Large Group Vacation Rentals in Massachusetts
Book a Wander with inspiring views, hotel-grade amenities, modern workstations, top-tier cleaning and 24/7 concierge service. It’s a vacation home, but better.
Top-Rated Luxury Vacation Rentals in Massachusetts for Large Groups
Massachusetts combines historical charm with breathtaking landscapes, making it a top destination for group getaways. Wander’s properties in Massachusetts are designed to provide unforgettable experiences for large groups, blending luxury with thoughtful design. From Cape Cod’s sandy beaches to the serene Berkshires, our homes offer spacious layouts, cutting-edge amenities, and unparalleled comfort.
Luxury Vacation Rentals for Large Groups
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IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Only the top 1% of vacation homes are available on Wander.
Only the top 1% of homes
We’ll never not look like the pictures. We select homes in the most beautiful destinations and pour our hearts into making them magical so you can leave your stress at the door.
Hotel-grade amenities
We’ll never leave you with nothing to do. From workstations with super fast WiFi to gyms, pools, and saunas, our locations are set up for you to effortlessly blend work and play.
24/7 Concierge service
We’ll never leave you hanging. Our text-based Concierge is always available to help make your trip the best ever – from house questions to activity recommendations and more.
Inspiring and stunning views
We’ll never leave you uninspired. Every Wander is located in an incredible setting with stunning views that will have you feeling inspired and refreshed in no time. Adventure awaits.
Meticulous cleaning
We’ll never have you check in to a dirty house with crusty ketchup in the fridge. Our cleaning teams are meticulous about quality. We won't leave you a list of chores at check out either.
Safety and security
We’ll never pass you off to a stranger. All of the Wander locations on our platform are hand-picked by us and managed to our incredibly high, industry-leading safety standards.
A Guide to Luxury Travel for Large Groups in Massachusetts
Massachusetts offers a wealth of experiences for every type of traveler. Explore Cape Cod’s pristine beaches, hike the Berkshires, or immerse yourself in Boston’s rich history. Wander’s large group rentals put you in the heart of these adventures while ensuring unmatched comfort and convenience.
Whether you’re planning outdoor activities, cultural explorations, or simply relaxing, Massachusetts is a destination that caters to all.
When Should You Visit Massachusetts with a Large Group?
Massachusetts offers something special in every season, from vibrant spring blooms to cozy winter escapes. Plan your trip based on the activities and experiences that best suit your group.
Spring
Massachusetts comes alive in the spring, with blooming flowers and pleasant weather. Visit Cape Cod for whale watching or explore Boston’s historic Freedom Trail. Spring also marks the beginning of baseball season – catch a Red Sox game at Fenway Park for a quintessential New England experience.
Summer
Summer in Massachusetts means sandy beaches, waterfront dining, and outdoor adventures. Cape Cod and Martha’s Vineyard are perfect for enjoying coastal breezes, while the Berkshires offer scenic hiking trails and cultural events like Tanglewood concerts.
Fall
Fall transforms Massachusetts into a picturesque wonderland. Drive through the Berkshires to admire the vibrant foliage or visit local orchards for apple picking. Don’t miss Salem in October, where Halloween festivities captivate visitors from all over.
Winter
Massachusetts offers a magical winter experience with activities like skiing in the Berkshires or ice skating on Boston Common’s Frog Pond. Cozy up in a luxury rental with a roaring fire and watch the snow blanket the landscape.
Staying in the beautiful Berkshires? Read through our Wander Berkshires Retreat activities guide for some more itinerary inspiration. We also have an activities guide for Wander Cape Cod.
Types of Large Group Trips to Massachusetts
Whether you're reuniting with family, celebrating with friends, or hosting a corporate retreat, Massachusetts has the perfect setting. Explore the types of trips that suit your group’s needs and interests.
Vacation with Friends
Massachusetts is ideal for reconnecting with friends. Enjoy beach days in Cape Cod, explore craft breweries in Boston, or unwind in a spacious Berkshires retreat.
Bachelor or Bachelorette Party
Celebrate in style with a party to remember. From private homes with game rooms and hot tubs to vibrant nightlife in Boston, Massachusetts offers endless possibilities for your bachelor or bachelorette party.
Family Reunion
Create lasting memories with loved ones in a home designed for togetherness. Spacious kitchens, outdoor areas, and entertainment options make Wander properties perfect for family reunions.
Corporate Rental
Elevate your corporate stay with a luxury rental in Massachusetts. High-speed Wi-Fi, modern workstations, and inspiring views provide the ideal backdrop for productivity and team bonding.
Choosing a Large Group Vacation Rental in Massachusetts
Wander Berkshires Retreat: 6 bedrooms | 6.5 baths | 11 beds | Sleeps <14
Escape to Wander Berkshires Retreat, a secluded haven surrounded by lush forests. This luxurious property features an outdoor hot tub, a private steam room, and a fire pit for evenings under the stars. Inside, a sun-drenched solarium complements an entertainment-ready living area with a pool table, foosball, and a fully equipped wet bar.
Whether you’re relaxing in the on-site gym or enjoying the game collection, this retreat perfectly balances relaxation and recreation.
Wander Cape Cod: 7 bedrooms | 9 baths | 11 beds | Sleeps <16
Nestled near Nauset Beach, Wander Cape Cod blends coastal charm with modern luxury. This spacious property boasts a sparkling pool, a hot tub, and a BBQ area perfect for summer gatherings.
The stylish pool house includes games and an arcade, offering entertainment for all ages. Just a short stroll from private beach access, this home invites you to enjoy Massachusetts’s stunning shoreline in style.
Getting Around
Massachusetts’s compact size makes it easy to explore. Renting a car is the most convenient way to travel, whether you’re navigating Boston’s historic streets or venturing to the Berkshires. Wander properties are strategically located to provide both privacy and accessibility, ensuring a seamless experience throughout your stay.
See our Wander Berkshires Retreat transportation guide for more information on how to get to and from your rental seamlessly.
FAQs
What Amenities Can I Expect in Wander's Large Group Vacation Rentals in Massachusetts?
Wander’s Massachusetts homes feature premium amenities such as private pools, hot tubs, fully equipped kitchens, and spacious bedrooms. Concierge service and high-speed Wi-Fi ensure that every detail is covered.
What Makes Wander’s Large Group Rentals in Massachusetts Stand Out?
Our homes offer luxurious spaces in stunning locations, blending convenience with elegance. From top-tier cleaning standards to curated entertainment options, Wander’s large Massachusetts properties are crafted for exceptional experiences.
Are Your Large Rental Properties in Massachusetts Suitable for Hosting Gatherings or Events?
Absolutely! Whether it’s a family reunion, birthday celebration, or corporate retreat, our properties are designed to accommodate special occasions with ease.
