Luxury Vacation Rentals 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 vacation rentals – enter your dates for availability.
Dennis, Massachusetts
Wander Cape Cod Beach
Next avail.
Dec 8 - Dec 10
38
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
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 2 - Dec 4
47
5
Sweet deal
Salisbury, Connecticut
Wander Lakefront Retreat
Next avail.
Dec 3 - Dec 5
36
4.7
Chatham, Massachusetts
Wander Chatham Oasis
Next avail.
Dec 2 - Dec 8
712
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 2 - Dec 8
610
Gosnold, Massachusetts
Wander Cuttyhunk Waterfront
Next avail.
Dec 2 - Dec 4
48
Welcome to Massachusetts
Wander brings elevated comfort to New England with a portfolio that spans Cape Cod and the Berkshires. In Barnstable, Chatham, and Dennis, choose light-filled coastal homes designed for effortless living. In Becket, settle into modern woodland retreats that prize privacy and quiet. Our luxury vacation rentals in Massachusetts deliver the assurance of a five-star stay with the warmth of a private home.
Expect hotel-grade amenities, pristine cleaning, and 24/7 concierge in every stay, plus thoughtful touches like ultra fast WiFi, chef-ready kitchens, plush linens, and in many homes fitness spaces, pools, and smart controls. Arrive to inspiring views and a space that simply works for your life.
Destinations in Massachusetts
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
Sweet deal
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
Becket, Massachusetts
Wander Berkshires Lakeside
Next avail.
Dec 2 - Dec 4
510
Becket, Massachusetts
Wander Berkshires Lodge
Next avail.
Dec 2 - Dec 4
612
Stonington, Connecticut
Wander Stonington Peninsula
712
Dennis, Massachusetts
Wander Cape Cod Beach
Next avail.
Dec 26 - Dec 29
38
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
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 5 - Dec 8
47
5
Sweet deal
Salisbury, Connecticut
Wander Lakefront Retreat
Next avail.
Dec 5 - Dec 8
36
4.7
Gosnold, Massachusetts
Wander Cuttyhunk Waterfront
Next avail.
Dec 5 - Dec 8
48
East Falmouth, Massachusetts
Wander Falmouth Bay
Next avail.
Dec 12 - Dec 15
511
Sweet deal
Hillsdale, New York
Wander Hillsdale Valley
Next avail.
Dec 12 - Dec 15
410
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
Dennis, Massachusetts
Wander Cape Cod Beach
Next avail.
Dec 8 - Dec 10
38
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
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 2 - Dec 4
47
5
Sweet deal
Salisbury, Connecticut
Wander Lakefront Retreat
Next avail.
Dec 3 - Dec 5
36
4.7
Chatham, Massachusetts
Wander Chatham Oasis
Next avail.
Dec 2 - Dec 8
712
Barnstable, Massachusetts
Wander Cape Cod Estate
Next avail.
Dec 2 - Dec 8
610
Gosnold, Massachusetts
Wander Cuttyhunk Waterfront
Next avail.
Dec 2 - Dec 4
48
Discover more of Massachusetts
Sea breeze mornings on Cape Cod and sunset-kissed valleys in the Berkshires set a remarkable rhythm for any getaway. Swim and stroll the beaches of Dennis and Chatham, explore tidal flats and salt marshes, then linger in charming village centers with galleries and local flavor. Barnstable offers classic Cape character and easy access to the calm of the bay and open Atlantic.
Head west to Becket for forested trails, glassy lakes, and a vibrant arts scene anchored by Jacob’s Pillow. Summer brings festivals and scenic drives, autumn delivers radiant foliage, and winter means cozy fireside evenings. This is why Wander’s luxury vacation rentals in Massachusetts are the perfect choice, whether you’re traveling for work or leisure.