Luxury Vacation Rentals for Large Groups in Massachusetts
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 12 large group vacation rentals – enter your dates for availability.
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 2 - Dec 4
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 2 - Dec 4
510
5
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 2 - Dec 8
610
Egremont, Massachusetts
Wander Berkshires Serenity
Next avail.
Dec 2 - Dec 4
510
Becket, Massachusetts
Wander Berkshires Lakeside
Next avail.
Dec 2 - Dec 4
510
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 5 - Dec 7
410
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 2 - Dec 4
511
Chatham, Massachusetts
Wander Chatham Oasis
Next avail.
Dec 2 - Dec 8
712
Welcome to your large group retreat in Massachusetts
Bring everyone together with our luxury vacation rentals in Massachusetts. In Barnstable and Chatham, coastal homes pair clean design with sprawling layouts suited to large groups. In Becket, Berkshires retreats offer privacy and room to spread out for reunions and retreats.
Homes are set up for groups with chef-ready kitchens, generous dining space, multiple suites, and indoor-outdoor lounges for unhurried time together. Expect hotel-grade cleaning, ultra fast WiFi, and 24/7 concierge, with select homes adding pools, hot tubs, gyms, and game rooms. For big gatherings, it is the rare blend of polish, comfort, and space.
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 2 - Dec 4
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 2 - Dec 4
510
5
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 5 - Dec 7
410
Becket, Massachusetts
Wander Berkshires Lakeside
Next avail.
Dec 2 - Dec 4
510
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 2 - Dec 4
511
Becket, Massachusetts
Wander Berkshires Lodge
Next avail.
Dec 2 - Dec 4
612
Stonington, Connecticut
Wander Stonington Peninsula
712
Chatham, Massachusetts
Wander Chatham Oasis
Next avail.
Dec 2 - Dec 8
712
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. Your best trip ever is just a few clicks away.
All homes in Massachusetts
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 2 - Dec 4
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 2 - Dec 4
510
5
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 2 - Dec 8
610
Egremont, Massachusetts
Wander Berkshires Serenity
Next avail.
Dec 2 - Dec 4
510
Becket, Massachusetts
Wander Berkshires Lakeside
Next avail.
Dec 2 - Dec 4
510
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 5 - Dec 7
410
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 2 - Dec 4
511
Chatham, Massachusetts
Wander Chatham Oasis
Next avail.
Dec 2 - Dec 8
712
Discover more large groups activities in Massachusetts
Cape Cod delivers sweeping beaches, tidal flats, and classic New England seascapes. Barnstable and Chatham offer calm coves, lighthouse views, and breezy days on the water. Summer is lively, while spring and fall are serene and sunlit.
West in the Berkshires, Becket trades sea salt for mountain air. Lakes, trailheads, and stages like Jacob's Pillow set the tone in warm months, while nearby ski areas keep the season going when the snow arrives. With four distinct seasons, every visit feels different. This is why Wander's luxury vacation rentals in Massachusetts are the perfect choice, whether you're traveling for work or leisure.