The 30 Best Vacation home rentals in Massachusetts

Holiday Apartments is a charming accommodation located at 37 River Street in West Springfield, Massachusetts. Our apartments offer a cozy and comfortable space for visitors looking for a home away from home during their holiday. With a convenient location near local attractions and amenities, Holiday Apartments is the perfect choice for travelers seeking a relaxing and enjoyable stay in the United States. Whether you are visiting for business or pleasure, our apartments provide all the comforts and conveniences you need for a memorable stay. Book your stay with us today and experience the warmth and hospitality of Holiday Apartments.

Staffordshire Country Estates is a prestigious institution located at 500 Stafford Street in Leicester, Massachusetts, United States. Nestled in a picturesque setting, this estate offers luxurious and elegant living spaces for those seeking a refined lifestyle. With beautifully landscaped grounds, top-notch amenities, and unparalleled service, Staffordshire Country Estates provides residents with a truly exceptional living experience. Whether you're looking for a peaceful retreat or a vibrant community, this institution has something for everyone. Experience the epitome of luxury living at Staffordshire Country Estates.

Castle Cove Villa is a luxurious real estate and travel agency located at 202 Killdeer Road in Webster, Massachusetts. Our stunning villa offers a unique and unforgettable experience for those seeking a peaceful and relaxing getaway. Situated in a picturesque location, our villa boasts breathtaking views of the surrounding landscape and a tranquil atmosphere that is perfect for unwinding and rejuvenating. Whether you are looking to purchase a dream vacation home or book a memorable holiday rental, Castle Cove Villa is here to make your travel dreams a reality. Contact us today to start planning your next unforgettable escape.

Summer House is a charming institution nestled in the heart of Southwick, Massachusetts. Located at 552 College Highway, it is a delightful combination of a food establishment, restaurant, and store all rolled into one. With a warm and inviting atmosphere, Summer House offers a diverse menu of delicious dishes, as well as a selection of unique and locally sourced products for purchase. Whether you're looking for a tasty meal, a relaxing dining experience, or a one-of-a-kind shopping experience, Summer House has something for everyone. Come and visit us today and discover the joys of summer all year round.

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.

AAA Westfield is a trusted insurance and travel agency located at 16 North Elm Street in Westfield, Massachusetts, United States. With a commitment to providing exceptional service and comprehensive coverage options, AAA Westfield is dedicated to meeting the needs of its clients. Whether you are looking for insurance for your home, car, or business, or planning your next vacation, the experienced team at AAA Westfield is here to help. Visit us today to learn more about how we can assist you with all of your insurance and travel needs.

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!

AAA Springfield is a trusted insurance and travel agency located at 1891 Wilbraham Road in Springfield, Massachusetts. Our experienced agents are dedicated to providing top-notch service and personalized solutions for all your insurance and travel needs. Whether you're looking for auto, home, or life insurance coverage, or planning your next vacation, AAA Springfield is here to help. Visit us today to experience the peace of mind and convenience that comes with being a member of our reputable institution.

Proximo Travel is a premier real estate and travel agency located at 7 Midstate Drive in Auburn, Massachusetts, United States. With a dedicated team of professionals, Proximo Travel offers a wide range of services including buying and selling properties, vacation rentals, and booking travel accommodations. Whether you're looking for your dream home or planning your next adventure, Proximo Travel is here to make your experience seamless and stress-free. Contact us today to start your journey towards your next destination.

Welcome to A-House, the premier night club located at 6 Masonic Place in Provincetown, Massachusetts. A-House is known for its vibrant atmosphere, top-notch DJs, and unforgettable parties. Join us for a night of dancing, socializing, and creating memories that will last a lifetime. Whether you're a local or just visiting, A-House is the place to be for a night out on the town. Come experience the excitement and energy of A-House for yourself!

Pretty Picky Properties is a real estate and travel agency located at 2421 Main Street in Brewster, Massachusetts. Specializing in Cape Cod vacation rentals, this agency offers a wide range of properties to choose from for your next getaway. With a focus on quality and attention to detail, Pretty Picky Properties ensures that each rental meets the highest standards of comfort and convenience. Whether you're looking for a beachfront escape or a cozy cottage near hiking trails, Pretty Picky Properties has the perfect vacation rental for you. Guests rave about the beautiful homes, great locations, and superb amenities offered by this agency. The attentive owner and property management team are quick to address any issues that may arise, ensuring a stress-free stay for all guests.

Island Real Estate is a prestigious real estate agency located at 107 Beach Road in Tisbury, Massachusetts. Specializing in waterfront properties and luxury homes, Island Real Estate offers a unique opportunity to own a piece of paradise on Martha's Vineyard. With panoramic views and exclusive listings like the Harthaven Waterfront Compound, this agency is the go-to destination for those seeking a dream home or vacation property. Whether you are looking to buy, sell, or rent, Island Real Estate's team of experienced agents is dedicated to helping you find the perfect property to suit your needs. Contact us today to start your journey to owning a piece of the beautiful Martha's Vineyard coastline.

The Pioneer is a reputable real estate agency located at 1760 Revere Beach Parkway in Everett, Massachusetts. With a dedicated team of experienced agents, The Pioneer is committed to helping clients find their dream homes or investment properties in the Greater Boston area. Whether you are buying, selling, or renting, The Pioneer offers personalized service and expert guidance throughout the entire real estate process. Trust The Pioneer to be your partner in achieving your real estate goals.

RESIDE Inc. is a premier furniture and home goods store located at 266 Concord Avenue in Cambridge, Massachusetts. Our store offers a wide selection of high-quality furniture, decor, and accessories to help you create the perfect living space. Whether you're looking to furnish a new home or simply update your current decor, RESIDE Inc. has everything you need to make your house feel like a home. Our friendly and knowledgeable staff are here to assist you in finding the perfect pieces to suit your style and budget. Visit us today and discover why RESIDE Inc. is the go-to destination for all your home furnishing needs.

Carbuncle Beach House is a charming park located at 12 Carbuncle Drive in Oxford, Massachusetts, United States. This serene and picturesque institution offers a peaceful retreat for visitors looking to escape the hustle and bustle of everyday life. With its beautiful beachfront setting and lush green surroundings, Carbuncle Beach House is the perfect place to relax, unwind, and connect with nature. Whether you're looking to enjoy a leisurely stroll along the shoreline, have a picnic with loved ones, or simply soak up the sun, Carbuncle Beach House provides a tranquil and rejuvenating experience for all who visit.

Karens Cleaning Services is a professional cleaning company located at 177 East Main Street in West Brookfield, Massachusetts. We specialize in providing top-quality cleaning services for residential and commercial properties. Our team of experienced and dedicated cleaners are committed to delivering exceptional results every time. Whether you need a one-time deep clean or regular maintenance, we have the skills and expertise to meet your needs. Contact Karens Cleaning Services today for a spotless and sparkling clean space.

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.

Beach Realty is a premier real estate and travel agency located at 133 North Shore Boulevard in Sandwich, Massachusetts. Our experienced team of agents specializes in buying and selling beachfront properties, vacation rentals, and investment properties in the beautiful coastal town of Sandwich. Whether you are looking for a dream beach house or planning a relaxing getaway, Beach Realty is here to help you find the perfect property to suit your needs. Contact us today to start your beachfront living experience!

Located at 29 Main Street in Orleans, Massachusetts, WeNeedaVacation.com is a premier institution offering lodging, real estate, and travel services. Specializing in vacation rentals on Cape Cod, Martha's Vineyard, and Nantucket since 1997, we provide a wide range of options for travelers looking to explore the beautiful beaches, natural landscapes, and unique history of these iconic destinations. From historic Plymouth to the tip of Provincetown, the Cape offers an unparalleled combination of beauty and fun activities. Martha's Vineyard Island boasts six charming towns and 110 square miles of natural beauty, while Nantucket features a preserved main town surrounded by picturesque seaside communities. We offer flexible-length plans with no hidden fees or commissions, guaranteeing booking results and providing personalized services and resources for our members. As the go-to rental site for the Cape & Islands, WeNeedaVacation.com ensures a memorable and stress-free vacation experience. For added protection, travelers can also obtain instant travel insurance quotes through our website.

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.

The Captain's House Plymouth is a charming and historic institution located at 8 Brewster Street in Plymouth, Massachusetts. As a real estate agency, they specialize in helping clients find their dream homes in this picturesque coastal town. Additionally, as a travel agency, they offer personalized vacation planning services to help visitors make the most of their time in Plymouth. With a team of experienced professionals and a deep knowledge of the local area, The Captain's House Plymouth is your go-to destination for all things real estate and travel in Plymouth, Massachusetts.

Berkshire Hathaway HomeServices Barnbrook Realty is a prestigious real estate agency located in the charming town of Great Barrington, Massachusetts. Situated at 271 Main Street, this agency specializes in helping clients buy and sell residential properties in the picturesque Berkshire region. With a team of experienced and knowledgeable real estate professionals, Berkshire Hathaway HomeServices Barnbrook Realty provides top-notch service and guidance to clients looking to find their dream home or investment property. Whether you are a first-time homebuyer or a seasoned investor, this agency is dedicated to helping you navigate the real estate market with ease and confidence.

Kris Cook, Realtor with Real Broker MA LLC is a reputable real estate agency located at 147 Berkshire Drive in Westfield, Massachusetts, United States. With years of experience in the industry, Kris Cook provides top-notch service to clients looking to buy or sell property in the area. Whether you are a first-time homebuyer or a seasoned investor, Kris Cook will guide you through the process with professionalism and expertise. Contact Kris Cook, Realtor with Real Broker MA LLC today to make your real estate dreams a reality.

CP Property Group is a reputable real estate agency located at 672 Chestnut Street in Springfield, Massachusetts, United States. With a team of experienced and dedicated professionals, CP Property Group specializes in buying, selling, and renting residential and commercial properties in the local area. Whether you are looking for your dream home, a new office space, or an investment property, CP Property Group is committed to providing top-notch service and expertise to help you achieve your real estate goals. Contact us today to learn more about how we can assist you with all of your real estate needs.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Berkshire Mountain Lodge is a charming lodging institution located at 8 Dan Fox Drive in Pittsfield, Massachusetts. Situated in the beautiful Berkshires region, the lodge offers a perfect blend of cultural attractions, historical sites, and natural beauty. Guests can explore nearby attractions such as The Mount, the former estate of American author Edith Wharton, and Tanglewood, the summer home of the Boston Symphony Orchestra. Berkshire Mountain Lodge is a family-friendly vacation destination that offers a variety of amenities and activities for guests of all ages. The resort has received numerous awards, including the RCI Gold Crown Status, Tripadvisor's Travelers' Choice Award, and the Hotels.com Loved by Guests Award, all of which recognize the exceptional service and hospitality provided by the lodge.

Stay Berkshires is a charming lodging institution located at 1146 Cold Spring Road in the picturesque town of Williamstown, Massachusetts. Nestled in the heart of the Berkshires, our cozy accommodations offer a peaceful retreat for visitors looking to relax and unwind in a beautiful natural setting. Whether you're exploring the nearby cultural attractions or simply seeking a tranquil escape, Stay Berkshires provides a comfortable and inviting home away from home. Experience the warmth and hospitality of our friendly staff as you enjoy all that the Berkshires have to offer.

Rose and Goat Retreat is a charming and cozy real estate and travel agency located in the picturesque town of North Adams, Massachusetts. Situated at 25 Moores Road, this institution offers a unique blend of services that cater to both property buyers and travelers looking for a peaceful escape. Whether you are in search of a dream home nestled in the scenic beauty of North Adams or planning a relaxing getaway to rejuvenate your soul, Rose and Goat Retreat has got you covered. With a team of experienced professionals and a wide range of properties and travel packages to choose from, you can trust that your needs and preferences will be taken care of with utmost care and attention to detail.

Hawk Mountain Lodge is a charming lodging establishment located at 7 Main Street in the picturesque town of Charlemont, Massachusetts. Nestled in the heart of the United States, this cozy retreat offers a tranquil and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and friendly service, Hawk Mountain Lodge is the perfect home away from home for travelers exploring the beautiful New England region. Whether you're seeking adventure in the nearby mountains or simply looking to unwind and recharge, a stay at Hawk Mountain Lodge promises a memorable and rejuvenating experience.

Blue Heron Farm in Charlemont, Massachusetts is a charming lodging destination nestled on 250 acres of pristine countryside. This unique institution offers a tranquil retreat for visitors looking to escape the hustle and bustle of city life. The farm also serves as a real estate agency, helping clients find their dream homes in the picturesque New England landscape. Additionally, Blue Heron Farm operates as a travel agency, providing personalized itineraries for those looking to explore the beauty of western Massachusetts. Whether you're seeking a peaceful getaway or looking to invest in a piece of paradise, Blue Heron Farm is the perfect destination for all your lodging, real estate, and travel needs.