Luxury Vacation Rentals with a Private Pool 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 8 private pool vacation rentals – enter your dates for availability.
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
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
Egremont, Massachusetts
Wander Berkshires Serenity
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
Barnstable, Massachusetts
Wander Cape Cod Garden
Next avail.
Dec 2 - Dec 8
612
Welcome to private poolside luxury in Massachusetts
Make Cape Cod your private resort with Wander’s luxury private pool vacation rentals in Massachusetts. Our portfolio in Barnstable and Chatham features stylish coastal homes operated to five-star standards by our in-house team.
Every stay centers on a sparkling private pool for laid-back afternoons or refreshing morning laps. Expect ultra fast WiFi, work-friendly spaces, plush linens, pristine cleaning, and 24/7 concierge support. With hotel-grade amenities throughout, these homes make it effortless to blend productivity and relaxation in one beautiful setting.
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
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
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
Barnstable, Massachusetts
Wander Cape Cod Garden
Next avail.
Dec 2 - Dec 8
612
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
Edgartown, Massachusetts
Wander Martha's Vineyard
Next avail.
Dec 2 - Dec 4
47
5
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
Egremont, Massachusetts
Wander Berkshires Serenity
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
Barnstable, Massachusetts
Wander Cape Cod Garden
Next avail.
Dec 2 - Dec 8
612
Discover more beyond the pool in Massachusetts
Barnstable’s seven villages unfold from the historic lanes of Route 6A to Hyannis Harbor and the sweeping sands of Centerville and Craigville, with calm bays and steady breezes made for time on the water. Chatham charms with its working fish pier, Chatham Lighthouse, and the wild beaches of Monomoy National Wildlife Refuge where seals gather along shifting shoals.
Summer hums with boat outings and beach days, while autumn brings cranberry harvest colors and quieter shoreline walks. This coastal variety makes Cape Cod compelling year round, which is why Wander’s luxury private pool vacation rentals in Massachusetts are the perfect choice, whether you are traveling for work or leisure.