Luxury Vacation Rentals for Families 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 18 family vacation rentals – enter your dates for availability.
Salisbury, Connecticut
Wander Lakefront Retreat
Next avail.
Dec 3 - Dec 5
36
4.7
Sandwich, Massachusetts
Wander Cape Cod Beachfront
Next avail.
May 21 - May 27
36
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 2 - Dec 4
47
5
Dennis, Massachusetts
Wander Cape Cod Beach
Next avail.
Dec 8 - Dec 10
38
Gosnold, Massachusetts
Wander Cuttyhunk Waterfront
Next avail.
Dec 2 - Dec 4
48
Provincetown, Massachusetts
Wander Provincetown Shores
Next avail.
Dec 9 - Dec 15
48
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
Welcome to family adventures in Massachusetts
Bring the whole crew to a better kind of getaway. Our Massachusetts collection is built for space, privacy, and ease, with coastal homes in Barnstable, Chatham, and Dennis and a wooded escape in Becket for Berkshire calm. Every stay matches the photos and is professionally operated, so you can settle in without the guesswork.
Choose from luxury family vacation rentals in Massachusetts with multi-bedroom floor plans, expansive living rooms, chef-ready kitchens, ultra fast WiFi, and dedicated workspaces. Expect hotel-grade cleanliness, 24/7 concierge support, and thoughtful details that make traveling with kids feel effortless.
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 2 - Dec 4
510
4.6
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 2 - Dec 4
47
5
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
Salisbury, Connecticut
Wander Lakefront Retreat
Next avail.
Dec 5 - Dec 8
36
4.7
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 5 - Dec 8
47
5
Dennis, Massachusetts
Wander Cape Cod Beach
Next avail.
Dec 26 - Dec 29
38
Gosnold, Massachusetts
Wander Cuttyhunk Waterfront
Next avail.
Dec 5 - Dec 8
48
Barnstable, Massachusetts
Wander Cape Cod Village
Next avail.
Dec 5 - Dec 8
510
4.6
Yarmouth, Massachusetts
Wander Cape Cod Ocean
Next avail.
Dec 5 - Dec 8
510
5
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 12 - Dec 15
410
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 12 - Dec 15
511
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
Salisbury, Connecticut
Wander Lakefront Retreat
Next avail.
Dec 3 - Dec 5
36
4.7
Sandwich, Massachusetts
Wander Cape Cod Beachfront
Next avail.
May 21 - May 27
36
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 2 - Dec 4
47
5
Dennis, Massachusetts
Wander Cape Cod Beach
Next avail.
Dec 8 - Dec 10
38
Gosnold, Massachusetts
Wander Cuttyhunk Waterfront
Next avail.
Dec 2 - Dec 4
48
Provincetown, Massachusetts
Wander Provincetown Shores
Next avail.
Dec 9 - Dec 15
48
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
Discover more family fun in Massachusetts
Massachusetts rewards family time with variety. On Cape Cod, gentle beaches and tidal flats invite easy days by the water, while rail trails weave through pine forests. In the Berkshires, mountain views, glassy ponds, and winding trails set the tone for unplugged afternoons and brilliant autumn color.
From lighthouse-dotted coastlines to country roads lined with farm stands, the state offers four seasons of simple pleasures and standout scenery. Plan a trip that blends seaside mornings with hillside sunsets, all within one destination. This is why Wander's luxury family vacation rentals in Massachusetts are the perfect choice, whether you're traveling for work or leisure.