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 14 large group vacation rentals – enter your dates for availability.
Chatham, Massachusetts
Wander Cape Cod Dunes
Next avail.
Dec 20 - Dec 22
614
Dennis, Massachusetts
Wander Cape Cod Haze
Next avail.
Dec 20 - Dec 22
614
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 20 - Dec 22
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 20 - Dec 22
510
5
Stonington, Connecticut
Wander Stonington Peninsula
712
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 20 - Dec 26
610
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 20 - Dec 22
511
Egremont, Massachusetts
Wander Berkshires Serenity
Next avail.
Jan 12 - Jan 14
510
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.
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 20 - Dec 22
510
5
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 20 - Dec 22
510
4.6
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Jan 26 - Jan 28
410
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 20 - Dec 22
511
Becket, Massachusetts
Wander Berkshires Lodge
Next avail.
Dec 21 - Dec 23
612
Becket, Massachusetts
Wander Berkshires Lakeside
Next avail.
Jan 4 - Jan 6
510
Chatham, Massachusetts
Wander Cape Cod Dunes
Next avail.
Dec 20 - Dec 22
614
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 20 - Dec 26
610
Chatham, Massachusetts
Wander Cape Cod Dunes
Next avail.
Jan 2 - Jan 5
614
Dennis, Massachusetts
Wander Cape Cod Haze
Next avail.
Jan 2 - Jan 5
614
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Jan 9 - Jan 12
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Jan 9 - Jan 12
510
5
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Jan 9 - Jan 12
511
Egremont, Massachusetts
Wander Berkshires Serenity
Next avail.
Jan 30 - Feb 2
510
Becket, Massachusetts
Wander Berkshires Lakeside
Next avail.
Jan 30 - Feb 2
510
Great Barrington, Massachusetts
Wander Berkshires Highlands
Next avail.
Jan 30 - Feb 2
612
Highlights in Massachusetts
Discover American history, vibrant city life, and scenic coastlines with a wide array of attractions perfect for entertaining large groups.
Freedom Trail
Faneuil Hall Marketplace
Cape Cod National Seashore
Plimoth Patuxet Museums
Historic Salem
Fenway Park
Tanglewood
Whale Watching from Gloucester
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
Chatham, Massachusetts
Wander Cape Cod Dunes
Next avail.
Dec 20 - Dec 22
614
Dennis, Massachusetts
Wander Cape Cod Haze
Next avail.
Dec 20 - Dec 22
614
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 20 - Dec 22
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 20 - Dec 22
510
5
Stonington, Connecticut
Wander Stonington Peninsula
712
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 20 - Dec 26
610
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 20 - Dec 22
511
Egremont, Massachusetts
Wander Berkshires Serenity
Next avail.
Jan 12 - Jan 14
510
Most popular amenities for large group vacation rentals in Massachusetts
More popular large group destinations in Massachusetts
Other popular amenities & vacation types in Massachusetts
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.
FAQs: Vacation Rentals in Massachusetts
Why should I book a Wander in Massachusetts over other large group vacation rentals?
Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.
Every home in Massachusetts delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?
Which are Wander’s most popular large group vacation rentals in Massachusetts?
Some of our most popular large group vacation rentals in Massachusetts include Wander Cape Cod Ocean, Wander Cape Cod Village, and Wander Hillsdale Valley. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.
How many different large group vacation rentals does Wander have available in Massachusetts?
Wander offers 14 large group vacation rentals in Massachusetts, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.
What time is check-in and check-out at Wander’s large group vacation rentals in Massachusetts?
You can check-in to Wander large group vacation rentals in Massachusetts after 4.00pm and check-out before 10.00am.
Do Wander’s large group vacation rentals in Massachusetts have WiFi access?
Yes. Every Wander home in Massachusetts has ultra fast, reliable WiFi so you can stay connected throughout your stay.
What is Wander’s cancellation policy?
You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.