TOP 30 Best Luxury vacation getaway rentals in Dennis, Massachusetts

Dennis Seashores Cottages is a charming real estate and travel agency located at 20 Chase Avenue in Dennis, Massachusetts. Our agency specializes in providing cozy and comfortable cottages by the sea for rent or sale. With stunning ocean views and convenient access to the beach, our cottages are the perfect getaway for those looking to relax and unwind by the water. Whether you're looking for a weekend retreat or a long-term vacation rental, Dennis Seashores Cottages has the perfect seaside escape for you. Contact us today to book your stay at one of our beautiful cottages on the shores of Dennis.

Bluegreen Vacations The Soundings, Ascend Resort Collection is a charming lodging institution located at 79 Chase Avenue in Dennis, Massachusetts, United States. Situated right on the beautiful shores of Cape Cod, this resort offers guests a peaceful and picturesque getaway. The accommodations are spacious and comfortable, with modern amenities and stunning views of the ocean. Guests can relax by the outdoor pool, take a stroll along the beach, or explore the nearby attractions such as museums, shops, and restaurants. Whether you're looking for a romantic retreat or a fun family vacation, Bluegreen Vacations The Soundings is the perfect destination.

Nauset Rental is a real estate and travel agency located at 56 Main Street in Orleans, Massachusetts. Specializing in Lower and Mid Cape Rentals in towns such as Orleans, Chatham, Harwich, Brewster, and Dennis, Nauset Rental offers secure online payments, damage and travel insurance, and is locally owned and operated with proper licensing and insurance. Guests have raved about their experiences at Nauset Rental properties, praising the beautiful locations, amenities such as games and music systems, and the excellent customer service provided by owner Kent. With private beach access and stunning views, guests have enjoyed the peaceful and secluded atmosphere of the neighborhoods while still being close to activities and attractions.

My Cape Cod Vacation Home is a coastal retreat located in Dennis Port, Massachusetts, offering a peaceful getaway on beautiful Cape Cod. Our lodging establishment features 5 uniquely designed guest rooms, each providing a tranquil environment for a restful night's sleep. Situated within walking distance to the beach, guests can enjoy the sun, sand, and surf just moments away. Additionally, our property boasts a cozy fire pit for evening relaxation and central air conditioning for ultimate comfort. Whether you're looking for a relaxing beach vacation or a convenient home base for exploring all that Cape Cod has to offer, My Cape Cod Vacation Home is the perfect choice.

Nauset Rental is a real estate and travel agency located at 3 Main Street in Eastham, Massachusetts. Specializing in Lower and Mid Cape Rentals in towns such as Orleans, Chatham, Harwich, Brewster, and Dennis, Nauset Rental offers secure online payments, damage and travel insurance, and is locally owned and operated with proper licensing and insurance. Guests have raved about their experiences staying at Nauset Rental properties, praising the lovely houses and locations, short walks to beautiful beaches, and amenities such as games and music systems. The owner, Kent, has been described as a joy to work with, accommodating last-minute bookings and even welcoming guests with pets. The properties offer private beach access, stunning views, and a quiet, secluded neighborhood close to activities.

Seaside Summer Rentals is a premier real estate and travel agency located at 1370 Massachusetts 134 in Dennis, Massachusetts. We specialize in providing luxury vacation rentals along the picturesque seaside of Cape Cod. Our properties range from cozy beach cottages to spacious waterfront estates, ensuring that every guest can find their perfect summer retreat. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream getaway by the sea!

Near Beach Rentals is a cozy lodging option located at 183 Captain Chase Road in Dennis, Massachusetts. Just a stone's throw away from the beach, this institution offers comfortable accommodations for those looking to enjoy a relaxing getaway by the sea. Whether you're looking for a romantic escape or a fun-filled family vacation, Near Beach Rentals provides the perfect home base for your coastal adventures. With its convenient location and charming atmosphere, this institution is the ideal choice for travelers seeking a peaceful retreat near the shore.

Sun Retreats Dennis Port is a charming lodging facility located at 184 Old Wharf Road in Dennis, Massachusetts. Situated in the beautiful United States, this institution offers a peaceful retreat for visitors looking to relax and unwind. With comfortable accommodations and a serene atmosphere, guests can enjoy a truly rejuvenating experience. In addition to traditional lodging options, Sun Retreats Dennis Port also offers RV park facilities for those traveling by recreational vehicle. Whether you're looking for a weekend getaway or a longer stay, Sun Retreats Dennis Port is the perfect destination for a memorable vacation.

Seascape Vacation Rental Cape Cod is a premier real estate and travel agency located at 253 Old Wharf Road in Dennis, Massachusetts. Offering a wide selection of vacation rental properties in the picturesque Cape Cod area, Seascape is dedicated to providing guests with a memorable and relaxing getaway experience. With stunning ocean views, luxurious accommodations, and top-notch customer service, Seascape Vacation Rental Cape Cod is the perfect choice for those looking to escape the hustle and bustle of everyday life and immerse themselves in the natural beauty of the Cape Cod region. Book your dream vacation with Seascape today and create lasting memories that will last a lifetime.

Holiday Vacation Condominiums is located at 488 Main Street in Yarmouth, Massachusetts, United States. Situated in West Yarmouth, HVC is centrally located to all the attractions that Cape Cod has to offer. Just minutes away from the historical towns of Dennis, Harwich, Hyannis, and Yarmouth, as well as the beautiful beach fronts, a stay at HVC guarantees that you will have the best opportunity to explore and enjoy all the beauty and entertainment that Cape Cod has to offer. Our One-Bedroom unit is perfect for those seeking a comfortable stay, while our charming Studio Unit is ideal for your next vacation. Click the link below to learn more about the nearby attractions and beaches for your next stay at The Holiday Vacation Condominiums.

Cape Cod Rentals is a premier vacation rental agency located at 9 Dexter Snow Avenue in Dennis, Massachusetts. Offering a wide selection of beautiful and well-maintained vacation homes and cottages throughout the Cape Cod area, Cape Cod Rentals is dedicated to providing guests with a comfortable and memorable stay. Whether you're looking for a beachfront property or a cozy retreat in the woods, Cape Cod Rentals has the perfect accommodation for your next getaway. With excellent customer service and a convenient location, Cape Cod Rentals is the ideal choice for your Cape Cod vacation.

Cape House Rental is a reputable real estate agency located at 42 Seaside Avenue in Dennis, Massachusetts, United States. Specializing in rental properties in the beautiful Cape Cod area, our agency offers a wide selection of vacation homes, cottages, and beachfront properties for short-term and long-term stays. With personalized service and a team of experienced agents, Cape House Rental is dedicated to helping clients find the perfect home away from home for their next getaway. Experience the charm and beauty of Cape Cod with Cape House Rental.

Mayflower Beach is a stunning seaside retreat located at 14 Horsefoot Path in Dennis, Massachusetts. This picturesque beach offers pristine white sands, crystal clear waters, and breathtaking views of Cape Cod Bay. Visitors can relax on the shore, go for a swim, or simply soak up the sun while enjoying the peaceful atmosphere of this beautiful beach. With convenient amenities and a tranquil setting, Mayflower Beach is the perfect destination for a day of relaxation and fun in the sun.

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.

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.

Oceanside Condos is a stunning waterfront property located at 154 Old Wharf Road in Dennis, Massachusetts, United States. Offering luxurious accommodations with breathtaking views of the ocean, this institution provides a relaxing and tranquil retreat for guests looking to escape the hustle and bustle of everyday life. The condos are beautifully appointed and equipped with modern amenities to ensure a comfortable stay. With easy access to the beach and nearby attractions, Oceanside Condos is the perfect destination for a memorable vacation on Cape Cod.

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.

Three Seasons Resort is a charming lodging destination located at 421 Old Wharf Road in Dennis, Massachusetts. Situated in the heart of Cape Cod, this resort offers guests a peaceful and relaxing escape surrounded by beautiful landscapes and just steps away from the beach. With comfortable accommodations, friendly staff, and a range of amenities including a pool, tennis courts, and bike rentals, Three Seasons Resort is the perfect choice for a memorable vacation on the East Coast. Whether you're looking to unwind by the ocean or explore the local attractions, this quaint resort is the ideal home away from home.

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.

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.

Heritage Sands is a charming lodging institution located at 61 Old Wharf Road in Dennis, Massachusetts, United States. Nestled along the picturesque coastline of Cape Cod, this seaside retreat offers guests a unique and memorable vacation experience. With cozy cottages, stunning ocean views, and easy access to the beach, Heritage Sands is the perfect destination for those seeking relaxation and rejuvenation. Whether you're looking to unwind by the water, explore the local shops and restaurants, or simply soak up the sun on the sandy shores, Heritage Sands has something for everyone. Come discover the beauty and tranquility of this idyllic retreat on the shores of Cape Cod.

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.

The Beach House Inn is a charming lodging establishment located at 61 Uncle Stephens Road in Dennis, Massachusetts. Situated just steps away from the beautiful beaches of Cape Cod, this cozy inn offers guests a peaceful and relaxing retreat. The rooms are tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning ocean views, take a leisurely stroll along the shoreline, or simply relax on the inn's sun deck. With its convenient location and warm hospitality, the Beach House Inn is the perfect choice for a beach getaway in the United States.

Port-Harborside Condominium is a charming waterfront property located at 190 Upper County Road in Dennis, Massachusetts. This idyllic retreat offers stunning views of the harbor and easy access to the beach, making it the perfect destination for a relaxing getaway. The condominium features spacious and well-appointed units, each with modern amenities and a cozy atmosphere. Guests can enjoy a range of on-site facilities, including a swimming pool, fitness center, and barbecue area. With its convenient location and picturesque surroundings, Port-Harborside Condominium is the ideal choice for those seeking a peaceful escape by the sea.

Located at 60 Ocean Drive in Dennis, Massachusetts, Uppvall Cottages is a real estate and travel agency that offers the perfect homeport for your Cape Cod vacation. Whether you're looking to relax on the beach, go windsurfing, or explore the many points of interest on the Cape, we have something for everyone. With 115 sandy beaches to choose from, including the Cape Cod National Seashore, there's no shortage of fun in the sun. Choose to vacation with us in the bustling months of July and August, or opt for a more peaceful experience at the beginning or end of the summer season. Create wonderful vacation memories with us at Uppvall Cottages.

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.

Glendon Beach Cottages is a charming lodging establishment located at 91 Glendon Road in Dennis, Massachusetts, United States. These cozy cottages offer a peaceful retreat just steps away from the beautiful Glendon Beach. Each cottage is tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning ocean views, relax on the private deck, or take a leisurely stroll along the sandy shores. Whether you're looking for a romantic getaway or a fun family vacation, Glendon Beach Cottages is the perfect choice for your next seaside escape.

Oceanside Motel is a charming lodging establishment located at 329 Main Street in Dennis, Massachusetts, United States. Situated just steps away from the beautiful shoreline, this cozy motel offers comfortable accommodations and a relaxing atmosphere for guests looking to unwind and enjoy a seaside getaway. With its convenient location and friendly staff, Oceanside Motel is the perfect choice for travelers seeking a peaceful and picturesque retreat by the ocean.

The Cape Summer House is a premier real estate and travel agency located at 46 Glendon Road in Dennis, Massachusetts. Specializing in luxury vacation rentals and properties for sale on Cape Cod, our team of experienced agents are dedicated to helping clients find their perfect summer retreat. Whether you're looking to rent a beachfront cottage for a week or purchase a stunning waterfront home, The Cape Summer House is your one-stop destination for all things Cape Cod. Contact us today to start planning your dream summer getaway!

The Sayre House is a unique institution located at 20 Uncle Johns Road in Dennis, Massachusetts, United States. As a real estate agency, we specialize in helping clients find their dream homes in this beautiful coastal town. Additionally, as a travel agency, we offer personalized vacation planning services to ensure a memorable and stress-free getaway. Our team of experienced professionals is dedicated to providing top-notch service and guidance to meet all of our clients' needs. Visit The Sayre House today and let us help you find your perfect home or plan your next unforgettable vacation.