TOP 30 Best Relaxing vacations in Massachusetts

Jiminy Peak Vacation Home Rentals is a real estate and travel agency located at 37 Corey Road in Hancock, Massachusetts, United States. We offer cozy vacation homes perfect for winter weekends, holiday periods, and spring, summer, and fall getaways. For winter weekends and holiday periods, we require a 7-day cancellation notice with a 10% cancellation fee of the total reservation. For midweek stays during non-holiday periods, we require a 48-hour cancellation notice with the same cancellation fee policy.

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.

Sagres Vacations is a premier travel agency located at 139 South Main Street in Fall River, Massachusetts. We specialize in creating unforgettable vacation experiences for our clients, offering a wide range of travel packages to destinations around the world. 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 cultural adventure, or a romantic escape, Sagres Vacations has the expertise to make your travel dreams a reality. Contact us today to start planning your next unforgettable vacation!

Bluegreen Vacations The Soundings, Ascend Resort Collection is a charming lodging institution located at 79 Chase Avenue in Dennis, Massachusetts, United States. Situated right on the beautiful shores of Cape Cod, this resort offers guests a peaceful and picturesque getaway. The accommodations are spacious and comfortable, with modern amenities and stunning views of the ocean. Guests can relax by the outdoor pool, take a stroll along the beach, or explore the nearby attractions such as museums, shops, and restaurants. Whether you're looking for a romantic retreat or a fun family vacation, Bluegreen Vacations The Soundings is the perfect destination.

Martha's Vineyard Vacation Rentals & Real Estate is a premier real estate and travel agency located at 107 Beach Road in Tisbury, Massachusetts, United States. Specializing in luxury vacation rentals and real estate properties on the beautiful Martha's Vineyard island, our dedicated team is committed to providing exceptional service and helping clients find their perfect getaway or dream home. Whether you are looking for a relaxing vacation rental or interested in investing in property on the island, Martha's Vineyard Vacation Rentals & Real Estate has the expertise and resources to make your experience unforgettable. Contact us today to start planning your Martha's Vineyard escape!

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.

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.

FearlessRose vacation rental is a cozy and welcoming lodging institution located on Appleton Street in Springfield, Massachusetts, United States. Our rental property offers a comfortable and stylish accommodation option for travelers looking to experience the charm of Springfield. With modern amenities, spacious rooms, and a convenient location, FearlessRose vacation rental is the perfect choice for a relaxing and enjoyable stay in the area. Whether you are visiting for business or pleasure, our institution provides a peaceful retreat where you can unwind and recharge during your trip. Book your stay with us today and experience the comfort and convenience of FearlessRose vacation rental.

My Cape Cod Vacation Home is a coastal retreat located in Dennis Port, Massachusetts, offering a peaceful getaway on beautiful Cape Cod. Our lodging establishment features 5 uniquely designed guest rooms, each providing a tranquil environment for a restful night's sleep. Situated within walking distance to the beach, guests can enjoy the sun, sand, and surf just moments away. Additionally, our property boasts a cozy fire pit for evening relaxation and central air conditioning for ultimate comfort. Whether you're looking for a relaxing beach vacation or a convenient home base for exploring all that Cape Cod has to offer, My Cape Cod Vacation Home is the perfect choice.

High Pocket Vacation Rental is a charming lodging located at 38 Adams Place in the picturesque town of Colrain, Massachusetts, United States. Nestled in a serene and peaceful setting, this vacation rental offers a cozy and comfortable stay for guests looking to escape the hustle and bustle of everyday life. With well-appointed accommodations and a range of amenities, High Pocket Vacation Rental is the perfect home away from home for your next getaway. Whether you're looking to relax and unwind or explore the beautiful surroundings, this institution provides a welcoming and inviting atmosphere for all visitors.

MV Cloud House Vacation Rental is a premier real estate and travel agency located in the picturesque town of Tisbury, Massachusetts. Our agency specializes in providing luxurious vacation rental properties for those looking to experience the beauty of Martha's Vineyard. Nestled at 36 Burts Way, our properties offer stunning views, top-notch amenities, and unparalleled customer service. Whether you are looking for a cozy cottage for a romantic getaway or a spacious beachfront villa for a family vacation, MV Cloud House Vacation Rental has the perfect property for you. Book your dream vacation today and let us help you create memories that will last a lifetime.

The Calico Seahorse-Beach Vacation Rentals is a unique institution located at 90 White Horse Road in Plymouth, Massachusetts, United States. As a real estate and travel agency, we offer 7 beach-themed bungalows just a 5-minute walk from White Horse Beach. Each bungalow is a dream destination, fully furnished with everything you need for a beach getaway, including a beach wagon filled with chairs, umbrellas, and boogie boards, as well as an outdoor shower, community fire pit, and your own gas grill. Our accommodations include a Studio that sleeps 2, three 1-bedroom bungalows that sleep 5, two 2-bedroom bungalows that sleep 7, and a 4-bedroom Main house that sleeps 11. All of our bungalows are fully stocked with a kitchen, stainless steel appliances, drip coffee maker, and a Keurig. Each bungalow is themed after places we have traveled around the world, adding a colorful and whimsical touch to the property.

Nashaquisset is a charming village located on the beautiful island of Nantucket in Massachusetts. This idyllic getaway offers vacation rentals in the form of homes and cottages, perfect for those looking for a peaceful and relaxing retreat. Whether you are looking for a cozy cottage for a romantic getaway or a spacious home for a family vacation, Nashaquisset has a variety of options to suit your needs. As a lodging, real estate, and travel agency, we are dedicated to providing exceptional service to our guests and helping them create unforgettable memories on Nantucket. Visit us at 7 Washaman Avenue to start planning your dream vacation today.

Pilgrims Bliss Nantucket Vacation Home Rental is a luxurious and spacious accommodation located at 27 Pilgrim Road in Nantucket, Massachusetts, United States. This real estate and travel agency offers a main house and guest house that can accommodate up to 24 guests, making it perfect for large families or groups. The property features a heated salt water pool, a pond filled with ducks, a large yard, and is just a short stroll away from town and beaches. The newly updated "Pilgrim's Bliss" provides a unique combination of comfort and convenience, with a 6 bedroom main house and guest house, outdoor living areas, fireplaces, and a private flower-lined path leading to a peaceful pond. The property offers privacy from tall trees and hedges, creating a calm and luxurious setting for guests to enjoy.

Apple Tree Cape Cod Vacation Properties is a charming institution located at 40 Leilla Rich Drive in Wellfleet, Massachusetts, United States. As a park, real estate agency, and travel agency all rolled into one, we specialize in providing top-notch vacation properties for those looking to experience the beauty of Cape Cod. Our properties are nestled among the iconic apple trees of the region, offering a peaceful and serene setting for guests to relax and unwind. Whether you're looking for a cozy cottage for a romantic getaway or a spacious beachfront home for a family vacation, we have the perfect property for you. Let us help you create unforgettable memories on your next trip to Cape Cod.

Perfect Cape Escape, Vacation Rental is a charming retreat located at 4 Coffey Lane in Dennis, Massachusetts. This real estate and travel agency offers a bright and spacious open concept with 4 beautiful bedrooms, perfect for a relaxing getaway. The large entertaining deck overlooks the expansive backyard, complete with a stone fire pit and outdoor shower for ultimate relaxation. Situated just minutes away from Swan Pond, Main Street, and Nantucket Sound, this vacation rental is in the perfect location for exploring all that Cape Cod has to offer. The property is nestled in a quiet and friendly residential neighborhood, just off route 28. Guests can easily walk to kayaking on Swan Pond River or grab a coffee at Dunkin Donuts. Within a short drive, guests can enjoy the beautiful beaches of Dennis, such as South Village Beach and Sea Street Beach. Nearby convenience stores, shopping plazas, and a variety of shops make it easy to find everything you need for a comfortable stay.

Starfish Vacation Village is a charming seaside retreat located at 2032 U.S. 6 in Wellfleet, Massachusetts. Nestled in the heart of Cape Cod, this idyllic resort offers guests a peaceful and relaxing getaway surrounded by natural beauty. The village features cozy cottages, a sparkling swimming pool, and lush gardens, creating the perfect setting for a memorable vacation. Whether you're looking to unwind on the beach, explore the nearby hiking trails, or simply enjoy a quiet evening by the fire pit, Starfish Vacation Village has something for everyone. Come experience the magic of Cape Cod at this hidden gem on the coast.

Travel Vacations is a premier travel agency located at 46 Webster Avenue in Woburn, Massachusetts. We specialize in creating unforgettable vacation experiences for our clients, offering a wide range of services including booking flights, accommodations, tours, and transportation. Our team of experienced travel agents is dedicated to providing personalized and expert advice to help you plan the perfect getaway. Whether you're looking for a relaxing beach vacation, an adventurous safari, or a cultural exploration, Travel Vacations has you covered. Contact us today to start planning your dream vacation!

Italian Exclusive Vacation is a premier travel agency located in Waltham, Massachusetts, specializing in creating luxurious and unforgettable vacations to Italy. Our team of experienced travel experts is dedicated to crafting personalized itineraries that cater to the unique preferences and interests of each client. From exploring the historic streets of Rome to savoring the finest wines in Tuscany, we ensure that every aspect of your Italian getaway is meticulously planned and executed. Whether you seek a romantic honeymoon, a family adventure, or a solo retreat, Italian Exclusive Vacation is your gateway to experiencing the beauty, culture, and cuisine of Italy in style and comfort. Visit us at 24 Crescent Street to start planning your dream vacation today.

Magical Enchanted Vacations by Chrystine is a premier travel agency located at 67 Brand Avenue in Wilmington, Massachusetts. Specializing in creating unforgettable and enchanting travel experiences, our team of experts is dedicated to helping clients plan the vacation of their dreams. Whether you're looking to explore a magical Disney destination, relax on a tropical beach, or embark on a European adventure, we are here to make your travel dreams a reality. Contact us today to start planning your next magical getaway!

Dream Vacations- Sharon Hunt is a premier travel agency located at 1 North Avenue in North Attleborough, Massachusetts. Our dedicated team of travel experts is committed to helping you plan your dream vacation, whether it's a relaxing beach getaway, an adventurous safari, or a luxurious cruise. We offer personalized service, expert advice, and competitive pricing to ensure that your trip is unforgettable. Let us help you turn your travel dreams into reality at Dream Vacations- Sharon Hunt.

Jenn Erickson - Dream Vacations is a premier travel agency located at 456 Main Street in Wilmington, Massachusetts, United States. Our dedicated team of travel experts is committed to helping you plan your dream vacation, whether it be a relaxing beach getaway, an adventurous safari, or a romantic European escape. With personalized service and attention to detail, we strive to create unforgettable travel experiences for our clients. Contact us today to start planning your next dream vacation!

JMC Vacations is a premier travel agency located at 917 Pine Street in Raynham, Massachusetts, United States. Our team of experienced travel experts is dedicated to providing top-notch service and helping clients plan their dream vacations. Whether you're looking for a relaxing beach getaway, an adventurous mountain retreat, or a cultural city tour, we can help create the perfect itinerary tailored to your preferences. From booking flights and accommodations to arranging tours and activities, JMC Vacations is your one-stop shop for all your travel needs. Contact us today to start planning your next unforgettable vacation!

Salisbury Sea Breeze Vacation Homes in Salisbury, Massachusetts offers a collection of stunning vacation rental properties perfect for a seaside getaway. Located at 268A North End Boulevard, this real estate and travel agency specializes in providing guests with beautiful accommodations just steps away from the beach. Whether you're looking for a cozy cottage for a romantic retreat or a spacious beach house for a family vacation, Salisbury Sea Breeze Vacation Homes has the perfect property for you. Experience the beauty of the Massachusetts coastline and enjoy a relaxing stay at one of their charming vacation homes.

Merchant Vacations By Craine is a premier travel agency located at 423 Lancaster Avenue in Lunenburg, Massachusetts, United States. With years of experience in the travel industry, our team of experts is dedicated to creating unforgettable vacation experiences for our clients. Whether you're looking for a relaxing beach getaway, an adventurous mountain retreat, or a cultural city tour, we have the knowledge and resources to make your dream vacation a reality. Contact us today to start planning your next adventure with Merchant Vacations By Craine.

Seascape Vacation Rental Cape Cod is a premier real estate and travel agency located at 253 Old Wharf Road in Dennis, Massachusetts. Offering a wide selection of vacation rental properties in the picturesque Cape Cod area, Seascape is dedicated to providing guests with a memorable and relaxing getaway experience. With stunning ocean views, luxurious accommodations, and top-notch customer service, Seascape Vacation Rental Cape Cod is the perfect choice for those looking to escape the hustle and bustle of everyday life and immerse themselves in the natural beauty of the Cape Cod region. Book your dream vacation with Seascape today and create lasting memories that will last a lifetime.

Beach Road Vacation Rentals is a premier real estate and travel agency located at 41 Main Street in Orleans, Massachusetts. Our agency offers a wide selection of vacation rentals along the beautiful Beach Road, providing guests with the perfect accommodations for a relaxing and memorable getaway. Whether you're looking for a cozy beachfront cottage or a spacious vacation home with stunning ocean views, our experienced team is dedicated to helping you find the perfect rental for your needs. With our attention to detail and personalized service, Beach Road Vacation Rentals is your go-to destination for a dream vacation on the Cape Cod coast.

Holiday Vacation Condominiums is located at 488 Main Street in Yarmouth, Massachusetts, United States. Situated in West Yarmouth, HVC is centrally located to all the attractions that Cape Cod has to offer. Just minutes away from the historical towns of Dennis, Harwich, Hyannis, and Yarmouth, as well as the beautiful beach fronts, a stay at HVC guarantees that you will have the best opportunity to explore and enjoy all the beauty and entertainment that Cape Cod has to offer. Our One-Bedroom unit is perfect for those seeking a comfortable stay, while our charming Studio Unit is ideal for your next vacation. Click the link below to learn more about the nearby attractions and beaches for your next stay at The Holiday Vacation Condominiums.

A Summer Place Vacations LLC is a reputable real estate agency located in the picturesque town of Orleans, Massachusetts. Specializing in vacation rentals, they offer 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, their experienced team is dedicated to helping you find the perfect summer getaway. With a prime location near Eldredge Park Way, A Summer Place Vacations LLC is your go-to destination for a memorable and relaxing vacation on Cape Cod.

East Sandwich Luxury Vacation Rental is a premier real estate agency located at 11 Fort Hill Road in the charming town of Sandwich, Massachusetts. Our agency specializes in offering luxurious vacation rentals in the East Sandwich area, providing guests with top-notch accommodations and exceptional service. Whether you are looking for a beachfront property, a cozy cottage, or a spacious family home, we have a wide selection of rental options to choose from. With stunning views, upscale amenities, and a prime location near the beach, our vacation rentals are the perfect choice for a memorable getaway on Cape Cod. Book your stay with East Sandwich Luxury Vacation Rental and experience the ultimate in relaxation and comfort.