TOP 30 Luxury vacation getaway rentals in Massachusetts

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Rosie's B's in Holland is a charming institution located at 70 Allen Hill Road in Holland, Massachusetts. Our cozy and inviting space offers a wide range of delicious baked goods, including cakes, cookies, and pastries. Whether you're looking for a sweet treat to enjoy with a cup of coffee or a custom cake for a special occasion, Rosie's B's has you covered. Our friendly staff is dedicated to providing top-notch service and ensuring that every customer leaves satisfied. Stop by Rosie's B's in Holland today to indulge in some of the best baked goods in the United States.

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.

Happy Place Berkshires is a charming clothing store located at 312 Main Street in Great Barrington, Massachusetts. Step into a world of colorful and stylish fashion where you can find the perfect outfit to express your unique personality. From trendy tops to cozy sweaters, our store offers a wide selection of clothing for men and women. Whether you're looking for a casual everyday look or a special outfit for a night out, Happy Place Berkshires has something for everyone. Come visit us and experience the joy of shopping in a welcoming and cozy environment.

Riverboat is a vibrant and lively institution located at 11 South End Bridge in Agawam, Massachusetts. This unique establishment offers a combination of a bar, food, and restaurant all in one. With its cozy atmosphere and picturesque views of the nearby river, Riverboat is the perfect spot to unwind and enjoy a delicious meal or drinks with friends and family. Whether you're looking for a casual night out or a special occasion, Riverboat has something for everyone. Come visit us and experience the charm of this hidden gem in Agawam.

The Carriage House is a prestigious university located in the charming town of Great Barrington, Massachusetts, United States. Situated in a historic building, the institution offers a unique and inspiring learning environment for students. With a focus on academic excellence and innovation, the Carriage House provides a wide range of programs and resources to help students succeed in their chosen fields. The university's beautiful campus and dedicated faculty make it a top choice for those seeking a quality education in a picturesque setting.

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!

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.

Wallis Cove Cabins is a charming lodging institution nestled on Island Road in Douglas, Massachusetts, United States. Surrounded by the tranquil beauty of nature, these cozy cabins offer a peaceful retreat for guests looking to escape the hustle and bustle of everyday life. Each cabin is thoughtfully designed and equipped with modern amenities to ensure a comfortable stay. Whether you're seeking a romantic getaway or a family vacation, Wallis Cove Cabins provides the perfect setting for a memorable experience. Explore the nearby hiking trails, relax by the lake, or simply unwind on your private deck and take in the picturesque views. Experience the tranquility and serenity of Wallis Cove Cabins for a truly unforgettable stay.

Located in the picturesque town of Pittsfield, Massachusetts, the Best Western Plus Berkshire Hills Inn & Suites offers comfortable and modern lodging for travelers looking to explore the beautiful Berkshires region. Situated at 1350 West Housatonic Street, this hotel provides guests with a convenient location near popular attractions such as Tanglewood, Hancock Shaker Village, and the Norman Rockwell Museum. The hotel features spacious rooms and suites equipped with amenities such as free Wi-Fi, flat-screen TVs, and mini fridges. Guests can also enjoy a complimentary hot breakfast, a fitness center, and an indoor pool. Whether visiting for business or leisure, the Best Western Plus Berkshire Hills Inn & Suites provides a welcoming and relaxing atmosphere for all guests.

Stonover Farm is a charming lodging institution located at 169 Under Mountain Road in Lenox, Massachusetts, United States. Surrounded by picturesque countryside, this tranquil farm offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The property features beautifully appointed rooms, a cozy fireplace, and stunning views of the rolling hills. Guests can enjoy a relaxing stay in this idyllic setting, with opportunities for hiking, biking, and exploring the nearby attractions. Whether you're seeking a romantic getaway or a peaceful weekend retreat, Stonover Farm provides a warm and welcoming atmosphere for a memorable stay.

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.

Canyon Ranch Lenox is a renowned institution located at 165 Kemble Street in Lenox, Massachusetts, United States. This institution offers a unique combination of health, lodging, and spa services for guests looking to improve their overall well-being. One of the special offers at Canyon Ranch Lenox is the Best Friends Bonus Offer, where guests can save on double occupancy and receive extra services. The institution also hosts events such as The Canyon Ranch Weight Loss Program, designed to help guests achieve long-term weight loss goals.

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.

Club Wyndham Bentley Brook is a premier lodging destination nestled in the picturesque town of Hancock, Massachusetts. As a part of the renowned Wyndham vacation ownership network, this institution offers luxurious accommodations, top-notch amenities, and exceptional service. Whether you're looking for a relaxing getaway or an adventurous vacation, Club Wyndham Bentley Brook has something for everyone. With its prime location near ski slopes, hiking trails, and other outdoor activities, guests can enjoy a truly unforgettable experience. Plan your next vacation with Club Wyndham Bentley Brook and create lasting memories in the beautiful Berkshires region of Massachusetts.

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.

Chambery Inn is a charming lodging and spa located at 199 Main Street in Lee, Massachusetts. This historic inn offers a tranquil and luxurious retreat for guests seeking a peaceful getaway in the heart of the Berkshires. The beautifully appointed rooms feature elegant decor and modern amenities, creating a cozy and inviting atmosphere for relaxation. Guests can indulge in rejuvenating spa treatments, unwind in the serene garden courtyard, or explore the nearby attractions and activities in the picturesque town of Lee. With its convenient location and exceptional service, Chambery Inn is the perfect destination for a memorable and rejuvenating stay.

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.

Netherwood is a charming lodging institution located at 253 Kemp Avenue in the picturesque town of North Adams, Massachusetts, United States. Nestled in a serene and peaceful setting, Netherwood offers comfortable accommodations and a warm hospitality experience for guests seeking a relaxing getaway. With its convenient location and cozy atmosphere, Netherwood is the perfect place to unwind and enjoy the beauty of the surrounding area. Whether you are visiting for business or pleasure, Netherwood welcomes you with open arms and promises a memorable stay.

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.

Melody's Place Lodging is a charming retreat nestled in the picturesque town of Charlemont, Massachusetts. Located at 193 Main Street, this cozy inn offers a peaceful escape for guests looking to relax and rejuvenate. The welcoming atmosphere and comfortable accommodations make it the perfect destination for a weekend getaway or a longer stay. In addition to cozy rooms, Melody's Place also features a spa where guests can indulge in a variety of relaxing treatments. Whether you're seeking a tranquil retreat or a romantic getaway, Melody's Place Lodging is the ideal destination for your next vacation.

Downton Valley is a charming lodging institution located at 1089 Westhampton Road in Northampton, Massachusetts, United States. Nestled in the picturesque Downton Valley, this institution offers guests a peaceful and serene retreat surrounded by nature. The cozy rooms are elegantly decorated and provide all the comforts of home. Guests can enjoy a delicious breakfast in the dining area or relax on the outdoor patio overlooking the beautiful valley. With its convenient location and warm hospitality, Downton Valley is the perfect destination for a relaxing getaway.

The Inn on Boltwood is a charming and elegant institution located in the heart of Amherst, Massachusetts. Situated at 30 Boltwood Avenue, this historic property offers luxurious accommodations, exquisite dining options, and top-notch service. Whether you are looking for a comfortable place to stay, a delicious meal, or a relaxing getaway, the Inn on Boltwood is the perfect choice. With its convenient location and upscale amenities, this institution is sure to exceed your expectations and provide you with a memorable experience.

The Suite at Liberty Woods is a cozy lodging option located at 111 Federal Street in Belchertown, Massachusetts. Situated in a peaceful and picturesque setting, this charming establishment offers guests a comfortable and relaxing stay. The spacious suites are tastefully decorated and equipped with modern amenities to ensure a pleasant experience. Whether you are visiting for business or leisure, The Suite at Liberty Woods provides a welcoming atmosphere and attentive service to make your stay memorable. Enjoy the tranquility of the countryside while still being conveniently located near local attractions and amenities. Book your stay today and experience the warmth and hospitality of this lovely establishment.

Maguire House Bed & Breakfast is a charming and cozy lodging establishment located at 30 Cobb Road in Ashburnham, Massachusetts, United States. Nestled in a picturesque setting, this bed and breakfast offers a warm and welcoming atmosphere for guests looking for a peaceful retreat. The historic house features comfortable rooms with modern amenities, delicious homemade breakfast served each morning, and friendly hospitality from the owners. Whether you are visiting for a romantic getaway, a family vacation, or a business trip, Maguire House Bed & Breakfast is the perfect place to relax and unwind in a beautiful New England setting.

The VERVE Boston Natick, Tapestry Collection by Hilton is a stylish and modern lodging destination located at 1360 Worcester Street in Natick, Massachusetts, United States. This hotel offers a unique and vibrant atmosphere, with contemporary design and upscale amenities. Guests can enjoy comfortable accommodations, delicious dining options, and convenient access to nearby attractions. Whether traveling for business or leisure, The VERVE Boston Natick provides a welcoming and luxurious experience for all visitors.

Chateau Merrimack Resort & Spa is a luxurious lodging and spa institution located at 160 Pawtucket Boulevard in Tyngsborough, Massachusetts, United States. Our rooms are designed to provide the perfect balance of comfort and luxury, with modern amenities and a warm ambiance to enhance your stay. Guests can indulge in the refreshed elegance of our pool and JuJu Spa, now open for an exquisite escape into serenity and tranquility. Whether you are looking for a relaxing getaway or a rejuvenating spa service, Chateau Merrimack offers an oasis of indulgence for all guests. Book your stay or spa service today and immerse yourself in luxury at Chateau Merrimack Resort & Spa.

Riverview Inn & Suites is a charming lodging establishment located at 1878 Wilbur Avenue in Somerset, Massachusetts, United States. Situated along the picturesque river, guests can enjoy stunning views and a peaceful atmosphere during their stay. The inn offers comfortable accommodations and modern amenities, making it the perfect choice for both leisure and business travelers. With friendly staff, convenient location, and affordable rates, Riverview Inn & Suites is the ideal destination for a relaxing getaway in Somerset.

Lakeside Inn is a charming lodging establishment located at 595 North Avenue in Wakefield, Massachusetts, United States. Situated by a picturesque lake, Lakeside Inn offers a peaceful retreat for guests looking to relax and unwind. The inn features cozy rooms, a welcoming atmosphere, and stunning views of the surrounding natural beauty. Whether you are visiting for a weekend getaway or a longer stay, Lakeside Inn provides a comfortable and serene setting for your stay in Wakefield.