside tiki bar. With its enviable location steps away from the shore, guests can indulge in sunrise strolls, afternoon dips, and sunset walks on the beach. The resort's South Yarmouth location on South Shore Drive offers picturesque views, sandy beaches, and a taste of the coastal lifestyle. Guests can choose from a variety of accommodations, including dog-friendly rooms, family suites, and chic accessible rooms. With access to the beaches, pools, and activities at all properties, including the nearby Riviera Beach Resort, guests can truly make the most of their Cape Cod adventure.

Red Jacket Beach Resort & Spa is a luxurious lodging institution located at 1 South Shore Drive in Yarmouth, Massachusetts, United States. Nestled along a pristine private shoreline, the resort is the flagship property of a collection that offers spacious rooms and vacation cottages perfect for couples, groups, and anyone seeking a Cape Cod experience filled with coastal comforts. Situated by the beautiful banks of Parker's River in South Yarmouth, Red Jacket Beach Resort boasts panoramic vistas that combine the expansive beauty of the ocean with the picturesque sights of the river. As the central hub for indulgence and notable amenities, the resort offers unparalleled hospitality and a curated menu of distinctive treatments at the on-site spa.

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 Villages at Ocean Edge is a luxurious lodging destination situated at 1 Villages Drive in the charming town of Brewster, Massachusetts. This upscale resort offers a range of accommodation options, from spacious villas to cozy guest rooms, all designed with modern amenities and elegant decor. Guests can enjoy access to a variety of on-site facilities, including multiple swimming pools, a fitness center, tennis courts, and a private beach. The resort also boasts several dining options, a spa, and a golf course, making it the perfect retreat for a relaxing getaway or special occasion. With its picturesque location on Cape Cod, The Villages at Ocean Edge offers a tranquil and idyllic setting for a memorable stay.

The Pepper House Inn is a charming lodging establishment located at 2062 Main Street in Brewster, Massachusetts. This historic inn offers a cozy and comfortable atmosphere for guests to relax and unwind during their stay on Cape Cod. The inn features beautifully appointed rooms, a delicious breakfast served each morning, and a convenient location near local attractions and beaches. Whether you are looking for a romantic getaway or a peaceful retreat, the Pepper House Inn is the perfect destination for your next vacation.

Ocean Edge Resort & Golf Club is a luxurious lodging institution located at 2907 Main Street in Brewster, Massachusetts, United States. With activities aplenty, convenient location, and exceptional service, guests can enjoy a truly unforgettable experience. From the turn-of-the-century Nickerson Mansion to multi-bedroom villas, our accommodations cater to every need. Whether you're looking for a relaxing beach vacation or an adventurous getaway, Ocean Edge has something for everyone. Guests can enjoy a range of activities including paddleboarding, biking, oyster bed tours, and more. Military personnel can take advantage of special discounts, while gift cards make for the perfect present for loved ones. Indulge in a spa treatment, savor a meal at one of our fine restaurants, or hit the links at the Ocean Edge Golf Club.

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.

The Soundings Seaside Resort is a charming lodging located at 59 Chase Avenue in Dennis, Massachusetts, United States. Situated right by the beach, this resort offers guests stunning ocean views and easy access to the sand and surf. The accommodations are cozy and comfortable, providing a relaxing retreat for visitors looking to unwind by the sea. With impeccable service and a range of amenities, The Soundings Seaside Resort is the perfect destination for a seaside getaway.

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.

Located in the charming town of Dennis, Massachusetts, Joy House Bed & Breakfast offers a cozy and welcoming atmosphere for guests seeking a relaxing getaway. Situated at 181 Depot Street, this quaint lodging establishment provides comfortable accommodations and personalized service to ensure a memorable stay. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions such as Cape Cod beaches, restaurants, and shops. Whether you are looking for a romantic retreat or a family vacation, Joy House Bed & Breakfast is the perfect destination for a peaceful escape.

Bluegreen The Breakers Resort is a charming lodging establishment located at 61 Chase Avenue in Dennis, Massachusetts. This beautiful resort offers a peaceful retreat for guests looking to relax and unwind by the ocean. The resort features comfortable accommodations, stunning ocean views, and top-notch amenities such as a swimming pool, fitness center, and on-site dining options. Whether you're looking for a romantic getaway or a fun family vacation, Bluegreen The Breakers Resort is the perfect choice for your next trip to the Cape Cod area.

The Conch Inn is a charming lodging establishment located at 423 Lower County Road in Dennis, Massachusetts. Nestled in the heart of Cape Cod, this cozy inn offers guests a peaceful and relaxing retreat just minutes away from the beach. With comfortable accommodations, friendly staff, and a convenient location, The Conch Inn is the perfect choice for those looking to experience the beauty and charm of Cape Cod. Whether you're visiting for a weekend getaway or an extended vacation, The Conch Inn welcomes you with open arms and a warm, inviting atmosphere.