The Best Private
Villas in Massachusetts

Travel Guide | September 2025
Set your dates to see room prices:

1 An authentic, rustic luxurious little single family home in Old Town. All yours. (Marblehead)

An authentic, rustic luxurious little single family home in Old Town. All yours. An authentic, rustic luxurious little single family home in Old Town. All yours. An authentic, rustic luxurious little single family home in Old Town. All yours. 27+
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2 41 - 3BR Quincy - Lovely Townhouse near Adams (Quincy)

41 - 3BR Quincy - Lovely Townhouse near Adams 41 - 3BR Quincy - Lovely Townhouse near Adams 41 - 3BR Quincy - Lovely Townhouse near Adams 27+
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3 Cape Cod Villa (Harwich)

Cape Cod Villa Cape Cod Villa Cape Cod Villa 27+
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4 Harvrd-MIT-B.U./Parkfree/Single Family residence (Boston)

Harvrd-MIT-B.U./Parkfree/Single Family residence Harvrd-MIT-B.U./Parkfree/Single Family residence Harvrd-MIT-B.U./Parkfree/Single Family residence 27+
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5 Renovated & Sophisticated Home Near Beach & Shops! (Barnstable)

Renovated & Sophisticated Home Near Beach & Shops! Renovated & Sophisticated Home Near Beach & Shops! Renovated & Sophisticated Home Near Beach & Shops! 27+
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6 9 Green Hollow Road (Nantucket)

9 Green Hollow Road 9 Green Hollow Road 9 Green Hollow Road 27+
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7 Large, Comfortable & Conveniently located Home (Danvers)

Large, Comfortable & Conveniently located Home Large, Comfortable & Conveniently located Home Large, Comfortable & Conveniently located Home 27+
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8 Full House/Heart of Worcester (Worcester)

Full House/Heart of Worcester Full House/Heart of Worcester Full House/Heart of Worcester 27+
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9 56Beachway-Private beach Refreshed in 2022 Cozy (East Sandwich)

56Beachway-Private beach Refreshed in 2022 Cozy 56Beachway-Private beach Refreshed in 2022 Cozy 56Beachway-Private beach Refreshed in 2022 Cozy 27+
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10 Cambridge Boston 3BR2Bth Parking W&D Subway AC (Somerville)

Cambridge Boston 3BR2Bth Parking W&D Subway AC Cambridge Boston 3BR2Bth Parking W&D Subway AC Cambridge Boston 3BR2Bth Parking W&D Subway AC 27+
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11 Wedgewood Cottage (Barnstable)

Wedgewood Cottage Wedgewood Cottage Wedgewood Cottage 27+
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12 Gloucester Coastal Gem (Gloucester)

Gloucester Coastal Gem Gloucester Coastal Gem Gloucester Coastal Gem 27+
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13 Rustic-Chic Cottage with Yard and Grill - Near Hiking! (Northfield)

Rustic-Chic Cottage with Yard and Grill - Near Hiking! Rustic-Chic Cottage with Yard and Grill - Near Hiking! Rustic-Chic Cottage with Yard and Grill - Near Hiking! 27+
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14 Waterfront Oasis in Yarmouth, Cape Cod (Yarmouth)

Waterfront Oasis in Yarmouth, Cape Cod Waterfront Oasis in Yarmouth, Cape Cod Waterfront Oasis in Yarmouth, Cape Cod 27+
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15 Bayfront Plymouth Gem with Sunroom, Steps to Shore! (Plymouth)

Bayfront Plymouth Gem with Sunroom, Steps to Shore! Bayfront Plymouth Gem with Sunroom, Steps to Shore! Bayfront Plymouth Gem with Sunroom, Steps to Shore! 27+
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16 ~*30min to Downtown*~ THE COSMOPOLITAN (Boston)

~*30min to Downtown*~ THE COSMOPOLITAN ~*30min to Downtown*~ THE COSMOPOLITAN ~*30min to Downtown*~ THE COSMOPOLITAN 27+
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17 Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak (Hancock)

Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak 27+
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18 2 Minute Walk to Beach, Cape Cod Escape (Dennis Port)

2 Minute Walk to Beach, Cape Cod Escape 2 Minute Walk to Beach, Cape Cod Escape 2 Minute Walk to Beach, Cape Cod Escape 27+
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19 Charming home Centrally located in Worcester (Worcester)

Charming home Centrally located in Worcester Charming home Centrally located in Worcester Charming home Centrally located in Worcester 27+
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