TOP 10 Luxury vacation accommodations in Massachusetts

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Kingfisher Oceanside is a charming lodging institution located at 15 Sea Street in Dennis, Massachusetts, United States. Situated right by the ocean, guests can enjoy stunning views and easy access to the beach. The cozy rooms are tastefully decorated and equipped with modern amenities for a comfortable stay. The friendly staff is always ready to assist guests and ensure a memorable experience. Whether you're looking for a relaxing getaway or a fun-filled vacation by the sea, Kingfisher Oceanside is the perfect choice for your accommodation needs.

Bluebird Dennisport is a charming lodging located at 426 Lower County Road in Dennis, Massachusetts. This cozy retreat offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind on Cape Cod. With its convenient location near the beach and local attractions, Bluebird Dennisport is the perfect place to enjoy a peaceful getaway in the heart of New England. Whether you're seeking a romantic weekend escape or a family vacation, Bluebird Dennisport provides a home away from home for all travelers.

The Ebb Tide Cottages is a charming lodging option located at 88 Chase Avenue in Dennis, Massachusetts, United States. Nestled near the picturesque coastline, this institution offers cozy and comfortable cottages for guests to enjoy a relaxing getaway by the sea. With its serene atmosphere and convenient location, The Ebb Tide Cottages is the perfect destination for those seeking a peaceful retreat on Cape Cod.

Safe Harbor Bed & Breakfast Cape Cod is a charming institution located at 647 Main Street in Harwich, Massachusetts. This cozy bed and breakfast offers a peaceful retreat for travelers looking to escape the hustle and bustle of everyday life. With comfortable and inviting accommodations, guests can relax and unwind in a serene setting. The on-site cafe serves delicious food and beverages, making it the perfect spot to start your day or enjoy a leisurely meal. Whether you're exploring the beautiful beaches of Cape Cod or simply looking for a quiet place to relax, Safe Harbor Bed & Breakfast is the ideal destination for your next getaway.

Brewster Green Resort is a charming lodging establishment located at 203 Lund Farm Way in Brewster, Massachusetts. As a unique combination of a resort, real estate agency, and travel agency, Brewster Green offers luxurious accommodations, expert real estate services, and personalized travel planning all in one convenient location. Whether you're looking for a relaxing getaway, a new property investment, or assistance with planning your next vacation, Brewster Green Resort has everything you need to make your stay in Brewster unforgettable.

Cape Cod Ocean Manor is a charming lodging establishment located at 543 Ocean Street in Barnstable, Massachusetts, United States. Situated just steps away from the beautiful shores of Cape Cod, this cozy retreat offers guests a peaceful and relaxing stay. The Manor features comfortable accommodations, stunning ocean views, and convenient access to local attractions and activities. Whether you're seeking a romantic getaway or a family vacation, Cape Cod Ocean Manor is the perfect destination for a memorable stay on the Massachusetts coast.

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 Old Manse Inn is a charming and historic bed and breakfast located at 1861 Main Street in Brewster, Massachusetts. This cozy inn offers a warm and welcoming atmosphere, with beautifully decorated rooms and exceptional hospitality. Guests can enjoy a delicious homemade breakfast each morning, relax in the peaceful garden, or explore the nearby beaches and attractions of Cape Cod. Whether you're looking for a romantic getaway or a relaxing retreat, the Old Manse Inn is the perfect choice for your stay in Brewster.

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.

Located on the picturesque Cape Cod in Harwich, Massachusetts, Wequassett Resort & Golf Club is a luxurious lodging institution that offers a unique blend of upscale accommodations, world-class dining, and stunning views of the Atlantic Ocean. The resort features lavish rooms and suites, a championship golf course, a private beach, and a variety of activities for guests to enjoy. With impeccable service and attention to detail, Wequassett Resort & Golf Club is the perfect destination for those seeking a relaxing and indulgent getaway on the East Coast of the United States.

Candleberry Inn Cape Cod Bed and Breakfast is a charming and cozy establishment located on Main Street in Brewster, Massachusetts. This historic inn offers comfortable accommodations and a warm, inviting atmosphere for guests looking to relax and unwind on Cape Cod. The inn features beautifully decorated rooms, a delicious breakfast served each morning, and a restaurant offering delectable meals made with locally sourced ingredients. Whether you are visiting for a romantic getaway or a family vacation, Candleberry Inn is the perfect choice for a memorable stay on the Cape.

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.

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.

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.

The Wade Cottages offer charming and cozy accommodations in the heart of Nantucket, Massachusetts. Located at 35 Shell Street, this quaint lodging option provides a peaceful and relaxing atmosphere for guests to enjoy their stay on the island. The cottages are tastefully decorated and equipped with all the amenities needed for a comfortable and enjoyable vacation. Whether you're looking for a romantic getaway or a family-friendly retreat, The Wade Cottages are the perfect choice for your stay in Nantucket.

Holly Tree Resort is a charming lodging institution located at 412 Massachusetts 28, Yarmouth, Massachusetts. Situated in the United States, this resort offers cozy accommodations and a range of amenities to ensure a comfortable stay for guests. With its convenient location near popular attractions and beautiful beaches, Holly Tree Resort is the perfect destination for a relaxing getaway. Whether you're looking to unwind by the pool, explore the local area, or simply enjoy some time away from the hustle and bustle of everyday life, this resort has everything you need for a memorable vacation.

Atlantic Oaks RV Resort is a one-stop destination for all your camping and RV needs in Eastham, Massachusetts. Located at 3700 U.S. 6, this sprawling resort offers a campground, car repair services, lodging accommodations, a park for outdoor activities, RV park for convenient parking, storage facilities for your belongings, and a store for all your camping essentials. Whether you're looking to relax in nature, explore the Cape Cod area, or simply enjoy a comfortable stay in your RV, Atlantic Oaks RV Resort has everything you need for a memorable vacation experience.

Harbor Village Cottages is a charming lodging institution located at 160 Marston Avenue in Barnstable, Massachusetts, United States. Nestled in a picturesque coastal town, Harbor Village Cottages offers cozy and comfortable accommodations for guests looking to relax and unwind by the sea. Each cottage is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy the tranquil surroundings, explore the nearby beaches and attractions, or simply take in the beautiful views of the harbor. Whether you're planning a romantic getaway or a family vacation, Harbor Village Cottages provides a peaceful retreat for all travelers.

Heritage House Inn is a charming lodging establishment located at 540 Old Colony Road in Barnstable, Massachusetts. This cozy inn offers a peaceful and relaxing retreat for guests looking to experience the historic charm of Cape Cod. With comfortable accommodations, friendly staff, and convenient amenities, Heritage House Inn is the perfect choice for a memorable stay in this beautiful coastal town. Whether you are visiting for a weekend getaway or an extended vacation, you will feel right at home at Heritage House Inn.

Rugosa Boutique Guest House is a charming lodging establishment located in Eastham, Massachusetts, United States. Situated at 4885 U.S. 6, this boutique guest house offers a cozy and intimate atmosphere for guests looking for a peaceful retreat on Cape Cod. The beautifully decorated rooms and personalized service make it a perfect choice for those seeking a relaxing getaway. With its convenient location and comfortable accommodations, Rugosa Boutique Guest House is the ideal place to stay while exploring the natural beauty and attractions of the Cape Cod area.

Nauset Beach Inn is a charming lodging establishment located at 237 Beach Road in Orleans, Massachusetts. Situated just a short walk away from the picturesque Nauset Beach, this inn offers cozy and comfortable accommodations for visitors looking to enjoy a relaxing getaway on Cape Cod. With its convenient location, guests can easily explore the nearby attractions, shops, and restaurants. The inn provides a warm and welcoming atmosphere, making it the perfect place to unwind after a day of beachcombing or sightseeing. Whether you're looking for a romantic escape or a family vacation, Nauset Beach Inn is the ideal choice for your stay in Orleans.

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 Beach Plum Motor Lodge is a charming lodging establishment located in Eastham, Massachusetts, United States. Situated at 2555 U.S. 6, this cozy motor lodge offers comfortable accommodations for travelers looking to explore the Cape Cod region. The lodge is just a short drive away from popular attractions such as the Cape Cod National Seashore and the historic town of Provincetown. Guests can enjoy spacious rooms, friendly service, and a convenient location near the beach. Whether you're visiting for a relaxing getaway or a fun-filled vacation, the Beach Plum Motor Lodge is the perfect place to stay.

Fort Hill Bed and Breakfast offers a charming ocean-view cottage located at 75 Fort Hill Road in Eastham, Massachusetts. This cozy lodging option provides guests with a peaceful and picturesque retreat, perfect for those looking to relax and unwind by the sea. The cottage is well-appointed with comfortable furnishings and modern amenities, ensuring a comfortable stay for all visitors. Guests can enjoy stunning views of the ocean from the property, as well as easy access to nearby attractions such as the Cape Cod National Seashore and local restaurants and shops. Whether you're seeking a romantic getaway or a quiet escape, Fort Hill Bed and Breakfast's ocean-view cottage is the perfect choice for your next vacation.

Captains Quarters is a charming lodging establishment located at 5000 U.S. 6 in Eastham, Massachusetts. This quaint inn offers cozy accommodations with a nautical theme, perfect for those looking for a relaxing and comfortable stay on Cape Cod. The rooms are tastefully decorated and equipped with modern amenities to ensure a pleasant stay for guests. With its convenient location near the beach and other attractions, Captains Quarters is the ideal choice for travelers seeking a peaceful retreat in a picturesque setting. Whether you're visiting for a weekend getaway or an extended vacation, this welcoming inn provides a warm and inviting atmosphere for all guests.

The Seagrove is a charming lodging establishment located at 25 Seaview Road in Eastham, Massachusetts, United States. Situated near the coast, guests can enjoy beautiful views and easy access to the beach. The Seagrove is proud to offer a 10% discount to active and retired Military as a token of appreciation for their service. Proof of service is required and the discount cannot be combined with any other offer. Come stay at The Seagrove for a relaxing and memorable getaway by the sea.

Kingfisher Lodging is a pet-friendly accommodation located at 177 Main Street in Dennis, Massachusetts. Since 2001, the Fisher family has been welcoming guests to this historic property on Cape Cod. The recently renovated motel is just a short drive from some of the finest beaches, restaurants, and attractions in the area. Guests can relax at the outdoor pool, one of the largest in the region, or take their four-legged friend to the fenced-in dog run. The hotel prides itself on being one of the few pet-friendly options on Cape Cod.

Aunt Sukie Bed and Breakfast is a charming lodging establishment located at 525 Chequessett Neck Road in Wellfleet, Massachusetts, United States. This cozy retreat offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to escape the hustle and bustle of everyday life. With a convenient location near the beach and other local attractions, Aunt Sukie Bed and Breakfast is the perfect place to relax and unwind during your stay in Wellfleet. Experience the comfort and hospitality of Aunt Sukie's home away from home.

Even'tide Resort & Cottages is a charming lodging establishment located in Wellfleet, Massachusetts. Situated at 650 U.S. 6, this resort offers cozy cottages and comfortable rooms for guests to enjoy a relaxing stay on Cape Cod. The resort is surrounded by beautiful scenery and is just a short drive away from the beach, making it the perfect destination for a seaside getaway. With friendly staff, clean accommodations, and a peaceful atmosphere, Even'tide Resort & Cottages is a great choice for those looking to unwind and rejuvenate in a tranquil setting.

Cooks By The Ocean is a charming lodging institution located at 420 Lecount Hollow Road in Wellfleet, Massachusetts. Nestled along the picturesque coastline of Cape Cod, this cozy retreat offers guests a peaceful and relaxing escape by the ocean. With comfortable accommodations and a warm, welcoming atmosphere, Cooks By The Ocean is the perfect destination for those looking to unwind and enjoy the beauty of the seaside. Whether you're seeking a romantic getaway or a family vacation, this charming inn is sure to make your stay unforgettable.