North Eastham

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Sweet cottage nestled in scenic Drummer's Cove (CS0052)

Wellfleet, Massachusetts

2 bedrooms•1 baths

Newly offered. Private beach, guest cottage and large yard (RPMS173)

Hyannis, Massachusetts

6 bedrooms•4.5 baths

$18,567for 7 nights•Sep 19 – Sep 26

Private Orleans Getaway Near Bakers Pond & Beaches (2422)

5.0 (4)

Orleans, Massachusetts

4 bedrooms•3 baths

$1,738for 3 nights•Sep 24 – Sep 27

Welcome to View Point ! One of a kind Chatham estate. RPMS178

Chatham, Massachusetts

8 bedrooms•9.5 baths

Relaxing Cape Cod Stay in a Charming Osterville Setting RPAM121

Osterville, Massachusetts

2 bedrooms•2 baths

Stunning Waterfront Property Overlooking Pleasant Bay (2327)

4.3 (3)

Harwich, Massachusetts

3 bedrooms•3 baths

Quiet Neighborhood .2 miles to Skaket Beach (1193)

Orleans, Massachusetts

2 bedrooms•2.5 baths

The Iconic Wharf House - Your Own P-Town Paradise RPAM116

Provincetown, Massachusetts

1 bedroom•2 baths

$4,923for 4 nights•Sep 26 – Sep 30

Expansive Home by Orleans Town Landing (1086)

5.0 (6)

Orleans, Massachusetts

4 bedrooms•2.5 baths

Stunning Falmouth estate with heated pool and gardens RPMS177

Falmouth, Massachusetts

6 bedrooms•6 baths

Home on Great Island overlooking Nantucket Sound with Private Beach (1199)

4.6 (5)

West Yarmouth, Massachusetts

4 bedrooms•3 baths

$5,005for 7 nights•Sep 26 – Oct 3

Close to Beach, Harbor Out Front, Village Around the Corner! RPAM122

Harwich Port, Massachusetts

4 bedrooms•3.5 baths

$5,368for 4 nights•Oct 13 – Oct 17

New for 2026. Great Osterville location! RPMS167

Osterville, Massachusetts

4 bedrooms•2.5 baths

Coastal home in Brewster near beaches and bike path RPMS161

Brewster, Massachusetts

3 bedrooms•3.5 baths

Quintessential Cape Cod home on Great Pond RPLO026

Teaticket, Massachusetts

4 bedrooms•3 baths

$8,462for 7 nights•Sep 19 – Sep 26

Plan Ahead

Everything you need for your stay

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