TOP 10 Romantic getaway cottages in Massachusetts

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The Berkshires Cottage is a charming real estate and travel agency located at 87 Blunt Road in Great Barrington, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Berkshires region, our agency offers a wide range of cozy cottages, luxurious estates, and scenic properties for visitors and residents alike. Whether you're looking for a weekend getaway or a permanent vacation home, our experienced team is dedicated to helping you find the perfect place to call your own in this beautiful corner of the United States. Visit us at The Berkshires Cottage and let us help you make your dream of living in the Berkshires a reality.

Grieshaber's Getaway is a premier travel agency located at 60 Sutton Place in East Longmeadow, Massachusetts. We specialize in creating unforgettable travel experiences for our clients, offering a wide range of services including booking flights, accommodations, and activities. Our team of experienced travel experts is dedicated to providing personalized service and expert advice to help you plan the perfect getaway. Whether you're looking for a relaxing beach vacation, a thrilling adventure, or a romantic escape, Grieshaber's Getaway has you covered. Contact us today to start planning your dream vacation!

Located at 135 South Shore Drive in Yarmouth, Massachusetts, Seaside Cottages offers a relaxing getaway on the oceanfront with a private beach overlooking Nantucket Sound. Our five-acre cottage colony is the perfect destination for couples and families looking to unwind and enjoy the beauty of Cape Cod. When you book directly with us, you won't have to worry about any additional booking or cleaning fees. Take advantage of our May special - stay 2 nights and get the 3rd night free! Or plan your fall getaway with our fall special - stay 2 nights and get the 3rd night 50% off. Just make sure to book online and note that blackout dates apply.

The Cottage B and B is a charming lodging establishment located at 14 Prospect Hill Road in the picturesque town of Stockbridge, Massachusetts. This historic bed and breakfast offers cozy accommodations in a beautifully restored cottage, providing guests with a peaceful and relaxing retreat. In addition to its comfortable rooms, The Cottage B and B also features a small museum showcasing local artifacts and history, adding a unique touch to the overall guest experience. Whether you are looking for a romantic getaway or a cultural escape, The Cottage B and B is the perfect destination for your next visit to Stockbridge.

The Lake House Guest Cottages of the Berkshires is a charming retreat nestled on the shores of Pontoosuc Lake in Lanesborough, Massachusetts. This picturesque institution offers cozy and beautifully appointed cottages for overnight stays, providing guests with a peaceful and serene atmosphere to relax and unwind. The on-site restaurant serves delicious meals made with locally sourced ingredients, offering a taste of the region's culinary delights. Whether you're looking for a romantic getaway, a family vacation, or a solo escape, The Lake House Guest Cottages of the Berkshires is the perfect destination for a memorable and rejuvenating experience.

Cavalier Cottage Bed & Breakfast is a charming lodging establishment located at 236 East Oxbow Road in the picturesque town of Charlemont, Massachusetts. This cozy retreat offers guests a peaceful and comfortable stay in a beautiful countryside setting. The cottage-style accommodations are tastefully decorated and feature modern amenities to ensure a relaxing experience. Guests can enjoy a delicious homemade breakfast each morning and take advantage of the convenient location near outdoor recreational activities such as hiking, skiing, and river rafting. Whether you are looking for a romantic getaway or a relaxing escape, Cavalier Cottage Bed & Breakfast is the perfect destination for your next vacation.

Menemsha Inn & Cottages is a charming and peaceful retreat located at 457 North Road in the picturesque town of Chilmark, Massachusetts. This unique institution offers a combination of health, lodging, and park amenities, providing guests with a truly rejuvenating experience. The inn features cozy cottages nestled among lush gardens and scenic surroundings, offering a tranquil escape from the hustle and bustle of everyday life. Guests can enjoy comfortable accommodations, delicious meals, and a variety of wellness activities such as yoga classes, spa treatments, and nature walks.

A Lady Winnette Cottage is a charming lodging establishment located at 3 Corinthian Lane in the picturesque town of Marblehead, Massachusetts, United States. This cozy cottage offers a peaceful retreat for guests looking to relax and unwind in a serene coastal setting. With comfortable accommodations and a warm, welcoming atmosphere, A Lady Winnette Cottage is the perfect choice for a romantic getaway or a peaceful weekend escape. Experience the beauty and tranquility of Marblehead at this lovely institution.

Inkwell Beach Cottage is a charming lodging located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Nestled in a picturesque seaside town, this cozy cottage offers a relaxing and comfortable retreat for guests looking to unwind and enjoy the beauty of Martha's Vineyard. Just steps away from the sandy shores of Inkwell Beach, guests can enjoy stunning ocean views and easy access to swimming, sunbathing, and beachcombing. The cottage features well-appointed rooms, a fully equipped kitchen, and a spacious living area, making it the perfect home-away-from-home for a seaside getaway. Whether you're looking for a romantic escape or a fun-filled family vacation, Inkwell Beach Cottage provides a peaceful and idyllic setting for your next trip to the Cape Cod area.

Lighthouse Lane Cottages is a charming lodging option located at 5 Lighthouse Lane in Rockport, Massachusetts, United States. This institution offers cozy and well-appointed cottages for rent, making it the perfect accommodation choice for travelers looking for a peaceful and relaxing getaway. As a real estate agency, Lighthouse Lane Cottages also helps clients find their dream vacation home or investment property in the scenic coastal town of Rockport. Additionally, as a travel agency, they can assist guests in planning their itinerary and exploring the best attractions and activities in the area. Whether you are looking for a weekend escape or a long-term rental, Lighthouse Lane Cottages is your go-to destination for a memorable and enjoyable stay in Rockport.

Whaleback Hill Cottages is a charming lodging institution located in the picturesque town of Sandwich, Massachusetts. Nestled on a scenic hilltop overlooking the historic Route 6A, this cozy retreat offers a peaceful and relaxing getaway for guests looking to unwind and rejuvenate. The cottages are beautifully appointed with modern amenities and rustic charm, providing a comfortable and inviting atmosphere for visitors. Whether you're seeking a romantic escape, a family vacation, or a solo retreat, Whaleback Hill Cottages is the perfect destination for your next stay in Cape Cod.

Dunroamin Trailer Park & Cottages is a charming lodging facility located at 5 John Ewer Road in Sandwich, Massachusetts. Offering a quaint and cozy atmosphere, this institution provides a range of accommodations including trailers and cottages for guests looking to enjoy a relaxing getaway. Situated in a picturesque setting, Dunroamin Trailer Park & Cottages is the perfect destination for RV enthusiasts and vacationers seeking a peaceful retreat in the United States. With its convenient location and comfortable amenities, guests are sure to have a memorable stay at this lovely establishment.

Truro Beach Cottages, located at 640 Shore Road in Truro, Massachusetts, offers a perfect escape for those looking to relax and unwind by the beach. Guests have raved about the cleanliness of the cottages, especially during these Covid times, and many have returned for another stay. The property is pet-friendly, making it a great option for those looking to bring their furry friends along for a vacation. The cottages provide a comfortable and stylish stay, with new flooring, kitchens, bathrooms, and mini-split AC systems. Guests can relax on the deck chairs and enjoy the stunning views of the dunes and the Atlantic Ocean. A short drive to downtown Truro and Provincetown offers a variety of activities, including art galleries, watersports, dining, and shopping.

East Harbour Motel & Cottages is a charming lodging establishment situated at 618 Shore Road in Truro, Massachusetts, United States. Nestled in a picturesque location, this institution offers cozy accommodations in the form of comfortable motel rooms and quaint cottages. Guests can enjoy the serene surroundings and easy access to the nearby beaches and attractions. Whether you are looking for a relaxing getaway or a fun-filled vacation, East Harbour Motel & Cottages is the perfect place to stay. Experience warm hospitality and a memorable stay at this lovely institution.

The Cottages at Nantucket Boat Basin is a charming lodging option located at 24 Old South Wharf in Nantucket, Massachusetts. This unique institution offers cozy cottages with stunning views of the marina, perfect for a relaxing getaway. As a real estate agency, they also offer opportunities to invest in waterfront properties in this picturesque location. Additionally, as a travel agency, they can help plan your dream vacation to Nantucket, ensuring a memorable experience. Whether you're looking for a weekend retreat or a long-term investment, The Cottages at Nantucket Boat Basin has everything you need for a perfect stay in this beautiful coastal town.

A Cape Shore Lodge & Cottages is a charming lodging establishment located at 6 Shore Road in Truro, Massachusetts, United States. Nestled along the picturesque Cape Cod shoreline, this cozy retreat offers comfortable accommodations in the form of both lodge rooms and cottages. Guests can enjoy stunning views of the ocean, relax on the sandy beaches, and explore the nearby attractions such as Cape Cod National Seashore and Provincetown. Whether you're looking for a romantic getaway or a family vacation, A Cape Shore Lodge & Cottages provides the perfect setting for a memorable stay on the Cape.

equipped for cooking meals and the sound of the waves lulls you to sleep at night. Highly recommend for a peaceful and relaxing getaway.

Mermaid Cottage is a charming lodging establishment located at 49 Cliff Street in Dennis, Massachusetts, United States. This cozy cottage offers a unique and relaxing getaway for guests looking to escape the hustle and bustle of everyday life. Decorated in a nautical theme, Mermaid Cottage provides a comfortable and inviting atmosphere for visitors to unwind and recharge. With its close proximity to the beach and local attractions, guests can enjoy a peaceful retreat while still being conveniently located near the heart of Dennis. Whether you're looking for a romantic weekend getaway or a family vacation, Mermaid Cottage is the perfect destination for a memorable stay by the sea.

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 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.

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.

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.

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.

Wheel In Cottages is a charming lodging establishment located in Eastham, Massachusetts, United States. As a real estate agency and travel agency, we offer cozy and comfortable cottages for your vacation getaway. Our cottages are equipped with all the amenities you need for a relaxing stay, including fully equipped kitchens, private bathrooms, and outdoor seating areas. Whether you're looking for a romantic retreat or a family vacation, Wheel In Cottages has the perfect accommodation for you. Book your stay with us today and experience the beauty of Cape Cod in style and comfort.

Bayview Cottages is a charming accommodation located at 658 Shore Road in the picturesque town of Provincetown, Massachusetts. Surrounded by stunning views of the bay, this cozy retreat offers a peaceful and relaxing atmosphere for guests to unwind and enjoy a memorable stay. The cottages are tastefully decorated and equipped with modern amenities to ensure a comfortable experience. Whether you are looking for a romantic getaway or a family vacation, Bayview Cottages is the perfect choice for your next trip to Cape Cod.

Michael's Cottages in Brewster is a charming accommodation located at 618 Main Street in the picturesque town of Brewster, Massachusetts. The cottages offer a cozy and comfortable stay for guests looking to experience the beauty of Cape Cod. Each cottage is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. The location is perfect for exploring the nearby beaches, shops, and restaurants. Whether you are looking for a romantic getaway or a family vacation, Michael's Cottages is the perfect choice for a memorable stay in Brewster.

Gull Cottage Bed & Breakfast is a charming lodging establishment located at 50 Steele Road in Wellfleet, Massachusetts. Nestled in a picturesque coastal town, this cozy B&B offers a relaxing getaway for visitors looking to unwind and enjoy the beauty of Cape Cod. With comfortable accommodations, delicious homemade breakfasts, and personalized hospitality, Gull Cottage is the perfect home away from home for travelers seeking a peaceful retreat by the sea. Experience the warmth and charm of this quaint bed and breakfast during your next visit to Wellfleet.

Ridgewood Motel & Cottages is a charming lodging establishment located at 10 Quanset Road in Orleans, Massachusetts, United States. Nestled in a serene and picturesque setting, this institution offers cozy accommodations in the form of both motel rooms and cottages. Guests can enjoy a peaceful stay surrounded by lush greenery and a tranquil atmosphere. The property is conveniently located near popular attractions, restaurants, and shops, making it an ideal choice for travelers looking to explore the beautiful Cape Cod area. Whether you are seeking a relaxing getaway or an adventurous vacation, Ridgewood Motel & Cottages provides a comfortable and inviting retreat for all types of guests.