TOP 10 Vacation cottage rentals in Massachusetts

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Pine Lake RV Resort & Cottages is a charming lodging destination located at 30 River Road in Sturbridge, Massachusetts. This beautiful resort offers a peaceful and scenic retreat for those looking to relax and unwind in the heart of nature. Guests can enjoy spacious RV sites with full hookups, as well as cozy cottages for a more traditional stay. The resort features a range of amenities including a swimming pool, playground, and recreational activities such as fishing and hiking. Whether you're looking for a weekend getaway or a longer vacation, Pine Lake RV Resort & Cottages is the perfect choice for your next adventure in Massachusetts.

Welcome to Berkshire Rental Properties, located at 29 Benton Avenue in Great Barrington, Massachusetts. Whether you're in search of a quaint cottage or a luxurious multifamily estate, Berkshire Rental Properties offers a wide range of options to suit your needs. Our listings are carefully selected for their desirability, location, and top-notch amenities, providing a step above the typical rental offerings. At Berkshire Rental Properties, we understand the allure of the Berkshires and aim to provide a seamless getaway experience for our guests. Whether you're seeking outdoor adventures, cultural experiences, or simply a relaxing retreat, our properties serve as the perfect gateway to all that the Berkshires have to offer.

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.

Cape Cod Vacation Rentals is a reputable real estate and travel agency located at 33 Bradford Street in Concord, Massachusetts. Specializing in providing high-quality vacation rental properties in the picturesque Cape Cod area, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're looking for a cozy beachfront cottage or a spacious luxury villa, our team of experienced agents is dedicated to helping you find the perfect vacation rental for your next getaway. With personalized service and attention to detail, Cape Cod Vacation Rentals is your go-to destination for a memorable and relaxing vacation experience on the beautiful shores of Cape Cod.

Del Mar Vacations is a well-established real estate and travel agency located in Orleans, Massachusetts. Specializing in vacation rentals and property management, our dedicated team is committed to providing top-notch service to clients looking to explore the beautiful Cape Cod area. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront home, Del Mar Vacations has a wide range of properties to suit every taste and budget. With our expert knowledge of the area and personalized approach, we strive to make your vacation experience unforgettable. Visit us at 24 South Orleans Road to start planning your dream getaway today.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires is a charming lodging destination nestled in the picturesque town of Lee, Massachusetts. Surrounded by the stunning beauty of the Berkshires, this resort offers a perfect retreat for families and couples looking to relax and unwind in a peaceful setting. The resort features spacious accommodations, including comfortable rooms and suites, all equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a range of on-site facilities, including indoor and outdoor pools, a fitness center, tennis courts, and a game room. There are also organized activities and events for guests of all ages to enjoy.

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.

Nantucket Rentals is a premier real estate and travel agency located at 53 Main Street in Nantucket, Massachusetts. We specialize in providing luxurious vacation rentals on the picturesque island of Nantucket. Our team of experienced agents will help you find the perfect rental property for your next getaway, whether you're looking for a cozy cottage by the beach or a spacious waterfront estate. With our local expertise and personalized service, we ensure that your Nantucket vacation is unforgettable. Contact us today to start planning your dream vacation on this charming island.

Martha's Vineyard Rentals is a reputable real estate and travel agency located at 13 Beach Street Extension in Tisbury, Massachusetts. Specializing in vacation rentals on the picturesque Martha's Vineyard island, this agency offers a wide range of properties to suit every traveler's needs. Whether you're looking for a cozy cottage by the beach or a luxurious waterfront estate, Martha's Vineyard Rentals has something for everyone. With personalized service and attention to detail, they strive to make your vacation experience unforgettable. Book your dream getaway with Martha's Vineyard Rentals today and start planning your perfect island escape.

The Salty Cottage is a charming real estate and travel agency located at 27 Locust Road in Eastham, Massachusetts. This cozy cottage is perfect for small families or two couples looking for a quiet retreat close to all the attractions Cape Cod has to offer. Situated in the heart of Eastham's Historic Town Center, it is just steps away from Salt Pond and the National Seashore Visitor Center, as well as a short bike ride to the Cape Cod Rail Trail. The cottage features two bedrooms with high-quality queen-size mattresses, pillows, and linens, along with a pull-out couch for larger groups. The bathroom includes a washer and dryer for added convenience. Guests can enjoy the modern decorations and finishes inside, or relax outside on the deck overlooking a natural wooded area, complete with outdoor shower and dining space for four.

Waterfront Rentals is a premier real estate and travel agency located at 411 Massachusetts 28 in Yarmouth, Massachusetts. Specializing in luxurious waterfront properties, our agency offers a wide range of rental options for those looking to enjoy the beauty of Cape Cod's stunning coastlines. Whether you're seeking a peaceful retreat or a fun-filled vacation, our experienced team is dedicated to helping you find the perfect rental for your needs. With top-notch customer service and a diverse selection of properties, Waterfront Rentals is your go-to destination for an unforgettable stay on the shores of Massachusetts.

Holiday Inn Club Vacations Oak n’ Spruce Resort - Tour Reception is a welcoming lodging institution located in Lee, Massachusetts, United States. Situated at 165 Meadow Street, this resort offers a relaxing and comfortable environment for guests to enjoy during their vacation. The tour reception area provides guests with information about the resort's amenities and activities, ensuring a memorable stay for all visitors. With its convenient location and friendly staff, Holiday Inn Club Vacations Oak n’ Spruce Resort - Tour Reception is the perfect choice for those seeking a peaceful getaway in the beautiful Berkshires region.

Vacation Village in the Berkshires is a charming lodging institution located at 276 Brodie Mountain Road in Hancock, Massachusetts, United States. Nestled in the picturesque Berkshires region, this resort offers cozy accommodations and top-notch amenities for a relaxing and enjoyable vacation experience. Guests can unwind in spacious suites equipped with modern comforts, take a dip in the indoor or outdoor pools, or explore the nearby attractions such as ski slopes, hiking trails, and cultural venues. Whether you're seeking a romantic getaway or a fun family vacation, Vacation Village in the Berkshires is the perfect destination for your next trip.

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.

Marriott Vacation Club Pulse at Custom House, Boston is a luxurious lodging institution located at 3 McKinley Square, in the heart of Boston, Massachusetts, United States. This historic building offers stunning views of the city skyline and waterfront, along with modern amenities and comfortable accommodations. Guests can enjoy easy access to popular attractions, shopping, and dining options in the bustling city center. Whether you are visiting for business or leisure, Marriott Vacation Club Pulse at Custom House provides a convenient and elegant stay in one of America's most vibrant cities.

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.

Gloucester House Rental - Belle View is a charming lodging establishment located at 57 Grapevine Road in Gloucester, Massachusetts, United States. As a real estate and travel agency, we specialize in providing luxurious house rentals with breathtaking views of the surrounding area. Our properties are meticulously maintained and offer all the amenities needed for a comfortable and relaxing stay. Whether you are looking for a weekend getaway or a longer vacation, Gloucester House Rental - Belle View is the perfect choice for your next trip to Gloucester.

Sea Breeze Inn beach rentals is a charming lodging located at 270 Ocean Avenue in Barnstable, Massachusetts, United States. Situated near the beautiful coastline, this institution offers cozy and comfortable accommodations for guests looking to enjoy a relaxing beach getaway. With a serene atmosphere and stunning ocean views, Sea Breeze Inn is the perfect destination for those seeking a peaceful retreat by the sea. Whether you're looking to unwind on the beach, explore the nearby attractions, or simply relax in the comfort of your room, Sea Breeze Inn beach rentals provides a warm and welcoming stay for all visitors.

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.

Lis Sur Mer Artists Cottages, located on Knowles Heights Road in Truro, Massachusetts, is a magical and unique lodging experience. Inspired by the dream of living alone by the sea, the cottages are designed to provide a true Old Cape Cod experience. Privacy is key at Lis Sur Mer, with dunes sculpted and lush plantings creating a sense of seclusion between the three cottages. Many guests feel like they have been transported to another country when they first arrive at Lis Sur Mer, and the eclectic, funky design of the cottages adds to the charm of this special place. Experience the beauty and tranquility of Lis Sur Mer for yourself and create your own dream by the sea."