TOP 10 Vacation homes in Massachusetts

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.

Cape Cod Wishing Well is a charming lodging institution located in Harwich, Massachusetts. Situated at 212 Massachusetts 28, this cozy retreat offers a peaceful and serene atmosphere for guests looking to relax and unwind on Cape Cod. The well-appointed rooms are designed with comfort in mind, and the friendly staff is dedicated to ensuring a memorable stay for every guest. Whether you're seeking a romantic getaway or a family vacation, Cape Cod Wishing Well is the perfect destination for your next trip to the beautiful Cape Cod region.

The Rockport Lodge is a charming lodging establishment located at 55 South Street in the picturesque town of Rockport, Massachusetts, United States. Surrounded by natural beauty and just a short walk from the ocean, this cozy retreat offers comfortable accommodations and a warm, welcoming atmosphere. Guests can enjoy peaceful surroundings, friendly service, and easy access to all the attractions and activities that Rockport has to offer. Whether you're looking for a relaxing getaway or a convenient home base for exploring the area, The Rockport Lodge is the perfect choice for your next stay.

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.

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.

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.

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.

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.

Handkerchief Shoals Inn is a charming lodging establishment located at 888 Massachusetts 28 in Harwich, Massachusetts. This cozy inn offers a comfortable and inviting atmosphere for guests looking to relax and unwind on Cape Cod. With its convenient location near the beach and various attractions, Handkerchief Shoals Inn is the perfect choice for those seeking a peaceful retreat. The well-appointed rooms and friendly staff ensure a pleasant stay for all visitors. Whether you're in town for a weekend getaway or an extended vacation, this quaint inn provides a warm and welcoming home away from home.

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.

Captain Gosnold Village is a charming lodging institution located at 230 Gosnold Street in the picturesque town of Barnstable, Massachusetts, in the United States. The village offers cozy and comfortable accommodations for guests looking to enjoy a relaxing getaway on Cape Cod. Surrounded by lush gardens and just a short walk from the beach, Captain Gosnold Village provides a peaceful and serene atmosphere for visitors to unwind and recharge. With its convenient location and welcoming atmosphere, this institution is the perfect choice for those seeking a memorable stay on the beautiful Massachusetts coast.

Rodeway Inn Orleans - Cape Cod is a cozy and inviting lodging establishment located in the picturesque town of Orleans, Massachusetts, in the heart of Cape Cod. Situated at 48 Cranberry Highway, this charming inn offers comfortable accommodations and excellent amenities for guests looking to explore the beauty of the Cape Cod area. Whether you are visiting for a relaxing beach vacation, a romantic getaway, or a family trip, Rodeway Inn Orleans - Cape Cod provides a convenient and affordable option for your stay. Enjoy easy access to nearby attractions, shopping, dining, and outdoor activities, making it the perfect home base for your Cape Cod adventure. Experience warm hospitality and a welcoming atmosphere at Rodeway Inn Orleans - Cape Cod.

Linger Longer By the Sea Apartments is a lodging institution located at 261 Linnell Landing Road in Brewster, Massachusetts, United States. This establishment offers terrific value for guests, with private beach access on Cape Cod Bay. The apartments have been updated and reconfigured, featuring multiple baths and available for daily or weekly rentals. Guests have praised the accommodations and the helpfulness of the staff, particularly mentioning the beautiful sunsets and long sandy beach perfect for leisurely walks. The institution also offers guided beachside exploration tours at low tide in collaboration with the Cape Cod Museum of Natural History.

The Summer House Cottages is a charming seaside retreat located at 17 Ocean Avenue in Siasconset, Massachusetts. This institution offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway by the ocean. The cozy cottages provide a comfortable and intimate stay, while the on-site restaurant serves delicious meals made with fresh, local ingredients. Guests can enjoy stunning views of the ocean and easy access to the beach, creating a peaceful and rejuvenating atmosphere. Whether you're looking for a romantic escape or a family vacation, The Summer House Cottages is the ideal choice for a memorable stay on the beautiful island of Nantucket.

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.

The Pine Knot Motel is a charming lodging establishment located at 890 Massachusetts 28 in Yarmouth, Massachusetts, United States. This cozy motel offers comfortable and affordable accommodations for travelers looking to explore the beautiful Cape Cod area. With its convenient location and friendly staff, guests can enjoy a relaxing stay while taking in the sights and attractions of the region. Whether you're visiting for a weekend getaway or an extended vacation, the Pine Knot Motel is the perfect home away from home.

The Bass River Motel is a cozy lodging establishment located in Yarmouth, Massachusetts, along the scenic Massachusetts Route 28. Situated in the heart of Cape Cod, this charming motel offers comfortable accommodations for travelers looking to explore the area's beautiful beaches, historic sites, and quaint villages. The Bass River Motel provides guests with clean and well-appointed rooms, friendly service, and convenient access to nearby attractions. Whether you're visiting for a weekend getaway or an extended vacation, the Bass River Motel is the perfect home base for your Cape Cod adventure.

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.

The Wellfleet Motel is a charming lodging option located at 170 U.S. 6 in Wellfleet, Massachusetts, United States. Nestled in a picturesque setting, this cozy motel offers comfortable and affordable accommodations for visitors looking to explore the beauty of Cape Cod. With its convenient location near popular attractions such as beaches, hiking trails, and local eateries, the Wellfleet Motel is the perfect home base for a relaxing vacation. Whether you're seeking a weekend getaway or an extended stay, this welcoming institution is sure to make your stay a memorable one.

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.

Located just a quarter mile from the famous Nauset Beach in Orleans, Massachusetts, the Ship's Knees Inn is a charming and unique lodging option. Housed in a restored sea captain's home dating back to 1820, this inn offers 16 individually appointed guest rooms, 14 of which have private baths. Guests can enjoy daily continental breakfast, an outdoor swimming pool, WiFi, and in-room air conditioning. The innkeepers, Peter and Denise Butcher, are known for their warm hospitality, making guests feel right at home. The beautiful property features rolling green lawns, colorful gardens, and quiet spots to relax. With its close proximity to Nauset Beach, guests can easily spend their days lounging on the sand or exploring the nearby attractions on Cape Cod. Whether you choose to unwind by the fire pit in the evenings or take a dip in the in-ground pool, the Ship's Knees Inn offers a peaceful haven for a memorable beach vacation getaway.

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.

Surf Side Cottages is a charming lodging option located at 370 Wilson Avenue in Wellfleet, Massachusetts, United States. This institution offers cozy and comfortable cottages for guests looking to enjoy a relaxing beach vacation. As a real estate agency, Surf Side Cottages also provides opportunities for those interested in purchasing a vacation home in this picturesque coastal town. Additionally, as a travel agency, they can assist guests in planning their ideal getaway to Wellfleet, whether it be for a weekend retreat or an extended stay. Experience the beauty of Cape Cod at Surf Side Cottages.

Cove Woods Bed & Breakfast is a charming lodging establishment located at 295 Cove Road in Wellfleet, Massachusetts, United States. Nestled in a serene wooded setting, this cozy bed and breakfast offers a peaceful retreat for guests looking to relax and unwind. The comfortable accommodations and warm hospitality provided by the friendly staff ensure a memorable stay. Whether you're exploring the nearby beaches, hiking trails, or just enjoying the tranquility of the surroundings, Cove Woods Bed & Breakfast is the perfect home away from home for your getaway in Cape Cod.

The Colony of Wellfleet is a unique lodging institution located at 640 Chequessett Neck Road in Wellfleet, Massachusetts, United States. Originally designed and built in 1948 by architects Nathaniel Saltonstall and Oliver P. Morton, this institution was known as the Mayo Hill Colony Club, serving as a private club and art gallery for artists and patrons. In 1963, Loris and Eleanor Stefani acquired the cottages and transformed them into a hotel, adding their own creative touches and artwork to create The Colony as it is known today. Managed by their son Jeffrey and his wife Mihae since 2019, The Colony offers a truly special summer retreat in the Northeast. The Colony of Wellfleet features 10 Bauhaus-style cottages overlooking Wellfleet harbor and bay, each designed for elegant functionality and furnished with pieces by leading modernists. Guests can enjoy reserved beach space, golf, tennis, pickleball, sailing lessons, and more at the club. The cafe offers coffee, pastries, lunch, and drinks with stunning views. Flexible membership options are available for guests.

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.